Chester vacation rentals

We found 1,644 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:Jun 12 - Jun 19

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Property grounds
10 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)

Reading Farms Estate

Reading

22% off
Price is $3,107
$21,750 for 7 nights
All fees included
Reading Farms Estate

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Find out more about Chester

Why visit Chester

  • Outdoor adventures: Chester is perfect for outdoor enthusiasts, offering skiing, kayaking, and hiking experiences.
  • Stunning landscapes: Explore breathtaking craggy peaks and serene central Vermont scenery.
  • Charming small-town atmosphere: Enjoy the friendly vibe and cultural experiences unique to Chester.
  • Diverse accommodations: Choose from cozy vacation homes, stylish condos, or charming cabins for a comfortable stay.
  • Family-friendly activities: Visit Chester Park and explore local landmarks for enjoyable family outings.

Popular types of accommodation in Chester

Chester offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for a cozy private vacation home, a stylish condo, or one of the best Chester cabins, you'll find the perfect spot to unwind. With numerous options available, including charming cabins for rent and comfortable Chester hotels, your ideal getaway is just a click away. Explore all that Chester has to offer and make your vacation truly memorable.

  • Houses: The top choice for visitors in Chester, these homes offer spacious and comfortable stays, perfect for families and groups.
  • Condos: A popular option for travelers seeking convenience and amenities, condos provide a blend of comfort and accessibility.
  • Cabins: Ideal for those wanting a rustic experience, cabins in Chester offer a cozy retreat surrounded by nature.
  • Apartments: A practical selection for short stays, apartments provide a home-like atmosphere with essential facilities.
  • Chalets: These charming lodgings combine alpine style and comfort, making them a delightful choice for visitors.**

Top attractions in and around Chester

Chester, Vermont, is an ideal destination for outdoor enthusiasts and families, offering a variety of adventures from skiing to friendly hikes. Explore stunning craggy peaks, enjoy kayaking experiences, and relax at Chester Park. The area features captivating landmarks and state parks, making it perfect for cultural experiences and family outings. Don't forget to check out local houses for rent for a comfortable stay while you discover all that Chester has to offer.

  • Bonnie's Bundles Dolls: A charming attraction in Chester, offering a unique collection of handcrafted dolls that exude romantic vibes. Visitors can explore the artistry and craftsmanship behind each creation, making it a delightful stop for doll enthusiasts and collectors.
  • Lake Rescue: Located 14 miles from Chester, this picturesque lake is perfect for outdoor activities and romantic getaways. Enjoy scenic views, a relaxing beach atmosphere, and opportunities for swimming, fishing, and picnicking.
  • Jamaica State Park: Just 13 miles away, this national park features stunning scenery and a range of outdoor adventures. Hike through beautiful trails, discover waterfalls, and embrace the natural beauty of Vermont.

Things to do recommended for couples

Chester, Vermont, offers charming experiences for couples. Enjoy a scenic hike at the nearby Green Mountain National Forest, then unwind with a cozy dinner at a local eatery. Don't miss exploring the quaint shops and galleries in town for a delightful afternoon together.

Things to do recommended for families

Families visiting Chester, Vermont, can explore the scenic beauty of Okemo Mountain Resort, enjoy hiking trails suitable for all ages, and visit the local farmers' market for fresh produce and crafts. Don't miss the fun at the nearby Splashdown Park for a splash-tastic day.

Things to do recommended for groups

Explore the scenic Chester Village with its charming shops and eateries, or embark on a thrilling hike in the nearby Green Mountain National Forest. For a unique experience, consider a group visit to the local farmers' market for fresh produce and artisan goods.

*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 planning your trip—whether you're traveling with a group, enjoying quality time with family, bringing along your pets, or seeking extended stays—be sure to prioritize your preferences while filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chester with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chester with young kids: Traveling with young kids can present some challenges. It’s important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities, 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 families, a trip just isn’t the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Chester: If you're in search of vacation rentals with special offers 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 preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation, making it perfect for ski enthusiasts and budget travelers alike. Explore the charming small-town atmosphere, with nearby cities showcasing luxury and historical vibes. From the serene landscapes of central Vermont to friendly locals, your visit promises a memorable experience in this picturesque region.

  • Ludlow: Ludlow is a charming city located 11 miles from Chester, offering visitors a perfect blend of outdoor adventure and small-town charm. Known for its excellent skiing opportunities, Ludlow is home to the popular Okemo Mountain Resort, where visitors can hit the slopes or enjoy snowboarding during the winter months. In addition to winter sports, the area features stunning lakes and mountains ideal for hiking and other outdoor activities in the warmer seasons. The nearby state park provides opportunities for camping and exploring nature, making Ludlow a year-round destination for adventure seekers.
  • Springfield: Located a mere 6 miles from Chester, Springfield is a vibrant city that attracts travelers looking for an adventurous getaway. Like its neighboring towns, Springfield is renowned for its ski resorts and outdoor sports, making it a great spot for winter enthusiasts. Visitors can explore the scenic landscapes that encompass lakes and rolling mountains, perfect for hiking and picnicking during the summer months. The community offers a variety of local shops and restaurants, adding to the charm and experience of exploring this delightful New England town.
  • Andover: Andover, a quaint village within the Chester area, is an ideal destination for those seeking a peaceful retreat with plenty of adventure. Just a short distance from Chester, Andover invites travelers to enjoy skiing and outdoor sports. Surrounded by picturesque lakes and majestic mountains, visitors can take in breathtaking views while hiking or enjoying water activities. The unique archipelago nearby provides additional exploration opportunities for nature lovers. Andover’s small-town atmosphere and access to outdoor recreation make it a hidden gem for a relaxing yet adventurous 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 simple

Are you hoping to cut costs on your upcoming travel? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, consider booking a longer stay, which can lead to considerable savings. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to narrow down options by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash on eligible bookings. Sign up today to start enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient space for you to plan new trips, manage your ongoing plans, and organize your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the 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.

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