Holiday Rentals in Chester
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28 rentals in Chester.
Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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King & Queen Suite in Historic Inn Circa 1780
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
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Riverfront, family fun, amazing rec room, close to Magic & Okemo
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Whimsical Room & Private Bathroom in Historic Inn
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Zen of the Woods family-friendly tiny cabin sleeps 4, minutes to Okemo!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Room in Historic Inn! 20 Minutes to Okemo!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Honeymoon Suite with Jacuzzi Tub in Historic Inn
Holiday Rental House
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
Holiday Rental House
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.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Vermont historic home
Holiday Rental House
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
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning farmhouse in gorgeous historic village
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cheerful residential home with lots of space
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing, Spacious, Family Friendly Getaway
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Chester Home w/ Deck, Mins to Skiing!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW Renovated historic Vermont Farmhouse, close to skiing & hiking
Holiday Rental House
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
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Farmhouse with mountain views close to Ski Resorts
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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SPACIOUS VICTORIAN FARMHOUSE- 20 MIN TO OKEMO
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Work, Ski, Relax - Big Restored 1860s Farmhouse
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spacious retreat with private hot tub, game room, deck, fireplace, & W/D
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Rate Reduced Luxury stone farmhouse - lots of room! Perfect for Summer getaway.
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Custom Home on 40+ Acres
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-28 of 28
Frequently Asked Questions about Chester
- Yes, here are some popular holiday rentals in Chester that have a pool:
- Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
- Yes, here are some popular holiday rentals in Chester that have internet access:
- Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
- 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!
- Riverfront, family fun, amazing rec room, close to Magic & Okemo
- Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
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