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Featured Private Vacation Homes in Chester

Estimated price for 1 night/2 adults

Historic & Unique Lodge...minutes To The Winter Fun of Mount Sunapee! ?
Historic & Unique Lodge...minutes To The Winter Fun of Mount Sunapee! ?
23 Spring St, Newport, New Hampshire
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5.0/5 (3 reviews)

Kenneth was extremely informative and helpful with attractions around the area, quick response back to me, etc...

Reviewed on Sep. 7, 2019
Located in the heart of Newport, this historic holiday home is within a 15-minute walk of Newport Golf Club and Newport Historical Society. Perkins Pond and ...
Deluxe 2 Room Queen Suite on the 1st Floor w/ Outdoor Heated Pool
Deluxe 2 Room Queen Suite on the 1st Floor w/ Outdoor Heated Pool
8463 US Route 4, Killington, VT
CA $183
Conveniently located near the ski slopes, this Killington holiday home is within 9 mi (15 km) of Killington Golf Course, Killington Resort and Pico Mountain ...
THE Loft, Stunning Views From a Timber Framed Barn
THE Loft, Stunning Views From a Timber Framed Barn
396 Peterkin Hill Rd, South Woodstock, VT
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5.0/5 (1 reviews)

The loft is one of the coziest, well planned, and well decorated homes that I have stayed in. Dave was such a gracious host! He explained everything and was super helpful. The loft has an amazing view that calms you and helps you experience what Vermont is all about. The loft is new, but the decor ...

Reviewed on Oct. 1, 2019
Situated in South Woodstock, this holiday home is 2.6 mi (4.1 km) from Union Arena Community Center and within 6 miles (10 km) of Woodstock Town Hall Theatre ...
For the 2019-20 Season- Gentle Rental on Pleasant Street
For the 2019-20 Season- Gentle Rental on Pleasant Street
41 Pleasant Street, Ludlow, VT
CA $528
Situated in Ludlow, this holiday home is 0.4 mi (0.7 km) from Dorsey Park and within 3 miles (5 km) of Okemo Mountain Resort and Jackson Gore Ski Resort at Okemo. ...
Large Comfortable House Minutes To Bromley And Stratton Sleeps 10
Large Comfortable House Minutes To Bromley And Stratton Sleeps 10
7 Deer St, Bondville, VT
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4.7/5 (3 reviews)

We rent in the area 2x per year (for the past 5 years) for my family of 5 and my in-law's family of 4. Do date, this has been our favorite home. Plenty of room for everyone, plenty of towels (all thick and white!), very comfortable beds, enough space for everyone to gather and watch tv at night, ...

Reviewed on Feb. 13, 2019
Situated in Bondville, this holiday home is within 9 miles (15 km) of Bromley Mountain Ski Resort, Stratton Mountain Resort and Jamaica State Park. Stratton ...
NEW Listing! Remodeled Victorian-style Duplex With Hiking, Biking, Skiing Nearby
NEW Listing! Remodeled Victorian-style Duplex With Hiking, Biking, Skiing Nearby
516 Route 103, 2nd Floor, Ludlow, VT
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5.0/5 (1 reviews)

Enjoyed our stay, convenient parking, close to downtown

Reviewed on Feb. 20, 2019
Conveniently near to skiing facilities, this Ludlow holiday home is located in the mountains, within 3 miles (5 km) of Dorsey Park and Okemo Mountain Resort, ...
Secluded Get Away Retreat
Secluded Get Away Retreat
429 Hammond Hill Rd, Windsor, VT
CA $429
5.0/5 (23 reviews)

Last house end of a dirt driveway. Quiet, excellent view. Great area. My three dogs, wife and myself loved it. We will definitely will return. Effortless check in and Jennifer was outstanding host.

Reviewed on Aug. 14, 2019
Situated in the mountains, this resort is 2.7 mi (4.3 km) from Mt Ascutney State Park and within 9 miles (15 km) of Old Constitution House and American Precision ...
NEW Listing! Dog-friendly Cabin W/firepit - Ski/golf at Nearby Mountains!
NEW Listing! Dog-friendly Cabin W/firepit - Ski/golf at Nearby Mountains!
825 Stratton Arlington Rd, Stratton, VT
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4.2/5 (5 reviews)

This property was perfect for what we were looking for with a few downfalls. First, the listing pictures show a wood stove in the foyer which is no longer there. It looks like owner recently replaced all the flooring (with the exception of the bathroom which has just ply wood down) and removed the ...

Reviewed on Sep. 3, 2019
Situated in Stratton, this holiday home is within 12 miles (20 km) of Mount Snow, Stratton Mountain Resort and Mount Snow Golf Course. Stratton Mountain Summit ...
[kab-in] A Refined Log Cabin in Woodstock, Vermont
[kab-in] A Refined Log Cabin in Woodstock, Vermont
3369 Hartland Hill Rd, Woodstock, VT
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5.0/5 (8 reviews)

Oh my, what a gem. Beautifully situated, tastefully furnished, immaculately clean. We only stayed for two nights and left wishing we’d stayed longer. We will certainly be back.

Reviewed on Sep. 15, 2019
Situated in Woodstock, this romantic holiday home is within 3 miles (5 km) of Billings Park and Trail, Dana House Museum and Woodstock Town Hall Theatre. Billings ...
Stratton 5-star Home With Ahot Tub! Modern Rustic
Stratton 5-star Home With Ahot Tub! Modern Rustic
2 Bromley Forest Road, Bondville, VT
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5.0/5 (2 reviews)

House was comfortable and well appointed. Would definitely stay again.

Reviewed on Mar. 23, 2019
Situated in Bondville, this historic holiday home is 3.1 mi (5 km) from Bromley Mountain Ski Resort and within 6 miles (10 km) of Gander Gallery and Manchester ...
NEW Listing! Dog-friendly Cabin w/ Fireplace - Close to Skiing/shopping/dining
NEW Listing! Dog-friendly Cabin w/ Fireplace - Close to Skiing/shopping/dining
6 Snowflake Lane, Bondville, VT
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Conveniently located near the ski slopes, this Bondville holiday home is within 6 mi (10 km) of Bromley Mountain Ski Resort, Manchester Designer Outlets and ...
Deluxe Two Queen Bed Standard Hotel Room on 1st Floor w/ Outdoor Heated Pool
Deluxe Two Queen Bed Standard Hotel Room on 1st Floor w/ Outdoor Heated Pool
8463 US Route 4, Killington, VT
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Located near the slopes, this Killington holiday home is in the mountains and within 9 mi (15 km) of Killington Golf Course, Killington Resort and Pico Mountain ...
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Estimated price for 1 night/2 adults

Fullerton Inn

Fullerton Inn

40 The Common, Chester, VT
    2.5 out of 5.0
     
     
    3.8 out of 5 (62 reviews)

    Fullerton InnCA $150

    Nov. 1 - Nov. 2

    Fullerton InnCA $150
    The Karass Inn

    The Karass Inn

    225 Pleasant Street, Chester, VT
      3.0 out of 5.0
       
       
      4.5 out of 5 (49 reviews)

      The Karass InnCA $150

      Oct. 28 - Oct. 29

      The Karass InnCA $150

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