Chester vacation rentals

We found 1,578 vacation rentals — enter your dates for availability

Discover a selection of 34 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:Mar 6 - Mar 13

Image gallery for Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Fully stocked kitchen with plenty of room to prepare a family dinner
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester, VT

10% off
Price is CA $633
CA $5,968 total
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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Find out more about Chester

Why visit Chester

  1. Outdoor Adventure: Enjoy a variety of activities like skiing and hiking in the beautiful natural surroundings of Chester.
  2. Charming Accommodations: Choose from an array of cozy cottages, rustic cabins, and spacious vacation homes for a comfortable stay.
  3. Cultural Exploration: Discover local art and culture in nearby towns, enhancing your experience of the region.
  4. Family-Friendly Attractions: Engage in activities suitable for all ages, making it perfect for family vacations.
  5. Relaxing Atmosphere: Unwind in Chester’s serene environment, ideal for both adventure seekers and those looking to relax.

Popular types of accommodation in Chester

Planning a getaway to Chester? You're in for a treat! Discover the charm of this picturesque locale with a variety of vacation rentals, including houses, cozy condos, and rustic cabins. Whether you’re seeking a cottage retreat or a spacious vacation home, Chester has the perfect accommodation to suit your needs. Enjoy the beauty and serenity of this beautiful destination while enjoying the comforts of home.

  • Houses: The top choice for visitors to Chester, offering spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Condos: A popular option for those wanting modern amenities and a community atmosphere, ideal for couples and small families.
  • Cabins: Perfect for a rustic getaway, these charming retreats immerse you in nature while providing a cozy atmosphere.
  • Apartments: A practical choice for solo travellers or couples, offering the convenience of home in a vibrant setting.
  • Chalets: These picturesque lodgings provide a unique alpine experience, blending comfort with stunning mountain views.**

Top attractions in Chester

Chester, Vermont is a fantastic destination for those seeking ski and adventure vacations. With a variety of outdoor activities, cultural experiences, and family-friendly attractions, visitors can explore national and state parks, as well as local landmarks. Whether you're hitting the slopes or enjoying the local scenery, Chester offers a perfect blend of adventure and relaxation for all travellers.

  1. Baltimore Covered Bridge: This historic bridge, located 11.3km from Chester, offers a glimpse into Vermont's rich heritage. Surrounded by picturesque scenery, it exudes cultural charm and is a perfect spot for photography and leisurely strolls.
  2. Vermont Museum of Mining and Minerals: Situated 9.7km away, this engaging natural history museum invites families to explore Vermont's geological treasures. With interactive exhibits, it’s an educational experience that highlights the region’s mining history.
  3. Bonnie's Bundles Dolls: Located in Chester, this enchanting attraction showcases a delightful collection of handcrafted dolls. With its romantic atmosphere, it’s an ideal stop for those seeking unique souvenirs or a charming experience.

Things to do recommended for couples

For a romantic getaway in Chester, Vermont, explore Okemo Mountain Resort for skiing and sports vibes, take an adventurous ride on the Solitude Express Ski Lift, or enjoy breathtaking views at Morningside Flight Park. Each offers a unique experience perfect for couples seeking adventure and romance.

Things to do recommended for families

Your family will have a blast at Maple Lanes arcadeAdventureZone, 22.5km from Chester, or enjoy wellness at the Ice House Ice Skating, 20.9km away. For thrill-seekers, the Timber Ripper Mountain Coaster, also 20.9km distant, promises an exhilarating ride!

Things to do recommended for groups

Groups visiting Chester, Vermont, can explore the charming Vermont Country Store for local goods, enjoy a captivating performance at the Weston Playhouse, and unwind with a round of golf at the scenic Fox Run Golf Course, offering a perfect blend of culture, entertainment, and outdoor fun.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to use the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chester with a group: Think about the number of bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Chester with young kids: Travelling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind your distance from family-friendly attractions is a wise choice.
  • Taking your pets with you to Chester: For many, a family getaway isn’t truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Chester: If you’re in search of 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 a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation, making it an ideal destination for Canadian travellers. Whether you’re hitting the slopes or exploring charming local cottages, Chester's welcoming atmosphere caters to all budgets. Nearby regions provide a variety of experiences, from art-filled towns to luxurious retreats, ensuring a memorable vacation filled with the unique charm of this picturesque area. Discover the best of Chester and its enchanting surroundings!

