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Chester Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chester vacation rentals

Dining

1. 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 768
AED 1,571 total
includes taxes & fees
17 Aug - 18 Aug
Charming Chester Farmhouse near Near VT Slopes
Exterior

2. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
The price is AED 1,028
AED 2,374 total
includes taxes & fees
20 Aug - 21 Aug
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Exterior

3. 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 3,711 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Vermont Cabin · Mountain Views · Near Okemo
Exterior

4. 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, (170 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 1,349 total
includes taxes & fees
13 Aug - 14 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

5. Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (86 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is AED 268
AED 386 total
includes taxes & fees
13 Aug - 14 Aug
Perfect Getaway! Cozy, Modern & Convenience to Everything!
Exterior

6. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is AED 386
AED 993 total
includes taxes & fees
23 Aug - 24 Aug
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Exterior

7. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is AED 366
AED 877 total
includes taxes & fees
13 Aug - 14 Aug
Cozy Studio Condo with Great Location, WiFi & Kitchenette
TV, DVD player

8. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is AED 197
AED 862 total
includes taxes & fees
25 Aug - 26 Aug
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior

9. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is AED 496
AED 950 total
includes taxes & fees
18 Aug - 19 Aug
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Smart TV, fireplace, books

10. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is AED 767
AED 1,525 total
includes taxes & fees
16 Aug - 17 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
TV, fireplace, foosball, stereo

11. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is AED 564
AED 1,371 total
includes taxes & fees
13 Aug - 14 Aug
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Interior

12. 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, (48 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
The price is AED 694
AED 1,399 total
includes taxes & fees
16 Aug - 17 Aug
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Golf

13. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is AED 366
AED 852 total
includes taxes & fees
18 Aug - 19 Aug
Efficient condo near slopes with kitchenette & great location
TV

14. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is AED 505
AED 1,619 total
includes taxes & fees
9 Sep - 10 Sep
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Interior

15. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is AED 826
AED 2,234 total
includes taxes & fees
13 Aug - 14 Aug
Terrific 3-bedroom cottage with AC in charming Cavendish
Smart TV, fireplace, video games, books

16. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is AED 545
AED 1,874 total
includes taxes & fees
13 Aug - 14 Aug
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Exterior

17. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
Stratton
The price is AED 274
AED 828 total
includes taxes & fees
13 Aug - 14 Aug
Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna
TV, fireplace

18. 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)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is AED 274
AED 1,161 total
includes taxes & fees
13 Aug - 14 Aug
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Children's area

19. Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (17 reviews)
"Nice place "
United States
Janja L.
The price is AED 371
AED 1,259 total
includes taxes & fees
27 Aug - 28 Aug
Cozy Bromley Retreat
Outdoor pool, a heated pool

20. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is AED 1,102
AED 1,999 total
includes taxes & fees
13 Aug - 14 Aug
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
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

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"Very clean nice place"
Michelle 2-night trip
Posted 5 hours ago
Sleep Woodstock Motel

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?

Okemo Mountain Lodging by Vail Resorts: You might like this vacation home rental near Chester. It is in the mountains and offers cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop.

How many vacation rentals will I find in Chester?

Choose from 31 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. Vermont Country Store and Lowell Lake State Park 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.