Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Chester vacation rentals

Exterior

Vacation Home in Chester

Cozy Vermont Cabin · Mountain Views · Near Okemo
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
$968 nightly
The price is $1,084
Jan 25 - Jan 26
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
Fridge, microwave, oven, stovetop

Chalet in Chester

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
10.0 out of 10, Exceptional, (10 reviews)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
$501 nightly
The price is $561
Jan 20 - Jan 21
Total with taxes and fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Dining

Vacation Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17 reviews)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$321 nightly
The price is $360
Jan 20 - Jan 21
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Outdoor spa tub

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (78 reviews)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
$433 nightly
The price is $489
Jan 20 - Jan 21
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
Exterior

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"The folks are SUPER and made me feel very welome"
United States
Mark
$227 nightly
The price is $254
Jan 26 - Jan 27
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior

Chalet in Plymouth

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
$594 nightly
The price is $665
Feb 9 - Feb 10
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Private kitchen

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$235 nightly
The price is $263
Jan 20 - Jan 21
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Exterior

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (16 reviews)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
$315 nightly
The price is $342
Jan 20 - Jan 21
Total with taxes and fees
Owl's Nest Treehouse
Property grounds

Cottage in Jamaica

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was great and the hosts very communicative and checking in to make sure we were all set. We will be hopefully making this a yearly trip as we loved the seclusion and beautiful area. "
United States
Kyle M.
$223 nightly
The price is $252
Jan 28 - Jan 29
Total with taxes and fees
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Interior

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$272 nightly
The price is $296
Jan 20 - Jan 21
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior detail

Vacation Home in Dorset

Charming Dorset Cottage Retreat.
2.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay at this beautiful, cozy cottage in Dorset. It’s close to multiple ski mountains and the charming town of Manchester, and the hosts were super friendly and helpful. Check-in and check-out were easy, and the place was just as advertised."
United States
Sarah S.
$711 nightly
The price is $796
Jan 26 - Jan 27
Total with taxes and fees
Charming Dorset Cottage Retreat.
TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Jan 20 - Jan 21
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Beach

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (46 reviews)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$270 nightly
The price is $305
Feb 3 - Feb 4
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior

Cabin in Grafton

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (166 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$326 nightly
The price is $365
Jan 20 - Jan 21
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

Cabin in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
$321 nightly
The price is $362
Jan 20 - Jan 21
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Fridge, microwave, oven, stovetop

Chalet in Dover

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
10.0 out of 10, Exceptional, (6 reviews)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
United States
Chris I.
$520 nightly
The price is $588
Jan 20 - Jan 21
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Terrace/patio

Vacation Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
$537 nightly
The price is $583
Jan 21 - Jan 22
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Fridge, microwave, oven, stovetop

Vacation Home in Dover

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
10.0 out of 10, Exceptional, (10 reviews)
"Nice in all respects,"
United States
Ken
$1,286 nightly
The price is $1,453
Jan 20 - Jan 21
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Lobby

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (33 reviews)
"Very nice accommodations and location!"
United States
Michael M.
$317 nightly
The price is $358
Feb 1 - Feb 2
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (14 reviews)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
$172 nightly
The price is $188
Jan 20 - Jan 21
Total with taxes and fees
Treehouse at Wise Pines- NoBo
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $274 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals in Chester near Bonnie's Bundles Dolls, or you can select a more remote option if you want a relaxing stay. The ski slopes and shops are just a few reasons why tourists like Chester. While you're in the area, grab a bite or have a drink at the coffeehouses and restaurants.

What are some of the best vacation rentals in Chester?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This vacation home rental near Chester is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chester?

Choose from 35 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of family-friendly sights. While in the area, you can also visit popular places like Okemo Mountain Resort and Stratton Mountain Resort.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.