Chester Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chester vacation homes
1. Charming Chester Farmhouse near Near VT Slopes
Charming Chester Farmhouse near Near VT SlopesChester 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."
Stephanie F.
The price is CA $277
CA $569 total
includes taxes & fees
Aug 12 - Aug 13
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 AndoverAndover
10.0 out of 10, Exceptional, (1 review)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
Lorraine C.
The price is CA $392
CA $905 total
includes taxes & fees
Aug 4 - Aug 5
3. Cozy Vermont Cabin · Mountain Views · Near Okemo
Cozy Vermont Cabin · Mountain Views · Near OkemoChester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
pauline
The price is CA $755
CA $1,415 total
includes taxes & fees
Aug 8 - Aug 9
4. Okemo's Back Room - in the heart of the village on the shuttle route!
Okemo's Back Room - in the heart of the village on the shuttle route!Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
jonathan w.
The price is CA $227
CA $560 total
includes taxes & fees
Aug 3 - Aug 4
5. 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 GoreMt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
Cheri V.
The price is CA $221
CA $718 total
includes taxes & fees
Aug 2 - Aug 3
6. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski ShuttleLudlow
9.8 out of 10, Exceptional, (113 reviews)
"Clean great cozy place!"
Himanshu P.
7. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to LiftsStratton
The price is CA $104
CA $360 total
includes taxes & fees
Aug 12 - Aug 13
8. Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Bear`s Den in Ludlow, Okemo Views + Epic Game RoomLudlow
The price is CA $253
CA $566 total
includes taxes & fees
Aug 3 - Aug 4
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.
Find vacation rentals that suit your style
Cabins
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Keene Elm City Hotel, an Ascend Collection Hotel
8/10 Good
Find out more about Chester
Chester Vacation Homes information
Number of reviews | 274 |
|---|---|
Accommodation | 1006 Vacation Homes |
Lowest Price | CA $360 |
Highest Price | CA $1,415 |
Explore a world of travel with Expedia
- Woodstock Hotels
- Motels in Ludlow
- Hotels near Buttermilk Falls
- Bellows Falls Hotels
- Condo Rentals in Stratton
- Cozy Family Chalet with Mountain Views – 15 Mins to Okemo & Ludlow
- Stone Hearth Inn and Eatery
- Luxury Hotels in Ludlow
- Bromley View Inn
- Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
- Hotels near Magic Mountain Ski Resort
- Hotel Wedding Venues Hotels in Jamaica
- Winhall Hotels
- Cruise Ships in Woodstock
- Inns in Hartford
- B&B in Mount Tabor
- Hilltop 9
- Cabin Rentals in West Dover
- Cabin Rentals in Peru
- Okemo Ski Condo
- Chester Hotels
- 3 Star Hotels in Jamaica
- Brownsville Hotels
- Adults Only Resorts & in Mountain Acres
- Hotels near Bromley Mountain Ski Resort
- Inns in Cavendish
- Cottages in Shrewsbury
- Private wing of the Largest Colonial Revival Mansion in the US
- Bondville Hotels
- Golden Stage Inn B&B
- Killington Hotels
- Villas in Bondville
- Hotels near Weston Priory
- Rockingham Hotels
- Townhomes in Cavendish
- Cabin Rentals in Putney
- Grafton Hotels
- Wyndham Hotels in Bellows Falls
- Cabin Rentals in Londonderry
- Villas in Killington
- Pinnacle Lodge
- Apartments in Stratton
- Hotels with smoking rooms in Bellows Falls
- Mountainside 3
- Hotels near Stratton Mountain Resort
- Springfield Hotels
- East Jamaica Hotels
- Londonderry Hotels
- Condo Rentals in Killington
- Ascutney Hotels
- Lgbt Friendly Hotels in Ludlow
- Fireplace
- Cabin Rentals in Mount Holly
- Best Western Hotels in Cavendish
- Cabin Rentals in Marlboro
- B&B in West River Trail
- Resorts in Stratton
- Cabin Rentals in Killington
- Resorts in Reading
- Motels in White River Junction
- Cabin Rentals in Mount Snow Valley
- Resorts in Brownsville
- Sun Lodge
- Hotels near Okemo Mountain Resort
- Treehouses in Woodstock
- Apartments in Killington
- Chester Depot Hotels
- Fat Sheep Farm & Cabins
- Jamaica Hotels
- Cabin Rentals in Ludlow
- Motels in Bridgewater
- Windsor Hotels
- Cabin Rentals in Central Vermont
- Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
- Ludlow Hotels
- The Hartness House
- The Overlook House
- Reillys Rest
- Windham Hotels