Search Vacation Homes in Chester
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 holiday homes
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 HK$1,552
HK$3,205 total
includes taxes & fees
26 Jul - 27 Jul
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 HK$1,764
HK$4,487 total
includes taxes & fees
11 Aug - 12 Aug
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 HK$4,227
HK$7,921 total
includes taxes & fees
27 Jul - 28 Jul
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 HK$1,270
HK$3,136 total
includes taxes & fees
23 Jul - 24 Jul
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.
The price is HK$1,524
HK$3,245 total
includes taxes & fees
21 Jul - 22 Jul
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 HK$1,058
HK$3,864 total
includes taxes & fees
21 Jul - 22 Jul
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 HK$584
HK$2,034 total
includes taxes & fees
21 Jul - 22 Jul
Modern Farm House…minutes to Okemo; 2 King beds!
Modern Farm House…minutes to Okemo; 2 King beds!Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
Rachel L.
The price is HK$1,505
HK$3,933 total
includes taxes & fees
23 Jul - 24 Jul
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 holiday rentals that suit your style
Aparthotels
Private holiday homes
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Latchis Hotel
10/10 Excellent
Find out more about Chester
Chester Vacation Homes information
Number of reviews | 258 |
|---|---|
Accommodation | 910 Vacation Homes |
Lowest Price | HK$2,034 |
Highest Price | HK$8,074 |
Explore a world of travel with Expedia
- Cheap Hotels in Southern Vermont
- Wedding Hotels in Manchester
- B&B in Springfield
- Cabin Rentals in Grafton
- B&B in Putney
- Peru Hotels
- Wedding Hotels in Proctorsville
- Pet-Friendly Hotel Hotels in Jamaica
- Cabin Rentals in Chester
- 3 Star Hotels in Shrewsbury
- 3 Star Hotels in Mount Tabor
- Cottages in Bellows Falls
- Ski Hotel Hotels in Putney
- Hotels near Next Stage Arts
- Apartments in Mount Tabor
- Resorts in Windham
- Dorset Hotels
- Stratton Hotels
- Hotels near Stratton Mountain Resort
- Cabin Rentals in Ludlow
- Guest Houses in Landgrove
- Intrawest Corporation Hotels in Rockingham
- Cottages in Shrewsbury
- Family Hotel Hotels in Manchester
- Ski Hotel Hotels in Weston
- Luxury Hotel Hotels in Southern Vermont
- B&B in Ludlow
- Condo Rentals in Windham County
- B&B in Chester
- Hotels near Magic Mountain Ski Resort
- Hotels near Buttermilk Falls
- Historic Hotel Hotels in Mount Tabor
- Guest Houses in Mount Holly
- Cabin Rentals in Bellows Falls
- Guest Houses in Jamaica
- Resorts in Mount Tabor
- Spa Hotel Hotels in Springfield
- Romantic Hotel Hotels in Chester
- Winhall Hotels
- B&B in Bellows Falls
- Hotels near VINS Nature Center
- Hotels near Sunrise Village Triple Ski Lift
- Cabin Rentals in Putney
- Londonderry Hotels
- Windsor Hotels
- Hotels near Woodstock Country Club
- 5 Star Hotels in Peru
- Hotels near Stratton Mountain Summit Gondola
- Hartland Hotels
- Romantic Hotel Hotels in Manchester
- B&B in Weston
- Manchester Hotels
- Cabin Rentals in Jamaica
- Rockingham Hotels
- Hotels near Fletcher Farm School for the Arts and Crafts
- Resorts in Stratton
- Hotels near Woodstock Town Hall Theatre
- Guest Houses in East Dover
- Motels in Windham
- Putney Hotels
- Pet-Friendly Hotel Hotels in Manchester
- Villas in Cavendish
- Historic Hotel Hotels in Manchester
- Resorts in Bellows Falls
- Hotels near Okemo Mountain Resort
- 5 Star Hotels in Windham
- Resorts in Brownsville
- Motels in Jamaica
- Reading Hotels
- Mount Holly Hotels
- Westminster Hotels
- Mount Tabor Hotels
- Brownsville Hotels
- Pet-Friendly Hotel Hotels in Chester
- Business Hotel Hotels in Manchester Center
- Windham Hotels
- West Townshend Hotels
- Resorts in Cavendish
- Chester Hotels
- Condo Rentals in Ludlow