  • Ludlow: Ludlow is a charming city located 17.7km from Chester, renowned for its exceptional ski and adventure offerings. Visitors flock to Ludlow for thrilling winter sports, with access to premier ski resorts and scenic ski fields. The surrounding geography boasts beautiful lakes, majestic mountains, and picturesque valleys, making it an ideal spot for outdoor enthusiasts year-round. In addition to skiing, enjoy hiking and biking in the warmer months, or relax at local eateries that celebrate the region's hospitality.
  • Andover: Andover, a quaint village in the Chester area, is a hidden gem for those seeking adventure and outdoor sports. The village is located conveniently close to Chester and is celebrated for its excellent skiing opportunities. With easy access to ski fields and resorts, Andover is a fantastic base for winter sports lovers. The local landscape showcases stunning lakes, valleys, and mountains, providing ample opportunities for hiking and exploring during the off-season. Experience the charm of a small community while indulging in thrilling activities.
  • Chester Depot: Chester Depot is a delightful neighborhood nestled within Chester, perfect for those looking to immerse themselves in nature and adventure. This area is known for its outdoor experiences, particularly skiing, with easy access to ski resorts and fields. The stunning local features include serene lakes, a nearby national state park, and beautiful beaches for summer enjoyment. Whether you’re skiing in the winter or enjoying hiking, swimming, and picnicking in the warmer months, Chester Depot provides a perfect blend of outdoor activities and relaxation.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 eager to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock substantial 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!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume where you last left off, and manage your travel plans. You can conveniently view your saved or booked properties, which are organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Why people love visiting cozy Chester

The mountains and surrounding scenery provide a peaceful ambiance to your vacation home in Chester. This relaxing city is known for its hiking, skiing and coffeehouses. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Chester

Are you hoping to find top things to see and do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chester a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Stratton Mountain Resort (19.4 mi / 31.2 km)
  • Vermont Country Store (6.4 mi / 10.3 km)
  • Magic Mountain Ski Resort (9.7 mi / 15.6 km)
  • Viking Nordic Center (9.9 mi / 15.9 km)
  • Okemo Mountain Resort (11.4 mi / 18.3 km)
  • Fox Run Golf Course (11.8 mi / 19.1 km)

Exploring the natural features in Chester

Whether you're looking for fun outdoor activities or just want to take in the scenery, Chester is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Lowell Lake State Park (9 mi / 14.5 km)
  • Buttermilk Falls (13.8 mi / 22.1 km)
  • Lake Rescue (14.1 mi / 22.7 km)
  • Mount Ascutney (14.4 mi / 23.1 km)
  • Echo Lake (15.5 mi / 25 km)
  • Amherst Lake (16.4 mi / 26.4 km)

Seasonal weather averages in Chester

Travelers enjoy Chester for its skiing. If you're interested in winter sports, you might consider visiting in January, March, November or February, when snowfall averages 14 inches and temperatures average 25°F.

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 Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a vacation rental?
When considering a vacation rental in Chester, Vermont, the picturesque village centre is an excellent area to stay. This charming locale offers a delightful mix of quaint shops, local eateries, and stunning historic architecture, making it an appealing choice for visitors. The village is also home to the iconic Chester Depot, a beautifully restored train station that reflects the town's rich history and serves as a lovely backdrop for photographs.

Another wonderful option is the nearby area of South Chester, which boasts an array of scenic landscapes and outdoor activities. This region is superb for those who appreciate nature, with access to hiking trails and picturesque views of the Green Mountains. A particularly popular attraction in this area is the beautiful Green Mountain National Forest, where visitors can enjoy a range of outdoor pursuits, from hiking to birdwatching.
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 travelling 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.
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 those seeking ski resort rentals in Chester, Vermont, the nearby Okemo Mountain Resort is the primary destination for winter sports enthusiasts. In Chester, you can find a selection of charming vacation homes and lodges that provide easy access to the slopes, typically only a short drive away. Many properties in this area come equipped with amenities such as spacious living areas, fully equipped kitchens, and cosy fireplaces, ideal for unwinding after a day on the mountain.

