Chester vacation rentals

We found 1,636 vacation rentals — enter your dates for availability

Discover a selection of 35 homes, 10 cabins, and other vacation rentals in Chester that are perfect for your trip. Vacation rentals offer the best amenities for you and your friends, family, or even pets, such as parking and a fireplace. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Chester

Showing deals for:May 22 - May 29

Image gallery for "The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Exterior
9.8 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Plymouth

8% off
Price is $432
$3,022 for 7 nights
All fees included
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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Find out more about Chester

Why visit Chester

  • Outdoor Activities: Chester is perfect for ski enthusiasts and adventure seekers, offering a range of winter sports and summer activities.
  • Rich History: Explore local museums and historical sites that showcase Chester's charming past.
  • Scenic Landscapes: Enjoy the stunning natural beauty surrounding Chester, ideal for hiking, biking, and relaxation.
  • Cozy Accommodations: Choose from a variety of lodging options, including charming cabins and private vacation homes.
  • Family-Friendly Atmosphere: Chester provides a welcoming environment for families and friends to create lasting memories together.

Popular types of accommodation in Chester

If you're planning a getaway to Chester, you'll find a variety of accommodations to suit your needs. The most popular options include houses, cozy condos, and charming cabins. Whether you're searching for house rentals, a spacious bedroom apartment, or quaint cottages, our platform has everything you need to make your stay comfortable and memorable. Discover the perfect vacation rental in Chester today.

  • Houses: The top choice for travelers to Chester, these homes offer a comfortable and personalized stay, ideal for families or groups.
  • Condos: A popular second option, condos provide modern amenities and often stunning views, perfect for a relaxing getaway.
  • Cabins: Offering a charming escape, cabins are a favorite for those seeking a rustic experience surrounded by nature.
  • Apartments: These versatile accommodations are a great choice for solo travelers or couples looking for convenience and comfort.
  • Chalets: The fifth option, chalets provide a cozy atmosphere with a touch of mountain charm, perfect for a scenic retreat.**

Top attractions in and around Chester

Chester, Vermont, is an ideal destination for ski enthusiasts and adventure seekers alike. Visitors can explore a variety of attractions, including parks, state parks, and history museums, offering outdoor activities and cultural experiences. Whether you're traveling with family or friends, Chester provides an excellent blend of sports and exploration opportunities, ensuring a memorable vacation for everyone.

  • DaVallia Art & Accents: This charming gallery in Chester showcases a diverse collection of local art, offering a cultural experience that highlights the creativity of Vermont artists. You can find unique pieces that reflect the region's artistic spirit.
  • Lowell Lake State Park: Located 9 miles from Chester, this park is perfect for outdoor enthusiasts. Enjoy hiking, fishing, and breathtaking scenery, all while surrounded by lush forests and tranquil waters, making it an ideal spot for adventure.
  • Bonnie's Bundles Dolls: Situated in Chester, this delightful attraction features enchanting handcrafted dolls, perfect for collectors and gift-givers. The romantic ambiance invites visitors to explore the artistry and nostalgia of these charming creations.

Things to do recommended for couples

Chester offers charming couple experiences like skiing at Okemo Mountain Resort, just 11 miles away, or enjoying a scenic flight at Morningside Flight Park, 12 miles away. Don't forget the thrill of the South Face Express Ski Lift, also 12 miles from Chester, for an adventurous day together.

Things to do recommended for families

Your family will have a blast in Chester, Vermont. Enjoy ice skating at The Ice House, unleash your adventurous side at Maple Lanes arcade, and experience the thrill of the Timber Ripper Mountain Coaster, all within a short drive from town.

Things to do recommended for groups

Groups visiting Chester, Vermont can enjoy a trip to the Vermont Country Store for unique local goods, catch a show at the charming Weston Playhouse, and challenge each other at the scenic Fox Run Golf Course for a day of outdoor fun.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chester

When traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Chester with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group activities. Luckily, you can easily filter for these options and many others on Vrbo.
  • Traveling to Chester with young kids: Traveling with young children can present some challenges. It's important to prioritize their comfort and safety, as well as to look for amenities that are suitable for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chester: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you're searching for vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chester

Chester, Vermont, offers an inviting blend of adventure and relaxation for travelers. With its stunning landscapes, it's perfect for outdoor enthusiasts and families seeking a memorable getaway. Explore charming neighborhoods that exude historical vibes or indulge in luxury accommodations. Whether you're hitting the slopes or enjoying the local atmosphere, Chester provides a diverse experience that caters to every budget and preference. Discover the magic of this picturesque town on your next vacation.

