Chester Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chester holiday rentals

Interior
Whimsical Room & Private Bathroom in Historic Inn

Holiday Home in Chester Depot

Whimsical Room & Private Bathroom in Historic Inn
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is HK$1,003
HK$1,576 total
includes taxes & fees
4 Jan - 5 Jan 2026
Whimsical Room & Private Bathroom in Historic Inn
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"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 HK$1,081
HK$2,604 total
includes taxes & fees
7 Jan - 8 Jan 2026
Chester Farmhouse Ski Retreat near Slopes
Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

Holiday Home in Chester

Cozy Vermont Cabin · Mountain Views · Near Okemo
10.0 out of 10, Exceptional, (3)
"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 HK$4,892
HK$8,640 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Vermont Cabin · Mountain Views · Near Okemo
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is HK$1,050
HK$1,977 total
includes taxes & fees
14 Jan - 15 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
2 bedrooms, desk, free WiFi
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin in Jamaica

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
2.0 star property
10.0 out of 10, Exceptional, (5)
"Great stay"
United States
Chelsea D.
The price is HK$938
HK$1,754 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK
Exterior
Treehouse at Wise Pines- NoBo

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
9.8 out of 10, Exceptional, (14)
"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 HK$1,166
HK$1,454 total
includes taxes & fees
5 Jan - 6 Jan 2026
Treehouse at Wise Pines- NoBo
Private kitchen
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cabin in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (2)
"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 HK$1,155
HK$2,807 total
includes taxes & fees
29 Dec - 30 Dec
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Fridge, microwave, oven, stovetop
Cozy Bromley Retreat

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.8 out of 10, Exceptional, (7)
"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 HK$849
HK$2,716 total
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy Bromley Retreat
Beach
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

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)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is HK$1,568
HK$4,499 total
includes taxes & fees
5 Jan - 6 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is HK$1,936
HK$3,126 total
includes taxes & fees
6 Jan - 7 Jan 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveller
The price is HK$1,516
HK$4,676 total
includes taxes & fees
28 Dec - 29 Dec
Wilmington Retreat Near Trails, Skiing & Festivals
Fridge, microwave, oven, stovetop
Lake Front Family Friendly Escape

Holiday Home in Newport

Lake Front Family Friendly Escape
10.0 out of 10, Exceptional, (4)
"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 HK$917
HK$2,775 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lake Front Family Friendly Escape
Pool
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very good, (78)
"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
The price is HK$2,961
HK$3,680 total
includes taxes & fees
19 Jan - 20 Jan 2026
Long Trail House at Stratton Mountain Resort
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Cabin in Grafton

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (166)
"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 HK$1,322
HK$2,848 total
includes taxes & fees
5 Jan - 6 Jan 2026
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Holiday Home in Newport

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
9.8 out of 10, Exceptional, (18)
"We loved sitting by and listening to the river. Everything was as described."
United States
Jennifer A.
The price is HK$1,555
HK$3,096 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Property grounds
Owl's Nest Treehouse

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (14)
"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 HK$2,138
HK$2,649 total
includes taxes & fees
7 Jan - 8 Jan 2026
Owl's Nest Treehouse
Terrace/patio
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Chalet in Dover

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.8 out of 10, Exceptional, (22)
"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 HK$655
HK$3,121 total
includes taxes & fees
5 Jan - 6 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Chalet in East Dover

Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,076
HK$3,551 total
includes taxes & fees
13 Jan - 14 Jan 2026
Mountain Chalet mins from Mt Snow Skiing/hiking
Iron/ironing board, WiFi, bed sheets
Woodstock Studio | 10 Min to Killington

Apartment in Bridgewater

Woodstock Studio | 10 Min to Killington
10.0 out of 10, Exceptional, (5)
"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 HK$1,159
HK$2,169 total
includes taxes & fees
12 Jan - 13 Jan 2026
Woodstock Studio | 10 Min to Killington
Property grounds
Family Friendly Hilltop House In Putney Vermont

Holiday Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is HK$1,291
HK$2,378 total
includes taxes & fees
5 Jan - 6 Jan 2026
Family Friendly Hilltop House In Putney Vermont
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Staff are exceptionally friendly and helpful "
Brandon 1-night trip
Posted 4 days ago
Pointe at Castle Hill Resort

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 holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Bonnie's Bundles Dolls, or you can select a more secluded option if you're looking for 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 coffee shops and restaurants.

What are some of the best holiday rentals that Chester has to offer?

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing: This holiday home rental outside of Chester is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

How many holiday rentals will I find in Chester?

Choose from 34 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Bonnie's Bundles Dolls and DaVallia Art & Accents are a couple of the family-friendly sights. Stratton Mountain Resort and Vermont Country Store are a couple of places you'll find in the wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals feature extras like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.