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Holiday Homes in Chester

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

Vermont Hillside Cottage w/Great View - Pet Friendly

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax, holiday 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, holiday rental in Chester

Hugging Bear Inn RENT ENTIRE INN

6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Charming Fully Renovated One-Room Schoolhouse on 22+ acres, holiday 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, holiday 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!, holiday 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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OKEMO SKI HOUSE W/ NEW 6 PERSON HOT TUB, 6 Bedrooms  (2 K, 3 Q, 1 f/t), holiday rental in Chester

OKEMO SKI HOUSE W/ NEW 6 PERSON HOT TUB, 6 Bedrooms (2 K, 3 Q, 1 f/t)

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming Ski Chalet Minutes From Okemo Mountain!, holiday rental in Chester

Charming Ski Chalet Minutes From Okemo Mountain!

5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Snowbird Lane - South Hill Ludlow - Well Appointed House, holiday rental in Chester

Snowbird Lane - South Hill Ludlow - Well Appointed House

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming & Affordable Home with Spectacular Mtn Views!!, holiday rental in Chester

Charming & Affordable Home with Spectacular Mtn Views!!

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

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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8 Bedroom Home - 500 Acres w/Private Lake near Great Skiing - for All-Season Fun, holiday 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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Slopeside 2BR 2BTH Condo at Magic Mountain, holiday rental in Chester

Slopeside 2BR 2BTH Condo at Magic Mountain

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stay Safe! Stay strong!, holiday rental in Chester

Stay Safe! Stay strong!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend, holiday 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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Tranquil family home set in a quiet neighborhood and easy access to outdoor fun, holiday 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, holiday 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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Home Sweet Grafton Home, holiday rental in Chester

Home Sweet Grafton Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ski, Snowboard, Hike, or just Relax at our Spacious Home for Family and Friends!, holiday 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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Slopeside Condominium In The Heart Of Southern Vermont, holiday rental in Chester

Slopeside Condominium In The Heart Of Southern Vermont

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!, holiday rental in Chester

Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Vermont Ski Chalet - Fireplace, Walk to Mountain, Great for Groups, holiday rental in Chester

Vermont Ski Chalet - Fireplace, Walk to Mountain, Great for Groups

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley., holiday 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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Riverside family-friendly condo w/pool-close to skiing & hiking, holiday rental in Chester

Riverside family-friendly condo w/pool-close to skiing & hiking

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Deluxe mountain hideaway w/ a game room, deck, & amazing views - close to skiing, holiday rental in Chester

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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Secluded, dog-friendly home w/ foosball table, game system - near Black River, holiday 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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Comfortable, dog-friendly ski condo w/ shared seasonal pool, on shuttle route!, holiday rental in Chester

Comfortable, dog-friendly ski condo w/ shared seasonal pool, on shuttle route!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Okemo chalet with Hot Tub, holiday 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, holiday 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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Isolated Rural Inn & Cottages! Private Water, Generator, Wifi! Scenic Weston Inn, holiday rental in Chester

Isolated Rural Inn & Cottages! Private Water, Generator, Wifi! Scenic Weston Inn

10 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Private Ludlow Village Home - 2 Miles from Okemo Base W/Access To Okemo Shuttle, holiday rental in Chester

Private Ludlow Village Home - 2 Miles from Okemo Base W/Access To Okemo Shuttle

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo, holiday 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, holiday 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, holiday rental in Chester

Beautiful Vermont Retreat House near Okemo Mountain

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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6Bed/4Ba Spacious Ski House Central Location on Okemo Shuttle-Sleeps 14, holiday rental in Chester

6Bed/4Ba Spacious Ski House Central Location on Okemo Shuttle-Sleeps 14

6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo, holiday 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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Renovated 1920s ski condo, walk to dining, on bus route to slopes!, holiday 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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Chester Farmhouse on 100 Acres, 15 Min to Okemo!, holiday rental in Chester

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Historic Chester House 10-30 Mins to 5 Mountains!, holiday rental in Chester

Historic Chester House 10-30 Mins to 5 Mountains!

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ludlow Home - Under 3 Miles to Okemo Mtn Resort!, holiday rental in Chester

Ludlow Home - Under 3 Miles to Okemo Mtn Resort!

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Chester Home w/ Views ~10 Mi to Okemo Mtn Resort!, holiday 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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Isolated Rural Inn! Private Water, Generator, 3000MG Wifi, Scenic Weston Inn Nea, holiday rental in Chester

Isolated Rural Inn! Private Water, Generator, 3000MG Wifi, Scenic Weston Inn Nea

7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Private Chester Home w/ Deck, Mins to Skiing!, holiday rental in Chester

Private Chester Home w/ Deck, Mins to Skiing!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern, holiday 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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Reboot & Relax while surrounded by Vermont beauty., holiday rental in Chester

Reboot & Relax while surrounded by Vermont beauty.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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4 Bedroom 100 Yr Old Bungalow, holiday rental in Chester

4 Bedroom 100 Yr Old Bungalow

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ski house / mountain bike, holiday rental in Chester

Ski house / mountain bike

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Vermont charm 8 minutes to Okemo Mountain!, holiday 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, holiday 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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Secluded log cabin on 25 acres bordering state forest with trails nearby, holiday 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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