  • Ludlow: Located 11 miles from Chester, Ludlow is a bustling destination for outdoor enthusiasts and sports lovers. Known for its incredible ski resorts, including Okemo Mountain Resort, Ludlow attracts visitors looking for adventure on the slopes and in the surrounding wilderness. The picturesque landscape features stunning lakes, majestic mountains, and serene valleys, making it a perfect backdrop for a range of activities year-round. Whether you're hitting the ski trails in winter or hiking in the warmer months, Ludlow offers an unforgettable travel experience.
  • Springfield: Just 6 miles from Chester, Springfield is another gem for those seeking outdoor adventure. This city is well-known for its ski fields and resorts, making it a popular choice for winter sports enthusiasts. Visitors can explore the nearby national state park, which offers breathtaking views and numerous trails for hiking and biking. With its lakes and mountains nearby, Springfield promises a vibrant atmosphere filled with recreational opportunities and scenic beauty, appealing to both thrill-seekers and nature lovers alike.
  • Grafton: Also located 6 miles from Chester, Grafton is a charming town that emphasizes outdoor experiences. Renowned for its ski resorts and fields, it provides ample opportunities for winter sports. Grafton is nestled among beautiful valleys and mountains, offering a tranquil escape into nature. Visitors can enjoy the stunning lakes and picturesque scenery while participating in various outdoor activities, from skiing in the winter to hiking and biking during the warmer seasons. Grafton’s quaint charm and natural beauty make it a delightful stop on your vacation.

Best time to go to Chester

If you're planning a trip to Chester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowModerately High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowModerately High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageModerately Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageModerately Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighModerately Low
October48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
November36.1°F (2.3°C)Light RainMostly SunnyAverageAverage
December27.3°F (-2.6°C)Light RainMostly CloudyAverageModerately High

Booking with Vrbo is a breeze

Are you hoping to save money on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy even greater savings. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and receive OneKeyCash on the full booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying the savings.

Vrbo Trips: Planning as easy as it gets

Experience the convenience of Vrbo's unique Trip Board, which offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access properties you've previously saved or booked, now organized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

A slice of New England in Chester

With its red-brick buildings and characterful high street, Chester embodies everything that’s great about America’s New England communities. It’s now listed on the National Register of Historic Places, which makes it a great place to discover history, culture, and the Vermont countryside. The atmosphere is unique, so why not stay local with downtown Chester vacation rentals housed in beautifully renovated Victorian buildings? Beyond its downtown charm, Chester serves as the gateway to Okemo Mountain Resort, as well as some of Vermont’s most beautiful national forests.

Turn back time in Chester’s Stone Village

Chester is best known for its Stone Village Historic District, where you can wander along streets lined with greyscale granite homes. Downtown, you’ll find the Chester Village Historic District, showcasing a medley of Victorian, Colonial Revival, and Federal style architecture. From 19th-century stone cottages to wood-paneled carriage houses, Chester vacation rentals give you a chance to live and breathe history. Why not continue the theme with a ride on the Green Mountain Railroad, which steams past rising mountains, sparkling rivers, and historic towns?

Get the adrenalin pumping on Okemo Mountain

Rising above the nearby village of Ludlow, Okemo Mountain Resort is a 4-season outdoor playground. In winter, the mountain serves up some of Vermont’s best downhill skiing. When the snow melts Okemo’s Adventure Zone offers everything from ziplining and rock-climbing to segwaying and mountain biking. If you’re serious about your par, Okemo boasts a pair of 18-hole championship golf courses complete with spectacular mountain vistas. Just 45 minutes away, Manchester is a popular day trip. From touring the grand Hildene Estate to visiting the American Museum of Fly Fishing, the town is full of quirks.

