Chester holiday lettings

We found 1,575 holiday rentals — enter your dates for availability

Discover a selection of 33 homes, 10 cabins and other holiday rentals in Chester that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as a fireplace and garden. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chester

Showing deals for:23 Jan - 30 Jan

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

8% off
Price is £3,493
for 7 nights, 1 chalet
£499 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

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Why visit Chester

  • Outdoor pursuits: Chester is perfect for skiing and adventure sports, set in picturesque countryside.
  • Charming local towns: Explore nearby historical towns known for their friendly locals and quaint vibes.
  • Varied accommodation options: Choose from private homes, cosy condos, and charming cabins for your stay.
  • Stunning national parks: Discover beautiful parks and scenic mountains for hiking and relaxation.
  • Family-friendly activities: Enjoy a range of attractions suitable for visitors of all ages.

Popular types of accommodation in Chester

If you're considering a getaway to Chester, you'll find a variety of delightful accommodation options to suit your needs. The most popular types of vacation rentals include houses, cosy condos, and charming cabins. Whether you're seeking private rentals in Chester or spacious house rentals, we have an array of available rentals to ensure you enjoy a memorable stay in this historic city.

  • Houses: The most sought-after option for holidaymakers in Chester, offering spacious and comfortable living for families and groups.
  • Condos: A popular choice, these self-contained units provide modern amenities and convenient access to local attractions.
  • Cabins: Ideal for a rustic getaway, these charming retreats often feature beautiful natural surroundings.
  • Apartments: A practical option for solo travellers or couples, providing a homely atmosphere in the heart of Chester.
  • Cottages: Quaint and cosy, these delightful spaces offer a true taste of country living.**

Top attractions in and around Chester

Chester, Vermont, is ideal for skiing and adventure sports, offering a variety of attractions for those seeking outdoor pursuits, cultural experiences, and family-friendly activities. The area boasts stunning national parks, scenic mountains, and lovely parks, making it a perfect destination for travellers looking to explore the great outdoors and enjoy a memorable holiday.

  • Lowell Lake State Park: Nestled 5.6km from Chester, this park offers stunning scenery and outdoor adventures, perfect for hiking, picnicking, and birdwatching amidst tranquil natural surroundings.
  • DaVallia Art & Accents: Located in the heart of Chester, this gallery showcases local art and crafts, providing a cultural experience that highlights the talents of regional artists in a charming setting.
  • Vermont Museum of Mining and Minerals: Situated 3.7km away, this family-friendly museum features fascinating exhibits on Vermont's mining history, making it an engaging stop for all ages.

Things to do recommended for couples

Chester, Vermont, offers delightful couple experiences. Enjoy skiing at Okemo Mountain Resort, only 6.8km away, or embark on an adventurous scenic flight at Morningside Flight Park, 7.5km from town. For a thrilling day, take the Sachem Ski Lift, also 7.5km away, and embrace the winter wonderland.

Things to do recommended for families

Families visiting Chester, Vermont, can have a fantastic time at Maple Lanes arcadeAdventureZone, just 8.7km away, enjoy ice skating at The Ice House recreationCentre, 8.1km away, and experience thrills on the Timber Ripper Mountain Coaster, also 8.1km from Chester.

Things to do recommended for groups

Groups visiting Chester, Vermont, can enjoy a trip to the Vermont Country Store, located 3.7km away, or catch a show at the Weston Playhouse, 6.2km distant. Don't miss the West River Farmers Market, 6.8km from Chester, for a taste of local culture and produce.

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

When travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your key preferences. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chester with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many others on Vrbo.
  • Traveling to Chester with young kids: Embarking on a journey with young children can present its own set of challenges. It’s essential to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Chester: For many families, a holiday wouldn't feel complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations 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 in search of holiday rentals offering discounts for stays of a month or more, you've come to the perfect destination. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or even a private pool to your criteria.

Where to stay near Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation for visitors. Nestled amidst the picturesque Cheshire countryside and rolling hills, it’s perfect for skiing and outdoor sports. Just a stone's throw away, explore charming nearby towns with their historical vibes and friendly locals. Whether you prefer the tranquillity of budget accommodation or the luxury of city centre lodgings, Chester promises an unforgettable holiday experience.

  • Ludlow: Situated 6.8km from Chester, Ludlow is a charming city renowned for its winter sports and outdoor adventures. The area attracts visitors for its exceptional skiing opportunities, with several ski fields and resorts nearby, making it a popular destination for thrill-seekers and sports enthusiasts alike. The scenic beauty of the surrounding landscape, including picturesque lakes, towering mountains, and serene valleys, adds to the allure. Whether you're carving down the slopes or enjoying a leisurely stroll by the lake, Ludlow offers a delightful experience for all adventurers.
  • Springfield: Just 3.7km from Chester, Springfield is another gem for those who love skiing and outdoor activities. This city is well-known for its access to ski resorts and fields that cater to all skill levels. The nearby national state park provides an excellent backdrop for hiking and exploration, ensuring that nature lovers have plenty to discover. With its beautiful lakes and mountainous terrain, Springfield offers a perfect blend of adventure and relaxation, making it a fantastic choice for a day trip.
  • Grafton: Located a mere 3.7km from Chester, Grafton is a quaint city that beckons outdoor enthusiasts and ski lovers. The area is celebrated for its ski fields and resorts, providing ample opportunities for winter sports. Surrounded by breathtaking valleys and mountains, Grafton serves as a gateway to splendid landscapes that are ideal for hiking and other outdoor pursuits. Visitors can enjoy the tranquil lakes and immerse themselves in the natural beauty that Grafton has to offer, ensuring a memorable experience for those seeking adventure in the great outdoors.

