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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 House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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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Beautifully Renovated 1850’s Victorian Home In The Village Of Chester

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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HISTORIC, SPACIOUS + PEACEFUL VICTORIAN FARMHOUSE- PERFECT FALL GETAWAY!!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT AUTUMN ESCAPE-20 MIN TO OKEMO!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely stone home and outdoor space to breath. Fall 2020 extended stay welcome.

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Hugging Bear Inn RENT ENTIRE INN

Private Room
6 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Work, Hike, Ski, Relax - Big Restored 1860s Farmhouse

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Quiet country cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Grafton Village Haven

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Wide Open Mountain and Valley Views, Beautiful Sunsets, Scenic Southern Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Okemo Mountain Chalet W/ Hot Tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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The Stoma Ranch Outdoor Hot tub

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Log home perfect for a family getaway - 5 miles to Okemo Mtn Resort!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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'Everything VT' Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Resort Home with Pool * 'The Castle Hill' Spa & Tennis

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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Secluded log cabin on 25 acres bordering state forest with trails nearby

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Post and Beam with beautiful Okemo View-Plan a Spring Golf Get Away Weekend

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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*NEWLY RENOVATED* Road-trippers Oasis - 3min walk to Grafton Inn & Tavern

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Poetic Mountaintop Log Cabin nestled in the woods

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5-Bedroom Winter Wonderland with 3 fireplaces

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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NEW LISTING! Charming & spacious, two-story townhome - close to Okemo!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Summer sale going on now! 3000+ sq ft home great for family! Sanitized & cleaned

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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3+ Bedrooms 2+flrs of living space (1400 sq ft) near Magic, Stratton & Bromley.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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The Hideaway Chalet. 3bed + sleeping loft on 10 acres. Dog friendly

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Beautiful Okemo chalet with Hot Tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Cozy & Bright Log Cabin just 8 minutes from Okemo Mountain

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Farmhouse with great views of Okemo.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Victorian recently updated with free WiFi/ deck/ fireplace - Near Okemo

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Vermont 1828 Reunion House, sleeps 16 5 miles to Okemo

Holiday Rental House
8 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Vermont Country Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The most beautiful and iconic home in VT---230 acres of pure bliss

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
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Renovated 1920s ski condo, walk to dining, on bus route to slopes!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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New listing! Very accommodating home on 170+ acres w/ multiple living spaces

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Historic Chester House 10-30 Mins to 5 Mountains!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Family Fun House with a private tube

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Village Ski Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Modern Farmhouse minutes to Skiing & Golf

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Vermont charm 8 minutes to Okemo Mountain!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Farmhouse on the Connecticut River

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Southern Vermont Contemporary Ski Mountain Home At Its Best

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Corona? My Sharona! Enjoy the Ski Season Safely In Your Own Home Away From Home!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Family Fun House

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Cute VT Bungalow With 180 Degree View of NH

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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1820 House

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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