Chester holiday lettings

We found 1,640 holiday rentals — enter your dates for availability

Discover a selection of 35 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:29 May - 5 Jun

Image gallery for the farmhouse at Big Picture Farm

Snow and ski sports
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

the farmhouse at Big Picture Farm

Townshend

12% off
Price is £10,359
for 7 nights, 1 room
£1,480 per night
includes taxes & fees
the farmhouse at Big Picture Farm

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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. Okemo Mountain Resort and Stratton Mountain Resort are just a couple of the must-see attractions in the area. 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:

  • Okemo Mountain Resort (11.4 mi / 18.3 km)
  • 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)
  • Green Mountain Sugar House (13.3 mi / 21.4 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:

  • Grafton Ponds Outdoor Center (7 mi / 11.2 km)
  • 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)

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

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 those seeking ski resort rentals in Chester, Vermont, the nearby Okemo Mountain Resort is a popular destination, just a short drive away. In Chester itself, visitors can find a variety of charming accommodations, including rustic cabins and quaint cottages that offer a warm retreat after a day on the slopes. Many of these properties come with amenities such as wood-burning fireplaces, fully equipped kitchens, and spacious living areas, making them superb for families or groups.

Additionally, the surrounding areas of Ludlow and Weston provide further options, with rentals often featuring access to ski shuttle services, hot tubs, and outdoor decks for enjoying the picturesque winter scenery. Ludlow, in particular, has a vibrant community atmosphere with local restaurants and shops, adding to the convenience for travellers.

Beyond skiing, the region offers a wealth of activities, including snowshoeing and cross-country skiing in nearby state parks. Many rentals in Chester are also close to beautiful hiking trails and scenic spots, enhancing the overall experience for outdoor enthusiasts.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with around 93 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups. Many holiday houses also come with outdoor decks or patios, superb for enjoying the scenic views of the surrounding countryside.

Additionally, there are about 30 cabins and 18 cottages that provide a more rustic experience, typically located in serene natural settings. These cabins and cottages often include amenities such as fireplaces and outdoor fire pits, enhancing the cosy atmosphere.
Are there any family house rentals in Chester?
In Chester, Vermont, there are numerous family-friendly house rentals available—around 35 to choose from. This charming town is located amidst picturesque landscapes, providing an ideal backdrop for family getaways. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play or families can enjoy a barbecue.

Conveniently located near attractions such as the nearby Okemo Mountain Resort, guests can enjoy a variety of outdoor activities, including hiking, skiing, and snowboarding depending on the season. The local area is also rich in history, with quaint shops and dining options in the town centre that cater to all tastes.
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 come with pools or hot tubs, providing a great option for those looking to relax during their stay. The town is located in a picturesque setting surrounded by the Green Mountains, offering both natural beauty and a charming small-town atmosphere. Many of these rentals feature spacious living areas, well-equipped kitchens, and outdoor spaces where guests can enjoy the serene surroundings.

Travellers can expect amenities such as private pools, hot tubs, and outdoor seating areas, superb for unwinding after a day of exploring the local attractions. Chester also offers close proximity to outdoor activities, including hiking and skiing in the winter months, making it an excellent choice for families or groups seeking a holiday retreat.
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 are several pet-friendly house rentals available, providing an inviting space for travellers with furry companions. The area is known for its picturesque landscapes and charming New England architecture, making it an appealing destination for those looking to enjoy a peaceful retreat. Many of the holiday rentals come equipped with essential amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

Chester's location offers easy access to a variety of outdoor activities, with nearby parks and trails great for walking dogs and exploring the beautiful environment. The surrounding countryside provides opportunities for hiking, biking, and enjoying the natural beauty of Vermont.
Are there any remote work holiday rentals in Chester?
In Chester, Vermont, there are numerous holiday rentals suitable for remote work, with around 147 properties available. This charming town offers a serene environment, great for those looking to blend work and leisure. Many of these rentals are equipped with essential amenities such as free Wi-Fi, which is often available in the rooms, ensuring that you can stay connected during your work hours.

Accommodations range from cozy cabins to spacious homes, many featuring comfortable workspaces, allowing for a productive atmosphere. Additionally, some properties may offer amenities like outdoor areas for relaxation, making it easy to unwind after a day of remote work. The picturesque surroundings provide a great backdrop for those seeking inspiration during their working hours, with access to local parks and scenic views of the Vermont countryside. 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, popular holiday rentals typically feature a range of amenities that cater to the comfort and convenience of travellers. Most properties come equipped with kitchens, allowing guests to prepare their own meals, as well as decks or patios for enjoying the picturesque surroundings. Many rentals also include fireplaces, providing a cosy atmosphere, particularly during the cooler months. Onsite parking is commonly available, making it easier for guests to explore the charming town and its nearby attractions. Additionally, you'll often find coffee and tea makers in these accommodations, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Chester for a holiday rental?
September is the most popular month to visit Chester, Vermont, as it marks the tail end of the peak season that spans from July to September. During this time, outdoor enthusiasts can revel in the stunning autumn foliage, with vibrant hues transforming the landscape into a picturesque scene. The comfortable temperatures, typically ranging from 10 to 20 degrees Celsius, make it an ideal period for hiking the nearby trails or exploring the charming village, known for its quaint shops and local eateries.

July and August are bustling with activity, attracting families and tourists eager to enjoy summer festivals and outdoor adventures. This lively option is superb for those looking to engage in community events and soak up the warm weather while enjoying the natural beauty of the Green Mountains.

For those who prefer a quieter experience, consider visiting in March. Although it falls within the low season, early spring offers a unique opportunity to witness the transition of winter to spring. With fewer crowds, you can enjoy peaceful walks through the snow-dusted scenery, and perhaps even some early-season skiing or snowshoeing.

Regardless of when you decide to visit, Chester has a wealth of experiences to offer, suiting both adventure seekers and those looking for a serene getaway.
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.
What are the top attractions in Chester?
In Chester, Vermont, visitors can explore a variety of charming attractions that reflect the area's rich history and natural beauty. The town centre features the picturesque Green, surrounded by quaint shops and historic buildings, making it a pleasant spot for a leisurely stroll. Nearby, the iconic Chester Depot offers a glimpse into the town's railway history and is a great starting point for exploring the surrounding landscapes.

For outdoor enthusiasts, the nearby Okemo Mountain Resort provides opportunities for hiking, skiing, and enjoying the stunning Vermont scenery. The resort is easily accessible and offers a range of activities throughout the year, suiting both winter sports lovers and summer adventurers.

Additionally, the surrounding countryside is dotted with scenic trails, great for hiking and biking, particularly in the Green Mountain National Forest. The area also hosts a number of seasonal farmers' markets, showcasing local produce and crafts, adding to the community's charm.
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 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 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.
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, 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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