Chester holiday rentals

We found 1,617 holiday rentals — enter your dates for availability
Discover a selection of 31 homes, 11 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:18 Dec - 25 Dec

Dining
Property grounds
Interior
Living area
Exceptional
(48 reviews)

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

Ludlow

8% off
AU$8,607
for 7 nights, 1 chalet
AU$1,230 per night
includes taxes & fees
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails
Welcome to the Blue Moon Bungalow!
Fully stocked kitchen with plenty of room to prepare a family dinner
The first floors open plan is great for large groups.
Deer Room - 1st floor bedroom with a queen bed.
Exceptional
(11 reviews)

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

Chester

8% off
AU$4,940
for 7 nights, 1 chalet
AU$706 per night
includes taxes & fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Private kitchen
Living area
Property grounds
Pool
Exceptional
(16 reviews)

Cozy Ski-House by Okemo Hot Tub & Mountain Privacy

Cavendish

8% off
AU$16,398
for 7 nights, 1 cabin
AU$2,343 per night
includes taxes & fees
Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
Sports court
Exterior
Interior
Private kitchen
Exceptional
(82 reviews)

Beautiful Lakeview Log Cabin on 60-Acre Property

Peru

8% off
AU$35,135
for 7 nights, 1 home
AU$5,019 per night
includes taxes & fees
Beautiful Lakeview Log Cabin on 60-Acre Property
Room
living room with fireplace and gorgeous custom details
pond is river fed and very clear water
Property grounds
Exceptional
(125 reviews)

Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!

Bridgewater Corners

12% off
AU$11,076
for 7 nights, 1 home
AU$1,582 per night
includes taxes & fees
Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!
Front door
Living area
Back porch
View from mudroom
Exceptional
(40 reviews)

Wishing Well Cabin

Jamaica

8% off
AU$3,752
for 7 nights, 1 cabin
AU$536 per night
includes taxes & fees
Wishing Well Cabin
Primary bedroom balcony
Interior
Sitting room looking into the kitchen.
Private kitchen
Exceptional
(8 reviews)

Views of Stratton, Minutes from the Slopes, EV Charging Level 2

Bondville

8% off
AU$15,598
for 7 nights, 1 home
AU$2,228 per night
includes taxes & fees
Views of Stratton, Minutes from the Slopes, EV Charging Level 2
Kitchen (main level)
Master bedroom looking Southwest (upper level
Den area main level (baby not included!)
Winter looking Southeast
Exceptional
(25 reviews)

All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!

Mount Holly

8% off
AU$5,780
for 7 nights, 1 cabin
AU$826 per night
includes taxes & fees
All Season Three Level Log Vacation Home On 21 Acres Between Okemo & Killington!
Exterior
Living area
Interior
Private kitchen
Exceptional
(16 reviews)

Okemo Mountain View Retreat

Cavendish

8% off
AU$10,120
for 7 nights, 1 home
AU$1,446 per night
includes taxes & fees
Okemo Mountain View Retreat
Antique Cabin
Porch -Summer
Antique Cabin
Exterior
Exceptional
(89 reviews)

Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton

Jamaica

8% off
AU$5,962
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
Interior
Pool
lots of room to relax in front of fireplace
Views from one of several decks in the unit
Exceptional
(56 reviews)

Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section

Killington

8% off
AU$11,350
for 7 nights, 1 home
AU$1,621 per night
includes taxes & fees
Multi-Level Slopeside Townhouse End Unit in Sunrise's Timberline Section
Living area
Interior
Exterior
Interior
Exceptional
(105 reviews)

Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub

Killington

8% off
AU$10,438
for 7 nights, 1 home
AU$1,491 per night
includes taxes & fees
Luxury Ski House on Killington Mtn, 2 beds & Den w/ 3 en-suite baths, hot tub
Living area
Exterior
Private kitchen
Terrace/patio
Wonderful
(5 reviews)

Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit

Ludlow

6% off
AU$12,733
for 7 nights, 1 home
AU$1,819 per night
includes taxes & fees
Stunning VT Lakefront and Ski House - Hottub, Fast Wifi, A/C, & Firepit
Coffee options galore!
IMG 1540
Main dining space with seating for 12
Outdoor dining
Exceptional
(7 reviews)

