Woodstock, Vermont

Vacation Rentals in Woodstock, Vermont

Discover 40 vacation rental properties in Woodstock. From 1 to 7 bedrooms. Average $525/night. 100% have pools.

40 verified listings Book securely on VRBO Prices updated March 2026

40 properties available

Woodstock Village Carriage House

Woodstock Village Carriage House

1 bed 1 bath
PoolA/CWiFiBalcony
$251/night
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Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

2 beds 1 bath
PoolA/CWiFiBalcony
$198/night
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Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

Sunlit VT Country Home w/Hot Tub. Ideal location near Woodstock village

3 beds 2 baths
PoolA/CWiFiBalcony
$302/night
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Delightful Cozy Space in Woodstock Village

Delightful Cozy Space in Woodstock Village

1 bed 1 bath
PoolA/CWiFiBalcony
$226/night
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IT'S FOLIAGE SEASON!

IT'S FOLIAGE SEASON!

1 bed 1 bath
PoolA/CWiFiBalcony
$213/night
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Charming and Chic Vacation Rental

Charming and Chic Vacation Rental

1 bed 1 bath
PoolA/CWiFiBalcony
$235/night
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Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

1 bed 1 bath
PoolA/CWiFiBalcony
$165/night
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Historic Ski Lodge on 112-Acre Vineyard

Historic Ski Lodge on 112-Acre Vineyard

2 beds 1 bath
PoolA/CWiFiBalcony
$196/night
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Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity

Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity

2 beds 1 bath
PoolA/CWiFiBalcony
$409/night
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Greydon Cabin ~ Rustic Luxury in Woodstock VT

Greydon Cabin ~ Rustic Luxury in Woodstock VT

3 beds 2 baths
PoolA/CWiFiBalcony
$530/night
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Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village

Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village

2 beds 2 baths
PoolA/CWiFiBalcony
$296/night
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Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

1 bath
PoolA/CWiFiBalcony
$222/night
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Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

1 bed 1 bath
PoolA/CWiFiBalcony
$165/night
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Vermont Gem Near Woodstock and Quechee

Vermont Gem Near Woodstock and Quechee

3 beds 2 baths
PoolA/CWiFiBalcony
$362/night
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S P R U C E ~ T O P

S P R U C E ~ T O P

4 beds 4 baths
PoolA/CWiFiBalcony
$1,670/night
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PRIVATE & AFFORDABLE charming custom ranch in South Woodstock ! AC and WIFI.

PRIVATE & AFFORDABLE charming custom ranch in South Woodstock ! AC and WIFI.

4 beds 2 baths
PoolA/CWiFiBalcony
$406/night
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NEW! Scenic Ridge - 4bd/3ba cabin in Woodstock, VT

NEW! Scenic Ridge - 4bd/3ba cabin in Woodstock, VT

4 beds 3 baths
PoolA/CWiFiBalcony
$632/night
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Hilltop Homestead : Charming Woodstock Farmhouse, Close to Skiing

Hilltop Homestead : Charming Woodstock Farmhouse, Close to Skiing

3 beds 2 baths
PoolA/CWiFiBalcony
$425/night
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NEW! Woodstock River Front, Sauna & Nature Trails

NEW! Woodstock River Front, Sauna & Nature Trails

3 beds 2 baths
PoolA/CWiFiBalcony
$570/night
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Wise Pines Renovated Barn (Bunkhouse)

Wise Pines Renovated Barn (Bunkhouse)

2 beds 2 baths
PoolA/CWiFiBalcony
$427/night
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Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!

Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!

4 beds 2 baths
PoolA/CWiFiBalcony
$343/night
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Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge

Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge

4 beds 2 baths
PoolA/CWiFiBalcony
$933/night
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NEW Vermont Luxury in Woodstock Village: Private Home, Pond & Mountain Views

NEW Vermont Luxury in Woodstock Village: Private Home, Pond & Mountain Views

3 beds 2 baths
PoolA/CWiFiBalcony
$829/night
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Havenwood, a beautiful private, gated estate in Woodstock, Vermont

Havenwood, a beautiful private, gated estate in Woodstock, Vermont

7 beds 7 baths
PoolA/CWiFiBalcony
$2,762/night
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Charming Retreat in heart of Woodstock, VT

Charming Retreat in heart of Woodstock, VT

4 beds 3 baths
PoolA/CWiFiBalcony
$269/night
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Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"

Perfect Design & Location for the VT Experience. "Hope Upon, Up Above"

4 beds 3 baths
PoolA/CWiFiBalcony
$284/night
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A charming 1820's farmhouse

A charming 1820's farmhouse

5 beds 5 baths
PoolA/CWiFiBalcony
$653/night
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Dog Friendly Home in S. Woodstock

Dog Friendly Home in S. Woodstock

3 beds 3 baths
PoolA/CWiFiBalcony
$362/night
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Relaxing retreat in the mountains 20 min to Killington

Relaxing retreat in the mountains 20 min to Killington

3 beds 1 bath
PoolA/CWiFiBalcony
$279/night
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Perfect Woodstock Getaway! Lovely Riverside Home

Perfect Woodstock Getaway! Lovely Riverside Home

3 beds 2 baths
PoolA/CWiFiBalcony
$342/night
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Dramatic Mountain Ridge house 3 miles from village green

Dramatic Mountain Ridge house 3 miles from village green

3 beds 2 baths
PoolA/CWiFiBalcony
$500/night
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Yellow House on the Hill, 21 Acres, Views, Woodstock Getaway, Dog-friendly

Yellow House on the Hill, 21 Acres, Views, Woodstock Getaway, Dog-friendly

4 beds 2 baths
PoolA/CWiFiBalcony
$751/night
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Historic Home Steps From The Village Green

Historic Home Steps From The Village Green

3 beds 3 baths
PoolA/CWiFiBalcony
$225/night
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Contemporary Townhouse

Contemporary Townhouse

3 beds 3 baths
PoolA/CWiFiBalcony
$225/night
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South Woodstock Village

South Woodstock Village

2 beds 1 bath
PoolA/CWiFiBalcony
$551/night
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Ananda Vue- Lux 3BR/2BA hygge Villa w Fireplace and VIEWS!

Ananda Vue- Lux 3BR/2BA hygge Villa w Fireplace and VIEWS!

3 beds 2 baths
PoolA/CWiFiBalcony
$315/night
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🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺

🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺

4 beds 2 baths
PoolA/CWiFiBalcony
$1,294/night
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Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

6 beds 6 baths
PoolA/CWiFiBalcony
$1,088/night
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Luxury, private, peaceful home with Instagram worthy amenities!

Luxury, private, peaceful home with Instagram worthy amenities!

4 beds 3 baths
PoolA/CWiFiBalcony
$701/night
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Spectacular Views At This Luxury Country Estate, Walking Distance To Town

Spectacular Views At This Luxury Country Estate, Walking Distance To Town

4 beds 2 baths
PoolA/CWiFiBalcony
$396/night
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More destinations in Vermont

Ludlow (398) Killington (396) Stowe (286) Wilmington (219) Warren (200) Dover (172) Stratton (133) Manchester (78) Quechee (78) Winhall (73) West Dover (72) Burlington (66) Jay (61) Colchester (60) Cambridge (50) Waitsfield (50) Peru (45) Mendon (44) Castleton (39) Manchester Center (37)