Chester’s the gateway to Okemo Mountain Resort

Winter is arguably high season in Chester, when flocks of skiers descend on Okemo Mountain Resort. Planning a ski break in Vermont? Chester vacation rentals unlock access to a huge selection of properties just minutes from Okemo Mountain. From cozy log cabins to luxurious family-style farmhouses, you can create your very own apres ski scene. Visit in fall and Chester is showered in reds, yellows, and golds. Spring brings perfect weather for outdoor pursuits, especially if you’re planning on hiking Okemo Mountain.

Mountains, forests, and Finger Lakes Fishing

Towering over 3000 feet high, Okemo Mountain dominates the landscape. If you’d rather escape the crowds, you’ll find off-the-beaten-track hiking trails in nearby state forests like Okemo and Proctor Piper. Hawks Mountain Wildlife Management Area is another backcountry favorite, with the chance to spot black bears and white-tailed deer. Both the Green Mountain National Forest (GMNF) and the Finger Lakes National Forest (FLNF) offer some of the state’s best fishing, though you’ll need to pick up a license before you cast a line.

Traveling to and around Chester

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Lebanon, NH (LEB-Lebanon Municipal), which is 28.8 mi (46.4 km) away.

Frequently asked questions

What is the best area to stay in Chester, Vermont, United States of America when booking a vacation rental?
When looking for the best area to stay in Chester, Vermont for a vacation rental, consider the charming downtown area. This neighborhood offers a delightful blend of historic character and modern amenities, making it a fantastic choice for visitors. The picturesque streets are lined with quaint shops, cozy cafes, and local eateries, providing ample opportunities to explore and enjoy the local culture.

One of the top attractions nearby is the iconic Chester Village Green, a lovely park that often serves as a hub for community events and gatherings. Additionally, the nearby Chester Historical Society offers fascinating insights into the town's rich history, making it a great stop for those interested in the area's heritage.

Another appealing option is the outskirts of Chester, where you can find beautiful properties located in nature, great for those seeking a more tranquil escape. This area provides easy access to outdoor activities such as hiking and skiing, with scenic trails and slopes just a short drive away.

Overall, Chester boasts a variety of vacation rental options, from charming cabins to cozy homes, suiting different preferences and group sizes.
How much does it cost to rent a vacation home in Chester?
Prices for vacation rentals in Chester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chester vacation house rentals?
You can find great discounts on house rentals in Chester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Chester ski resort rentals?
For the best ski resort rentals in Chester, Vermont, travelers should consider properties located in the nearby Okemo Mountain area, which is only a short drive away. The town of Ludlow serves as a popular base, offering a variety of vacation rentals that cater to ski enthusiasts. Many of these accommodations feature amenities such as cozy fireplaces, ski-in/ski-out access, and spacious living areas, making them superb for families or groups looking to unwind after a day on the slopes.

In addition to Ludlow, the quaint village of Chester itself provides charming options, including historic homes and rustic cabins that often come with modern conveniences like full kitchens, outdoor decks, and hot tubs. These properties allow visitors to enjoy a peaceful retreat while still being within reach of the ski resorts.

Moreover, the surrounding area boasts beautiful winter scenery, with opportunities for snowshoeing and cross-country skiing. Local shops and restaurants in Chester add to the experience, allowing guests to explore the town's unique character and enjoy the warm hospitality of this Vermont community.
Are there any family house rentals in Chester?
In Chester, Vermont, families will find a variety of vacation rentals, with around 35 suitable options available. The town offers a charming atmosphere, surrounded by the picturesque Green Mountains, making it an excellent destination for family getaways. Many homes provide spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy themselves.

Visitors can expect amenities such as cozy fireplaces, game rooms for entertainment, and sometimes even hot tubs for relaxation after a day of outdoor activities. The nearby Okemo Mountain Resort is superb for skiing in the winter, while warmer months invite families to explore local hiking trails, lakes for swimming, and the scenic beauty of the area.
Can I rent a vacation home with a pool or hot tub in Chester?
In Chester, Vermont, there are several vacation homes available for rent that feature pools and hot tubs. This charming town, located in the Green Mountains, offers a serene backdrop for visitors seeking relaxation and outdoor activities. Many of the rentals come with private pools or hot tubs, providing a superb space to unwind after a day of exploring the area.