Stylish new A Frame with Lake Rescue dock access

Ludlow

8% off
AU$7,799
for 7 nights, 1 home
AU$1,114 per night
includes taxes & fees
Stylish new A Frame with Lake Rescue dock access
Private kitchen
Small views of all 3 living room spaces and wet bar
Interior
Exterior
Exceptional
(67 reviews)

Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail

Bridgewater Corners

13% off
AU$18,684
for 7 nights, 1 home
AU$2,669 per night
includes taxes & fees
Artisan Ski House for Groups! Killington + Okemo in Minutes. Walk to Long Trail
Covered outdoor patio with views of the lake, connecting to king bedroom
Front of home (late fall sunset)
The Great Room and dining table - seats 10
View (summer) from the covered / screened-in outdoor patio
Exceptional
(20 reviews)

5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C

Ludlow

8% off
AU$15,381
for 7 nights, 1 home
AU$2,197 per night
includes taxes & fees
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A/C
Private kitchen
Interior
Bar (on property)
Room
Exceptional
(79 reviews)

Western Mountain Lodge on River and Close to Stratton

Jamaica

17% off
AU$24,301
for 7 nights, 1 home
AU$3,472 per night
includes taxes & fees
Western Mountain Lodge on River and Close to Stratton
Interior
Pool
.
Outdoor dining
Exceptional
(35 reviews)

Reading Farms Estate

Reading

8% off
AU$40,307
for 7 nights, 1 home
AU$5,758 per night
includes taxes & fees
Reading Farms Estate
Bedroom 3 - queen bed
Image from trailhead
Living Room - looking out over mountains
Lower Level Bar/Kitchenette
Exceptional
(67 reviews)

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington

8% off
AU$14,633
for 7 nights, 1 home
AU$2,090 per night
includes taxes & fees
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
House from Outside
Living room and dining area with views of Ascutney Mountain
Kitchen with soapstone counters, cherry wood floors, and walk-in food closet.
Second master with ensuite bathroom
Exceptional
(42 reviews)

Exquisite Log Home with views near Woodstock, Vermont

Brownsville

15% off
AU$4,395
for 7 nights, 1 home
AU$628 per night
includes taxes & fees
Exquisite Log Home with views near Woodstock, Vermont
Private driveway with ramp to enter house. Gently babbling stream in the front
Front of house, early spring
Light filled kitchen
Bedroom #2 Queen bed with large windows & french doors
Exceptional
(7 reviews)

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Weston

8% off
AU$5,844
for 7 nights, 1 home
AU$835 per night
includes taxes & fees
Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Front of house in winter
Chef's Kitchen
Yoga Studio
Front of House - Summer
Exceptional
(60 reviews)

Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!

Plymouth

14% off
AU$15,013
for 7 nights, 1 home
AU$2,145 per night
includes taxes & fees
Historic 1840's Home with large deck, outdoor living room & fire pit. Sleeps 19!
Living room w/TV Cable, game table, games, local magazines, & electric fireplace
Interior
front porch with Adirondack chairs and a snowboard bench and icicle lights
2nd floor bathroom w/washer drier, 2 showers, extra linens, shampoo and soap
Exceptional
(60 reviews)

Victorian Village Home in Town! with access to shuttle service to Okemo.

Ludlow

12% off
AU$9,928
for 7 nights, 1 home
AU$1,418 per night
includes taxes & fees
Victorian Village Home in Town! with access to shuttle service to Okemo.
Living area
Pool in the nearby recreational building
Living area
Room
Exceptional
(140 reviews)

Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace

Ludlow

8% off
AU$18,474
for 7 nights, 1 apartment
AU$2,639 per night
includes taxes & fees
Mountain Paradise—SKI-ON/SKI-OFF Okemo Ski Getaway ⛷ hot tubs, pool, fireplace

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • Connecticut River State Park (9.5 mi / 15.2 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

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.
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 Stayz.
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.
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.
Are all fees included in the Chester holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chester holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Chester holiday homes?
You can find great discounts on holiday homes in Chester on Stayz, 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.
Can I change or cancel my Chester holiday home booking on Stayz?
To find Chester holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chester?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Chester holiday home?
Book your Chester holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chester?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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