Chester Vacation Rentals
Chester Vacation Rentals
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26 rentals in Chester.
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Vermont Hillside Cottage w/Great View - Pet Friendly
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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
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SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Log cabin on 25 acres bordering state forest with trails nearby.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
Rental Home
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cheerful residential home with lots of space
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Amazing Custom Home on 40+ Acres
Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
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Luxury stone farmhouse - lots of room! Perfect for Spring/Summer getaway.
Rental Home
7 bedrooms
3 bathrooms
Sleeps 16
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NEW! Modern Chester Escape < 20 Mi to Bromley Mtn!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Charming Farmhouse in Chester
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hugging Bear Inn RENT ENTIRE INN
Private Room
6 bedrooms
7 bathrooms
Sleeps 18
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Historic Chester House 10-30 Mins to 5 Mountains!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegantly Appointed Ski Home in Charming Village of Chester, VT
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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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Work, Ski, Relax - Big Restored 1860s Farmhouse
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Ski Okemo - Spacious, Family Friendly Chalet
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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Spacious 1-level ranch, mtn. views, htd. flrs , fire pit, 10 mi. to Okemo!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Spacious historic home close to village green
Rental Home
4 bedrooms
2 bathrooms
Sleeps 11
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Historic Home in Vermont
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
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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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Picturesque VT Farmhouse on 12 Acres, near 4 major ski areas and VSF Horse Show
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
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Showing results 1-26 of 26
Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- Hugging Bear Inn RENT ENTIRE INN
- Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
- Amazing Custom Home on 40+ Acres
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Hugging Bear Inn RENT ENTIRE INN
- Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
- Amazing Custom Home on 40+ Acres
- Some of the most popular kid friendly rentals in Chester are:
- Hugging Bear Inn RENT ENTIRE INN
- Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
- Amazing Custom Home on 40+ Acres