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Chester Vacation Rentals

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50 rentals in Chester.
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Vermont Hillside Cottage w/Great View - Pet Friendly, vacation rental in Chester

Vermont Hillside Cottage w/Great View - Pet Friendly

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stay at Our Completely Restored 1799 Barn in Chester, Vermont, vacation rental in Chester

Stay at Our Completely Restored 1799 Barn in Chester, Vermont

1 bedroom
2 bathrooms
Sleeps 10
Match: Sleeps
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax, vacation rental in Chester

Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Hugging Bear Inn RENT ENTIRE INN, vacation rental in Chester

Hugging Bear Inn RENT ENTIRE INN

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Amare Guesthouse, renovated in-town victorian, vacation rental in Chester

Amare Guesthouse, renovated in-town victorian

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautifully renovated circa 1900 Farmhouse on 31 magnificient acres., vacation rental in Chester

Beautifully renovated circa 1900 Farmhouse on 31 magnificient acres.

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming Fully Renovated One-Room Schoolhouse on 22+ acres, vacation rental in Chester

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Wide Open Mountain and Valley Views, Beautiful Sunsets, Scenic Southern Vermont, vacation rental in Chester

Wide Open Mountain and Valley Views, Beautiful Sunsets, Scenic Southern Vermont

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!, vacation rental in Chester

Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Resort Home with Pool * 'The Castle Hill'  Spa & Tennis, vacation rental in Chester

Resort Home with Pool * 'The Castle Hill' Spa & Tennis

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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All-Seasons Home on 500 Acres w/ Private Lake for Fishing/Canoeing, Near Skiing!, vacation rental in Chester

All-Seasons Home on 500 Acres w/ Private Lake for Fishing/Canoeing, Near Skiing!

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Home Sweet Grafton Home, vacation rental in Chester

Home Sweet Grafton Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stay Safe! Stay strong!, vacation rental in Chester

Stay Safe! Stay strong!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded, rustic home w/ private hot tub & huge deck - 5 miles to Okemo, vacation rental in Chester

Secluded, rustic home w/ private hot tub & huge deck - 5 miles to Okemo

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend, vacation rental in Chester

Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend

7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!, vacation rental in Chester

Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Okemo. SNOWMAGEDDON! THIS WEEKEND & NEXT OPEN!  2BR , Fireplace/laundry/shuttle, vacation rental in Chester

Okemo. SNOWMAGEDDON! THIS WEEKEND & NEXT OPEN! 2BR , Fireplace/laundry/shuttle

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Poetic Mountaintop Log Cabin nestled in the woods, vacation rental in Chester

Poetic Mountaintop Log Cabin nestled in the woods

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil family home set in a quiet neighborhood and easy access to outdoor fun, vacation rental in Chester

Tranquil family home set in a quiet neighborhood and easy access to outdoor fun

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley., vacation rental in Chester

3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley.

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beautiful Okemo chalet with Hot Tub, vacation rental in Chester

Beautiful Okemo chalet with Hot Tub

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain, vacation rental in Chester

Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded, dog-friendly home w/ foosball table, game system - near Black River, vacation rental in Chester

Secluded, dog-friendly home w/ foosball table, game system - near Black River

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo, vacation rental in Chester

Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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6 Bedroom House Located near Magic , Stratton and Okemo Mountain, vacation rental in Chester

6 Bedroom House Located near Magic , Stratton and Okemo Mountain

6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful Vermont Retreat House near Okemo Mountain, vacation rental in Chester

Beautiful Vermont Retreat House near Okemo Mountain

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Hills of Andover Vermont. Enjoy a gorgeous view from the deck!, vacation rental in Chester

Quiet Hills of Andover Vermont. Enjoy a gorgeous view from the deck!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Renovated 1920s ski condo, walk to dining, on bus route to slopes!, vacation rental in Chester

Renovated 1920s ski condo, walk to dining, on bus route to slopes!

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!, vacation rental in Chester

Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Chester Farmhouse on 100 Acres, 15 Min to Okemo!, vacation rental in Chester

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, vacation rental in Chester

Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Okemo VT Mansion - Sleep 17 Chef Optional, vacation rental in Chester

Okemo VT Mansion - Sleep 17 Chef Optional

6 bedrooms
10 bathrooms
Sleeps 17
Match: Sleeps
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Tranquil family home set in a quiet neighborhood and easy access to outdoor fun, vacation rental in Chester

Tranquil family home set in a quiet neighborhood and easy access to outdoor fun

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded, rustic home w/ private hot tub & huge deck - 5 miles to Okemo, vacation rental in Chester

Secluded, rustic home w/ private hot tub & huge deck - 5 miles to Okemo

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Historic Chester House 10-30 Mins to 5 Mountains!, vacation rental in Chester

Historic Chester House 10-30 Mins to 5 Mountains!

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Renovated 1920s ski condo, walk to dining, on bus route to slopes!, vacation rental in Chester

Renovated 1920s ski condo, walk to dining, on bus route to slopes!

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun, vacation rental in Chester

8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun

8 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Charming & spacious two-story townhome w/balcony and shared pool-close to Okemo, vacation rental in Chester

Charming & spacious two-story townhome w/balcony and shared pool-close to Okemo

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!, vacation rental in Chester

Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Deluxe mountain hideaway w/ a game room, deck, & amazing views - close to skiing, vacation rental in Chester

Deluxe mountain hideaway w/ a game room, deck, & amazing views - close to skiing

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Private Chester Home w/ Deck, Mins to Skiing!, vacation rental in Chester

Private Chester Home w/ Deck, Mins to Skiing!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Ahsahka, vacation rental in Chester

Tentrr Signature Site - Ahsahka

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern, vacation rental in Chester

*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded, dog-friendly home w/ foosball table, game system - near Black River, vacation rental in Chester

Secluded, dog-friendly home w/ foosball table, game system - near Black River

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vermont charm 8 minutes to Okemo Mountain!, vacation rental in Chester

Vermont charm 8 minutes to Okemo Mountain!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Elegant victorian with free wifi, private washer/dryer - Near Okemo, vacation rental in Chester

Elegant victorian with free wifi, private washer/dryer - Near Okemo

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, vacation rental in Chester

Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Secluded log cabin on 25 acres bordering state forest with trails nearby, vacation rental in Chester

Secluded log cabin on 25 acres bordering state forest with trails nearby

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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New listing! Very accommodating home on 170+ acres w/ multiple living spaces, vacation rental in Chester

New listing! Very accommodating home on 170+ acres w/ multiple living spaces

6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Secluded Cabin w/ Fire Pit, 8 Mi to Okemo Mtn, vacation rental in Chester

NEW! Secluded Cabin w/ Fire Pit, 8 Mi to Okemo Mtn

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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