In addition to Okemo, the picturesque nearby town of Ludlow offers further accommodation options, featuring ski-in/ski-out properties as well as lodges with convenient shuttle services to the resort. These rentals often provide amenities like hot tubs and game rooms, enhancing the après-ski experience for families or groups. The region is also known for its beautiful rural scenery, with some properties boasting scenic views of the surrounding mountains and forests.
What is the most popular type of vacation rental accomodation in Chester?
In Chester, vacation houses are the most popular type of rental, with about 27 available throughout the area. These properties are typically situated in scenic neighbourhoods, providing a tranquil escape for visitors. Most vacation houses come equipped with fully furnished kitchens, spacious living areas, and outdoor decks or patios, superb for enjoying the picturesque Vermont landscape.
Are there any family house rentals in Chester?
In Chester, Vermont, there are numerous family-friendly house rentals available—specifically around 33 options for visitors to consider. This charming town is located in the picturesque Green Mountains, making it an excellent choice for families seeking both relaxation and outdoor adventure.

Properties in Chester often provide spacious living areas to accommodate families, with many featuring fully equipped kitchens, allowing for easy meal preparation after a day of exploring. Guests can also enjoy amenities like private gardens or patios for outdoor dining and leisure, as well as cozy fireplaces for chilly evenings.
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 or hot tubs, offering a great retreat for relaxation. This charming town, located in the picturesque Green Mountains, provides a serene setting for travellers seeking both comfort and adventure. Many of these rentals come equipped with private pools or hot tubs, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking to unwind after a day of exploring.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chester?
In Chester, Vermont, there are several pet-friendly house rentals available, with around twenty options for travellers to choose from. Many of these properties offer a range of amenities designed for comfort and convenience, including fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The town is situated amidst the picturesque Green Mountains, making it an ideal location for those who enjoy outdoor activities. Nearby, the stunning Okemo Mountain Resort offers opportunities for skiing and snowboarding in winter, while hiking and mountain biking trails are plentiful during the warmer months.
Are there any remote work vacation rentals in Chester?
In Chester, Vermont, there are numerous vacation rentals suitable for remote work, with around 43 options available. Many of these properties come equipped with dedicated workspaces, offering amenities such as desks, comfortable chairs, and high-speed Wi-Fi, ensuring that you can stay productive during your stay.

The charming town is surrounded by picturesque landscapes, making it a serene environment for both work and relaxation. You can expect to find properties with additional features like fully equipped kitchens, spacious living areas, and sometimes outdoor spaces to enjoy nature during breaks. 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 travellers 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, Vermont, popular vacation rental amenities include well-equipped kitchens, which are essential for those who prefer home-cooked meals during their stay. Most rentals also provide cookware, dishware, and utensils, making it easy for guests to prepare and enjoy their meals. Additionally, amenities like refrigerators and microwaves are commonly available, allowing for convenient food storage and quick meal preparation.
When is the best time to visit Chester for a vacation rental?
September is the most popular time to visit Chester, Vermont, as the summer crowds begin to dwindle, allowing for a more relaxed experience. This month offers a delightful blend of warm days and cool evenings, making it ideal for outdoor activities such as hiking and exploring the charming local boutiques. The vibrant fall foliage starts to emerge, providing a stunning backdrop for sightseeing and leisurely strolls through the picturesque town.

The peak season in Chester typically runs from July to September, with July being particularly bustling as families and tourists flock to the area for summer activities. During this time, visitors can enjoy a variety of festivals, outdoor concerts, and scenic drives through the Green Mountains. The comfortable temperatures in the mid-teens to low 20s Celsius are superb for immersing yourself in the beauty of the landscape, whether you are cycling along the trails or enjoying a picnic by the river.

For those seeking a more budget-friendly option, March can be a great time to visit. Although it's considered the low season, you can still enjoy a peaceful retreat while reveling in the beauty of winter in Vermont. This month often features quieter attractions and opportunities for winter sports, such as skiing or snowshoeing in the surrounding areas.
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.
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 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 travellers 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 cosy cabin or a beach house, 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.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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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