Chester Vacation Rentals
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Bathrooms
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5 mi
27 rentals in Chester.
Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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King & Queen Suite in Historic Inn Circa 1780
Rental Home
1 bedroom
1 bathroom
Sleeps 6
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Riverfront, family fun, amazing rec room, close to Magic & Okemo
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Whimsical Room & Private Bathroom in Historic Inn
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Rental Home
1 bedroom
1 bathroom
Sleeps 5
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Zen of the Woods family-friendly tiny cabin sleeps 4, minutes to Okemo!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Room in Historic Inn! 20 Minutes to Okemo!
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Honeymoon Suite with Jacuzzi Tub in Historic Inn
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vermont Hillside Cottage w/Great View - Pet Friendly
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquility awaits for your stay at our cherished log home on 6 secluded acres.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Vermont historic home
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Stunning farmhouse in gorgeous historic village
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cheerful residential home with lots of space
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing, Spacious, Family Friendly Getaway
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Private Chester Home w/ Deck, Mins to Skiing!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW Renovated historic Vermont Farmhouse, close to skiing & hiking
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Farmhouse with mountain views close to Ski Resorts
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Work, Ski, Relax - Big Restored 1860s Farmhouse
Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
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Spacious retreat with private hot tub, game room, deck, fireplace, & W/D
Rental Home
5 bedrooms
3 bathrooms
Sleeps 13
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Amazing Custom Home on 40+ Acres
Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
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Showing results 1-27 of 27
Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
- King & Queen Suite in Historic Inn Circa 1780
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
- King & Queen Suite in Historic Inn Circa 1780
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- The best pet friendly rentals in Chester are:
- This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
- This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
- Vermont Hillside Cottage w/Great View - Pet Friendly
- Some of the most popular kid friendly rentals in Chester are:
- Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
- King & Queen Suite in Historic Inn Circa 1780
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
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