Chester Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Chester vacation rentals

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 ￥98,171
￥173,395 total
includes taxes & fees
Mar 8 - Mar 9
Cozy Vermont Cabin · Mountain Views · Near Okemo
Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is ￥36,672
￥71,484 total
includes taxes & fees
Mar 18 - Mar 19
Chester Farmhouse Ski Retreat near Slopes
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "
United States
Samantha R.
The price is ￥43,249
￥52,899 total
includes taxes & fees
Mar 8 - Mar 9
Owl's Nest Treehouse
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, (167 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 ￥26,529
￥56,453 total
includes taxes & fees
Mar 4 - Mar 5
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ￥43,257
￥91,633 total
includes taxes & fees
Mar 4 - Mar 5
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
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 ￥31,936
￥39,392 total
includes taxes & fees
Mar 4 - Mar 5
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

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

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥21,067
￥38,975 total
includes taxes & fees
Mar 18 - Mar 19
Wellness Getaway with a Personal Sauna, and Private River Beach!
Interior

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
Londonderry
9.8 out of 10, Exceptional, (23 reviews)
"Nice house, clean, easy access, well set up for family skiing."
United States
L I.
The price is ￥30,064
￥88,529 total
includes taxes & fees
Mar 4 - Mar 5
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester
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, (21 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 ￥28,309
￥58,871 total
includes taxes & fees
Mar 8 - Mar 9
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Property grounds

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 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 ￥23,591
￥29,589 total
includes taxes & fees
Mar 16 - Mar 17
Treehouse at Wise Pines- NoBo
Interior

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Londonderry
8.8 out of 10, Excellent, (10 reviews)
"We had a wonderful stay."
United States
Joshua
The price is ￥51,663
￥89,126 total
includes taxes & fees
Mar 4 - Mar 5
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Exterior

Insanely romantic treehouse perched next to a stream and rolling hills.

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is ￥62,279
￥138,440 total
includes taxes & fees
Mar 4 - Mar 5
Insanely romantic treehouse perched next to a stream and rolling hills.
Indoor pool

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Okemo Village
10.0 out of 10, Exceptional, (11 reviews)
"Location was perfect for skiing. Hosts were responsive and the stay was pleasant. Would book again."
United States
Paul T.
The price is ￥47,024
￥99,698 total
includes taxes & fees
Apr 1 - Apr 2
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Outdoor spa tub

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is ￥55,594
￥69,102 total
includes taxes & fees
Apr 1 - Apr 2
Long Trail House at Stratton Mountain Resort
Dining

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (35 reviews)
"Great ski-in, ski-out property."
United States
Kristi C.
Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
Interior

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay."
United States
Anonymous traveler
The price is ￥34,971
￥89,420 total
includes taxes & fees
Mar 4 - Mar 5
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Interior

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (14 reviews)
"This was absolutely perfect. Every part of the cabin was well thought out from design to decor. We had such an amazing time and already want to plan another getaway to this place. "
United States
Adam B.
The price is ￥32,712
￥54,598 total
includes taxes & fees
Mar 24 - Mar 25
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥24,691
￥46,677 total
includes taxes & fees
Apr 1 - Apr 2
Family Friendly Hilltop House In Putney Vermont
Smart TV, fireplace

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is ￥66,840
￥135,241 total
includes taxes & fees
Mar 23 - Mar 24
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Smart TV, fireplace, books, computer monitors

6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.

6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
Winhall
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful location close to ski resorts and towns. Well maintained property with all the amenities of home. Had a wonderful time staying here! "
United States
Caroline F.
6 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
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

On The River Inn

On The River Inn

10/10 Excellent
"Friendly and helpful staff "
susan 2-night trip
Posted 2 days ago
On The River Inn

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:

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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. Stratton Mountain Resort and Vermont Country Store are a couple of places you'll find in the larger area.

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.