Chester Vacation Rentals
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50 rentals in Chester.
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Vermont Hillside Cottage w/Great View - Pet Friendly
2 bedrooms
1 bathroom
Sleeps 6
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Stay at Our Completely Restored 1799 Barn in Chester, Vermont
1 bedroom
2 bathrooms
Sleeps 10
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
5 bedrooms
4 bathrooms
Sleeps 8
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Hugging Bear Inn RENT ENTIRE INN
6 bedrooms
7 bathrooms
Sleeps 18
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Amare Guesthouse, renovated in-town victorian
3 bedrooms
2 bathrooms
Sleeps 6
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Beautifully renovated circa 1900 Farmhouse on 31 magnificient acres.
3 bedrooms
4 bathrooms
Sleeps 6
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Charming Fully Renovated One-Room Schoolhouse on 22+ acres
2 bedrooms
1 bathroom
Sleeps 10
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Wide Open Mountain and Valley Views, Beautiful Sunsets, Scenic Southern Vermont
3 bedrooms
3 bathrooms
Sleeps 7
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Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!
3 bedrooms
2 bathrooms
Sleeps 10
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Resort Home with Pool * 'The Castle Hill' Spa & Tennis
3 bedrooms
3 bathrooms
Sleeps 6
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All-Seasons Home on 500 Acres w/ Private Lake for Fishing/Canoeing, Near Skiing!
8 bedrooms
4 bathrooms
Sleeps 20
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Home Sweet Grafton Home
3 bedrooms
2 bathrooms
Sleeps 6
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Stay Safe! Stay strong!
3 bedrooms
2 bathrooms
Sleeps 6
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Secluded, rustic home w/ private hot tub & huge deck - 5 miles to Okemo
3 bedrooms
4 bathrooms
Sleeps 8
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Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend
7 bedrooms
3 bathrooms
Sleeps 12
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Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!
5 bedrooms
3 bathrooms
Sleeps 12
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Okemo. SNOWMAGEDDON! THIS WEEKEND & NEXT OPEN! 2BR , Fireplace/laundry/shuttle
2 bedrooms
1 bathroom
Sleeps 7
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Poetic Mountaintop Log Cabin nestled in the woods
3 bedrooms
2 bathrooms
Sleeps 6
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Tranquil family home set in a quiet neighborhood and easy access to outdoor fun
4 bedrooms
2 bathrooms
Sleeps 10
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3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley.
3 bedrooms
1 bathroom
Sleeps 7
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Beautiful Okemo chalet with Hot Tub
4 bedrooms
3 bathrooms
Sleeps 16
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Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain
3 bedrooms
2 bathrooms
Sleeps 8
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Secluded, dog-friendly home w/ foosball table, game system - near Black River
2 bedrooms
2 bathrooms
Sleeps 8
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Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo
8 bedrooms
4 bathrooms
Sleeps 20
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6 Bedroom House Located near Magic , Stratton and Okemo Mountain
6 bedrooms
3 bathrooms
Sleeps 16
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Beautiful Vermont Retreat House near Okemo Mountain
4 bedrooms
2 bathrooms
Sleeps 6
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Quiet Hills of Andover Vermont. Enjoy a gorgeous view from the deck!
3 bedrooms
2 bathrooms
Sleeps 8
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Renovated 1920s ski condo, walk to dining, on bus route to slopes!
3 bedrooms
1 bathroom
Sleeps 5
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Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!
3 bedrooms
2 bathrooms
Sleeps 10
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Chester Farmhouse on 100 Acres, 15 Min to Okemo!
5 bedrooms
2 bathrooms
Sleeps 12
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo
5 bedrooms
3 bathrooms
Sleeps 12
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Okemo VT Mansion - Sleep 17 Chef Optional
6 bedrooms
10 bathrooms
Sleeps 17
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Tranquil family home set in a quiet neighborhood and easy access to outdoor fun
4 bedrooms
2 bathrooms
Sleeps 10
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Secluded, rustic home w/ private hot tub & huge deck - 5 miles to Okemo
3 bedrooms
4 bathrooms
Sleeps 8
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Historic Chester House 10-30 Mins to 5 Mountains!
5 bedrooms
2 bathrooms
Sleeps 7
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Renovated 1920s ski condo, walk to dining, on bus route to slopes!
3 bedrooms
1 bathroom
Sleeps 5
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8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun
8 bedrooms
4 bathrooms
Sleeps 20
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Charming & spacious two-story townhome w/balcony and shared pool-close to Okemo
3 bedrooms
4 bathrooms
Sleeps 8
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Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!
4 bedrooms
3 bathrooms
Sleeps 9
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Deluxe mountain hideaway w/ a game room, deck, & amazing views - close to skiing
3 bedrooms
3 bathrooms
Sleeps 12
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Private Chester Home w/ Deck, Mins to Skiing!
3 bedrooms
3 bathrooms
Sleeps 8
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Tentrr Signature Site - Ahsahka
1 bedroom
1 bathroom
Sleeps 4
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*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern
4 bedrooms
2 bathrooms
Sleeps 10
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Secluded, dog-friendly home w/ foosball table, game system - near Black River
2 bedrooms
2 bathrooms
Sleeps 8
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Vermont charm 8 minutes to Okemo Mountain!
2 bedrooms
1 bathroom
Sleeps 5
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Elegant victorian with free wifi, private washer/dryer - Near Okemo
5 bedrooms
3 bathrooms
Sleeps 12
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo
5 bedrooms
3 bathrooms
Sleeps 12
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Secluded log cabin on 25 acres bordering state forest with trails nearby
3 bedrooms
2 bathrooms
Sleeps 10
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New listing! Very accommodating home on 170+ acres w/ multiple living spaces
6 bedrooms
4 bathrooms
Sleeps 16
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NEW! Secluded Cabin w/ Fire Pit, 8 Mi to Okemo Mtn
3 bedrooms
2 bathrooms
Sleeps 6
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