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

Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
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.
The price is ￥25,194
￥56,966 total
includes taxes & fees
Jan 20 - Jan 21
Chester Farmhouse Ski Retreat near Slopes
Fridge, microwave, oven, stovetop

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

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
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.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
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.
The price is ￥99,681
￥176,062 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Vermont Cabin · Mountain Views · Near Okemo
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2 reviews)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is ￥21,391
￥40,462 total
includes taxes & fees
Jan 20 - Jan 21
Wellness Getaway with a Personal Sauna, and Private River Beach!
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
2.0 star property
Brattleboro
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.
The price is ￥19,806
￥41,704 total
includes taxes & fees
Jan 19 - Jan 20
The Studio with a View. Bring your dog, too!
Interior

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
10.0 out of 10, Exceptional, (2 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
The price is ￥23,530
￥57,746 total
includes taxes & fees
Jan 19 - Jan 20
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Property grounds

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
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
The price is ￥23,768
￥29,811 total
includes taxes & fees
Jan 19 - Jan 20
Treehouse at Wise Pines- NoBo
Property grounds

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
2.0 star property
Jamaica
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.
The price is ￥21,568
￥39,963 total
includes taxes & fees
Jan 28 - Jan 29
Cottage-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Property grounds

Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo
Woodstock
9.8 out of 10, Exceptional, (25 reviews)
"Friendly owners with a very comfortable and accommodating space.Very well thought out with a great common space .Hiking trails , fire pit , animals , fresh eggs and produce in season.Highly recommended!!"
United States
Jo-Alice S.
The price is ￥23,768
￥29,811 total
includes taxes & fees
Jan 19 - Jan 20
Treehouse at Wise Pines- SoBo
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (19 reviews)
"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"
United States
Kimberly R.
The price is ￥28,521
￥59,141 total
includes taxes & fees
Jan 18 - Jan 19
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.4 out of 10, Exceptional, (10 reviews)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
The price is ￥17,136
￥54,974 total
includes taxes & fees
Jan 21 - Jan 22
Cozy Bromley Retreat
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥23,056
￥75,432 total
includes taxes & fees
Jan 27 - Jan 28
Chalet Mount Snow/Stratton Skiing/hiking
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
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
The price is ￥26,937
￥57,854 total
includes taxes & fees
Jan 19 - Jan 20
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Property grounds

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is ￥18,396
￥56,922 total
includes taxes & fees
Jan 26 - Jan 27
Lake Front Family Friendly Escape
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
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
The price is ￥43,574
￥53,640 total
includes taxes & fees
Feb 8 - Feb 9
Owl's Nest Treehouse
Interior

Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
9.4 out of 10, Exceptional, (3 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is ￥22,104
￥43,780 total
includes taxes & fees
Jan 19 - Jan 20
Cozy cabin in charming Londonderry
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥34,241
￥41,794 total
includes taxes & fees
Jan 20 - Jan 21
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is ￥29,662
￥51,316 total
includes taxes & fees
Jan 20 - Jan 21
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is ￥17,746
￥37,088 total
includes taxes & fees
Jan 19 - Jan 20
Vermont Suite | 10 Min to Woodstock & Killington
Smart TV, fireplace, Netflix, streaming services

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22 reviews)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is ￥25,156
￥79,455 total
includes taxes & fees
Feb 10 - Feb 11
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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

The Manchester View

The Manchester View

10/10 Excellent
"Excellent "
Rebecca 2-night trip
Posted 1 day ago
The Manchester View

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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.