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Chester Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chester vacation rentals

Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is AED 764
AED 1,547 total
includes taxes & fees
9 Jul - 10 Jul
Charming Chester Farmhouse near Near VT Slopes
Exterior

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is AED 834
AED 2,098 total
includes taxes & fees
29 Jun - 30 Jun
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AED 1,980
AED 3,699 total
includes taxes & fees
9 Jul - 10 Jul
Cozy Vermont Cabin · Mountain Views · Near Okemo
Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (13 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is AED 426
AED 682 total
includes taxes & fees
29 Jun - 30 Jun
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (5 reviews)
"This place can only be described with one word, "WOW". That is the exact thing I said when pulling up to it. The driveway is steep and dirt so it can be intimidating but it isn't that bad at all. We went here on our honeymoon and had to ride 3 hours to get there on a motorcycle. This place was equipped with a beautiful outdoor firepit, 2 gas propane grills, and an indoor propane heater (leave the door cracked). The showers are located at the house on the property and were very clean. There's a...
United States
Ian
The price is AED 347
AED 576 total
includes taxes & fees
29 Jun - 30 Jun
Yurt Oasis in the woods of Hinsdale, NH
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
The price is AED 503
AED 1,577 total
includes taxes & fees
27 Jun - 28 Jun
Hiking Trails On-Site: Cozy Falls Brook Cabin
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
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 254
AED 1,204 total
includes taxes & fees
28 Jun - 29 Jun
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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, (169 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is AED 624
AED 1,333 total
includes taxes & fees
8 Jul - 9 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
The price is AED 562
AED 1,506 total
includes taxes & fees
27 Jun - 28 Jun
Hiking Trails On-site: Cozy Falls Brook Cabin
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, (19 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is AED 592
AED 1,078 total
includes taxes & fees
28 Jun - 29 Jun
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"Great location. Incredible outdoor space and comfortable furnishings."
United States
Debby B.
The price is AED 485
AED 1,669 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
TV, fireplace

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very Good, (35 reviews)
"Appeared dated"
United States
John B.
The price is AED 274
AED 1,165 total
includes taxes & fees
26 Jun - 27 Jun
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Property grounds

Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
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 AED 551
AED 1,650 total
includes taxes & fees
30 Jun - 1 Jul
Lakefront Family Fun Retreat
Interior

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (43 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is AED 625
AED 1,119 total
includes taxes & fees
28 Jun - 29 Jun
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is AED 430
AED 1,622 total
includes taxes & fees
30 Jun - 1 Jul
Chalet Mount Snow/Stratton Skiing/hiking
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
The price is AED 333
AED 1,190 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Bromley Retreat
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is AED 698
AED 1,652 total
includes taxes & fees
14 Jul - 15 Jul
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
House (3 Bedrooms) | Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is AED 540
AED 1,595 total
includes taxes & fees
29 Jun - 30 Jun
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is AED 436
AED 1,643 total
includes taxes & fees
29 Jun - 30 Jun
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."
Lauren 2-night trip
Posted 3 hours ago
Woodstock Inn & Resort

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals in Chester near DaVallia Art & Accents, 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?

Idyllic Lakefront House Suited Two Families: This vacation home rental near Chester is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Chester?

Choose from 30 Expedia vacation rentals in Chester for a memorable vacation.

What’s there to see and do in Chester?

DaVallia Art & Accents and Bonnie's Bundles Dolls are a couple of family-friendly sights. My Minds Design 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.