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Cottages, Villas, Apartments in Chester
Holiday Rentals
USA
Vermont (VT)
Cottages, Villas, Apartments in Chester
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Chester
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Internet or Wifi (41)
Washer/Dryer (30)
Air Conditioning (29)
Grill (28)
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Suitability
Kid friendly (37)
Pet friendly (15)
Wheelchair access (0)
Elder access (0)
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Holiday Rental House (38)
Condominium/Apartment (3)
Cabin Holiday Rental (0)
Private Room (0)
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Waterfront (3)
Private Chef (0)
Private Beach (0)
Ski In/Ski Out (0)
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Distance from
5 mi
Stone House Antique Center
Davallia Art & Interiors
The Bargain Corner
Vermont Picker Antiques
Whiting Library
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41 rentals
in Chester.
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!
20
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
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As seen on
King & Queen Suite in Historic Inn Circa 1780
12
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
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Riverfront, family fun, amazing rec room, close to Magic & Okemo
8
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Whimsical Room & Private Bathroom in Historic Inn
7
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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As seen on
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
68
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 5
Match:
Sleeps
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As seen on
Zen of the Woods Tiny Cabin in Okemo Valley
8
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Room in Historic Inn! 20 Minutes to Okemo!
9
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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Honeymoon Suite with Jacuzzi Tub in Historic Inn
6
Holiday Rental House
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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
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1 bedroom
1 bathroom
Sleeps 2
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This tiny house is a 1 bedroom(s), 1 bathrooms, located in Chester, VT.
2
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Vermont Hillside Cottage w/Great View - Pet Friendly
48
Holiday Rental House
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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.
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
10
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Charming Historic Home in Vermont
12
Holiday Rental House
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3 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
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Cheerful residential home with lots of space
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
9
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!
4
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Amazing Vermont Farmhouse, perfect for summer and fall foliage getaways!
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres
2
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Work, Ski, Relax - Big Restored 1860s Farmhouse
1
Holiday Rental House
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7 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
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Spacious retreat with private hot tub, game room, deck, fireplace, & W/D
8
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 13
Match:
Sleeps
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Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Spacious 5-bedroom chalet with AC and WiFi in charming Chester
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
1
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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As seen on
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
FOUR SEASON HOME NEAR OKEMO
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Thistle House at Camp Greenwood Vermont with Sauna
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Sage House at Camp Greenwood Vermont with Sauna
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck
1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches.
3
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
6
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Charming Chester Farmhouse – peaceful and close to everything!
7
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
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As seen on
Cozy farmhouse w/ TV, wifi, w/d, dvd player, kitchen, board games
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
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As seen on
3-bedrooms and bath in welcoming Chester with WiFi, AC.
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Renovated ski house near Okemo and Stratton
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Rustic 150-year-old farmhouse, Jacuzzi included
4
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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Amazing Custom Home on 40+ Acres
10
Holiday Rental House
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6 bedrooms
6 bathrooms
Sleeps 12
Match:
Sleeps
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1
Showing results 1-41 of 41
Frequently Asked Questions about Chester
Do any holiday rentals in Chester have a pool?
Yes, here are some popular holiday rentals in Chester that have a pool:
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!
King & Queen Suite in Historic Inn Circa 1780
Riverfront, family fun, amazing rec room, close to Magic & Okemo
See all holiday rentals with a pool in Chester on Tripadvisor
Do any holiday rentals in Chester have internet access?
Yes, here are some popular holiday rentals in Chester that have internet access:
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!
King & Queen Suite in Historic Inn Circa 1780
Riverfront, family fun, amazing rec room, close to Magic & Okemo
See all holiday rentals in Chester on Tripadvisor
What are the best pet friendly rentals in Chester?
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
See all pet friendly holiday rentals in Chester on Tripadvisor
What are some great rentals in Chester that are kid friendly?
Some of the most popular kid friendly rentals in Chester are:
Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!
King & Queen Suite in Historic Inn Circa 1780
Riverfront, family fun, amazing rec room, close to Magic & Okemo
See all kid friendly holiday rentals in Chester on Tripadvisor
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