Chester Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chester holiday rentals

Dining
Chester Farmhouse Ski Retreat near Slopes

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 HK$1,083
HK$2,610 total
includes taxes & fees
19 Jan - 20 Jan
Chester Farmhouse Ski Retreat near Slopes
Exterior
Cozy Vermont Cabin · Mountain Views · Near Okemo

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 HK$4,904
HK$8,766 total
includes taxes & fees
12 Jan - 13 Jan
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!

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 HK$1,052
HK$1,938 total
includes taxes & fees
19 Jan - 20 Jan
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!

The Studio with a View. Bring your dog, too!
2.0 star property
Brattleboro
10.0 out of 10, Exceptional, (1 review)
"The perfect and cozy crash pad for a weekend ski trip! The Studio made us forget about the 9 degree weather outside and had all we needed. Would recommend to anyone looking for a relaxing Vermont getaway and would stay again in a heartbeat!"
United States
Michael A.
The price is HK$779
HK$1,790 total
includes taxes & fees
12 Jan - 13 Jan
The Studio with a View. Bring your dog, too!
Property grounds
Treehouse at Wise Pines- NoBo

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 HK$1,169
HK$1,466 total
includes taxes & fees
12 Jan - 13 Jan
Treehouse at Wise Pines- NoBo
Interior
Beautiful country cabin with hot tub and outdoor shower in Londonderry

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 HK$1,158
HK$2,849 total
includes taxes & fees
13 Jan - 14 Jan
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Children’s area
Cozy Bromley Retreat

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 HK$707
HK$2,534 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Bromley Retreat
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

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 HK$1,403
HK$2,901 total
includes taxes & fees
12 Jan - 13 Jan
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Property grounds
Lake Front Family Friendly Escape

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 HK$935
HK$2,842 total
includes taxes & fees
26 Jan - 27 Jan
Lake Front Family Friendly Escape
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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 HK$1,325
HK$2,837 total
includes taxes & fees
12 Jan - 13 Jan
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow 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 HK$730
HK$3,166 total
includes taxes & fees
12 Jan - 13 Jan
Mountain Chalet mins from Mt Snow Skiing/hiking
Interior
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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 HK$1,933
HK$3,134 total
includes taxes & fees
13 Jan - 14 Jan
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Outdoor spa tub
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
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
The price is HK$2,968
HK$3,689 total
includes taxes & fees
12 Jan - 13 Jan
Long Trail House at Stratton Mountain Resort
Exterior
Owl's Nest Treehouse

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 HK$2,144
HK$2,622 total
includes taxes & fees
12 Jan - 13 Jan
Owl's Nest Treehouse
Lobby
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.8 out of 10, Excellent, (32 reviews)
"Very nice accommodations and location!"
United States
Michael M.
The price is HK$826
HK$2,980 total
includes taxes & fees
1 Feb - 2 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Outdoor pool, a heated pool
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.2 out of 10, Wonderful, (18 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is HK$345
HK$2,293 total
includes taxes & fees
3 Feb - 4 Feb
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds
Vermont Suite | 10 Min to Woodstock & Killington

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 HK$912
HK$1,876 total
includes taxes & fees
14 Jan - 15 Jan
Vermont Suite | 10 Min to Woodstock & Killington
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

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 HK$1,863
HK$2,284 total
includes taxes & fees
25 Jan - 26 Jan
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is HK$1,364
HK$2,453 total
includes taxes & fees
12 Jan - 13 Jan
Family Friendly Hilltop House In Putney Vermont
Exterior
Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.4 out of 10, Exceptional, (3 reviews)
"We had a great stay. Place was very romantic with great views. Host was responsive."
United States
Brian G.
The price is HK$1,466
HK$5,048 total
includes taxes & fees
12 Jan - 13 Jan
Romantic Riverbed Treehouse - hot tub & new sauna!
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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"This place is a must stay, I’ll come back every year. So Beautiful. "
Max 1-night trip
Posted 1 day ago
The Shire Woodstock

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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chester?

Choose from 35 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. While in the area, you can also visit popular places such as Okemo Mountain Resort and Stratton Mountain Resort.

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.