Travelers can expect a variety of amenities in these properties, including fully equipped kitchens for home-cooked meals, cozy living spaces, and outdoor areas for enjoying the picturesque surroundings. The town's proximity to ski resorts and hiking trails makes it an ideal destination for both winter sports enthusiasts and summer adventurers.
Can I find long-stay vacation rentals in Chester?
A long-stay vacation rental in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chester?
In Chester, Vermont, there are several pet-friendly house rentals available, offering a range of amenities to accommodate travelers with furry companions. Many of these vacation homes feature spacious layouts, fully equipped kitchens, and outdoor areas such as decks or patios where pets can enjoy the fresh air.

The town is surrounded by beautiful natural scenery, superb for outdoor activities with pets. Nearby, you can find hiking trails and access to the Green Mountain National Forest, providing ample opportunities for exploration and adventure. Additionally, the charming village center offers pet-friendly cafes and shops, enhancing the overall experience for those traveling with pets.
Are there any remote work vacation rentals in Chester?
In Chester, Vermont, there are numerous remote work-friendly vacation rentals available, with around 49 properties to choose from. Many of these accommodations come equipped with essential amenities for remote work, including high-speed internet and designated workspaces featuring desks and chairs. Travelers can expect a comfortable environment conducive to productivity, often with free Wi-Fi access throughout the property.

The charming town of Chester offers a picturesque setting, with nearby attractions such as the quaint Chester Village and the scenic Green Mountain National Forest. Guests can enjoy the beauty of the natural landscape during breaks, with opportunities for outdoor activities like hiking and exploring local parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chester with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chester?
In Chester, popular vacation rental amenities include kitchens, which allow travelers to prepare their own meals, and decks or patios for enjoying the fresh Vermont air and picturesque views. Many rentals also feature fireplaces, providing a cozy atmosphere during colder months. Onsite parking is commonly available, making it easy for guests to explore the surrounding areas. Additionally, most properties come equipped with coffee and tea makers, ensuring that guests can start their day with a warm beverage.
When is the best time to visit Chester for a vacation rental?
The best time to book a vacation rental in Chester, Vermont, is during the vibrant fall month of September. This period marks the peak season for visitors drawn to the stunning autumn foliage and the charming New England atmosphere. As summer transitions into fall, you'll find plenty of outdoor activities, from hiking along picturesque trails to exploring local craft fairs and farmers' markets, all set against a backdrop of brilliant red, orange, and yellow leaves.

The temperatures in September generally range from the mid-50s to mid-70s Fahrenheit, ensuring comfortable conditions for sightseeing and enjoying the beautiful landscapes. This makes it an ideal time to stroll through the quaint village center, where you can admire historic architecture and discover local shops and eateries.

For those looking for a more budget-friendly option, consider planning your visit in March. While this month is quieter, it offers a great experience with winter activities still available, such as skiing and snowshoeing in nearby resorts, along with the tranquility of fewer crowds.

Ultimately, your choice will depend on whether you prefer the vibrant energy of the fall season or the peacefulness of early spring.
How early should I book a Chester vacation rental?
Book your Chester vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chester, Vermont, United States of America?
In Chester, Vermont, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historic charm. The picturesque town center features beautifully preserved buildings and quaint shops, making it a delightful place to explore on foot. Nearby, the Chester Depot offers a glimpse into the town's rail history and hosts seasonal events.

For outdoor enthusiasts, the surrounding Green Mountains provide excellent opportunities for hiking, biking, and enjoying the stunning fall foliage. The nearby Okemo Mountain Resort is a popular destination for skiing and snowboarding in the winter months, while the summer months offer mountain biking and golf.

Additionally, the scenic Vermont countryside is dotted with charming farms and local artisans, making it easy to find fresh produce and unique handmade goods. The town's proximity to the larger towns of Ludlow and Weston also allows visitors to access more dining and cultural experiences, including the Weston Playhouse Theatre Company.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

Frequently asked questions

Are there vacation rentals in Chester?
Yes, there are vacation rentals in Chester near Bonnie's Bundles Dolls, or you can select a more remote option if you want a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffeehouses and restaurants.
How many vacation rentals will I find in Chester?
Choose from 35 Expedia vacation rentals in Chester for a memorable vacation.
What's there to see and do in Chester?
Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of family-friendly sights. While in the area, you can also visit popular places like Stratton Mountain Resort and Okemo Mountain Resort.
What's a vacation rental in Chester like?
Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.

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