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 on your upcoming journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you may enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated space for you to craft new journeys, refine your plans, or manage your bookings with ease. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting cosy Chester

The mountains and surrounding scenery provide a peaceful ambience to your holiday home in Chester. This relaxing city is known for its hiking, skiing and coffee shops. 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 searching for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Chester a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Jamaica State Park (13.4 mi / 21.6 km)

Exploring the natural features in Chester

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Chester. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Winhall River (14.8 mi / 23.7 km)
  • Echo Lake (15.5 mi / 25 km)

Seasonal weather averages in Chester

Travellers 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 35 cm and temperatures average -4°C.

Travelling to and around Chester

Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying 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 holiday rental?
When looking for the best area to stay in Chester, Vermont, for a holiday rental, the village centre is an excellent choice. This charming area is characterised by its picturesque New England architecture and a warm, welcoming atmosphere. Staying here places you within walking distance of delightful local shops and eateries, allowing you to easily immerse yourself in the local culture.

One of the top attractions in the village is the historic Chester Town Hall, which hosts various events throughout the year and adds to the charming character of the area. Additionally, the nearby Vermont Institute of Contemporary Arts offers a unique cultural experience with rotating exhibitions that showcase the works of both local and national artists.
How much does it cost to rent a holiday home in Chester?
Prices for holiday 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 holiday 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 renting ski resort accommodations near Chester, Vermont, travellers should consider the nearby Okemo Mountain Resort, which is just a short drive away. In the village of Ludlow, you'll find a variety of rental options, including charming chalets and modern condos that cater to ski enthusiasts. Many of these properties come equipped with amenities such as heated pools, hot tubs, and ski storage, ensuring a comfortable stay after a day on the slopes.

In Chester itself, visitors can explore quaint historic homes and cosy cabins, often featuring rustic decor and modern conveniences like fully equipped kitchens and wood-burning stoves. The town's picturesque setting provides a serene atmosphere, with easy access to nearby hiking trails for those looking to enjoy winter walks or summer hikes.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of rental, with around 27 available throughout the area. These properties typically provide a comfortable and spacious environment, featuring multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or larger groups exploring the picturesque surroundings. Additionally, there are approximately 10 cabins, which offer a rustic charm and often include amenities such as fireplaces and outdoor spaces for enjoying the natural beauty of the region. Several cottages and chalets can also be found, providing a quaint and cosy atmosphere for those seeking a more intimate stay.
Are there any family house rentals in Chester?
In Chester, Vermont, there are numerous family-friendly house rentals available, with around 33 options to choose from. The area is known for its charming New England ambiance and proximity to outdoor activities, making it an excellent choice for families. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.
Can I rent a holiday home with a pool or hot tub in Chester?
In Chester, Vermont, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for those seeking relaxation and leisure. This charming town, located in the picturesque Green Mountains, offers a variety of rental options that cater to families and groups. Many properties come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the serene surroundings.
Can I find long-stay holiday rentals in Chester?
A long-stay holiday 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 is a variety of pet-friendly house rentals available, with around 20 options for travellers seeking accommodation that welcomes their furry companions. The town offers a charming New England atmosphere, with many holiday rentals situated in scenic locations, often featuring amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces like patios or gardens, ideal for enjoying the fresh air with pets.
Are there any remote work holiday rentals in Chester?
In Chester, Vermont, remote work holiday rentals are quite abundant, with around 43 options available for those looking to blend work and leisure. Many of these properties come equipped with dedicated office spaces, including desks and comfortable desk chairs, ensuring a productive environment. High-speed Wi-Fi is commonly provided, along with amenities such as computer monitors and laptop workspaces, making it easy for travellers to stay connected while enjoying the beautiful surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
September is the most popular time to visit Chester, Vermont, as the summer crowds begin to wane, allowing for a more tranquil experience in this picturesque town. The peak season spans from July to September, attracting outdoor enthusiasts and families seeking to immerse themselves in the vibrant autumn foliage and charming local festivals.

During September, visitors can enjoy pleasant weather with daytime temperatures reaching the low 20s Celsius, great for hiking, biking, and exploring the local shops and cafes. The stunning landscapes of the Green Mountains provide a breathtaking backdrop for outdoor activities, and the nearby Okemo Mountain Resort offers excellent opportunities for fall hiking.

For those looking for a more budget-friendly option, consider visiting in March. This month, while quieter, still offers great experiences such as late-season skiing at nearby resorts and the chance to witness the beauty of a snow-covered landscape without the crowds.
How early should I book a Chester holiday rental?
Book your Chester holiday 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 holiday 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 holiday 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chester holiday 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.

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