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Woodstock Vacation Rentals

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Bedrooms

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5 mi
41 rentals in Woodstock.
Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock
Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock
Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock

Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Design & Location for the VT Experience. "Hope Upon, Up Above", vacation rental in Woodstock
Perfect Design & Location for the VT Experience. "Hope Upon, Up Above", vacation rental in Woodstock
Perfect Design & Location for the VT Experience. "Hope Upon, Up Above", vacation rental in Woodstock

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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PRIVATE & AFFORDABLE charming custom ranch  in South Woodstock !  AC and WIFI., vacation rental in Woodstock
PRIVATE & AFFORDABLE charming custom ranch  in South Woodstock !  AC and WIFI., vacation rental in Woodstock
PRIVATE & AFFORDABLE charming custom ranch  in South Woodstock !  AC and WIFI., vacation rental in Woodstock

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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IT'S FOLIAGE SEASON!, vacation rental in Woodstock
IT'S FOLIAGE SEASON!, vacation rental in Woodstock
IT'S FOLIAGE SEASON!, vacation rental in Woodstock

IT'S FOLIAGE SEASON!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy 1850s home on the riverfront with mountain & river views - dog-friendly, vacation rental in Woodstock
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly, vacation rental in Woodstock
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly, vacation rental in Woodstock

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Woodstock Village Carriage House, vacation rental in Woodstock
Woodstock Village Carriage House, vacation rental in Woodstock
Woodstock Village Carriage House, vacation rental in Woodstock

Woodstock Village Carriage House

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Scenic South Woodstock, Vermont home, vacation rental in Woodstock
Scenic South Woodstock, Vermont home, vacation rental in Woodstock
Scenic South Woodstock, Vermont home, vacation rental in Woodstock

Scenic South Woodstock, Vermont home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vermont Gem Near Woodstock and Quechee, vacation rental in Woodstock
Vermont Gem Near Woodstock and Quechee, vacation rental in Woodstock
Vermont Gem Near Woodstock and Quechee, vacation rental in Woodstock

Vermont Gem Near Woodstock and Quechee

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity, vacation rental in Woodstock
Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity, vacation rental in Woodstock
Carriage House - 250 Private Acres; Views, Gardens, Skiing, Farm, Serenity, vacation rental in Woodstock

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock
Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock
Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock

Lovely All Season Treehouse at Wise Pines, 5 minutes from downtown Woodstock, VT

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski, vacation rental in Woodstock
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski, vacation rental in Woodstock
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski, vacation rental in Woodstock

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

Rental Home
6 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Delightful Cozy Space in Woodstock Village, vacation rental in Woodstock
Delightful Cozy Space in Woodstock Village, vacation rental in Woodstock
Delightful Cozy Space in Woodstock Village, vacation rental in Woodstock

Delightful Cozy Space in Woodstock Village

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Idyllic Woodstock, VT Cottage, vacation rental in Woodstock
Idyllic Woodstock, VT Cottage, vacation rental in Woodstock
Idyllic Woodstock, VT Cottage, vacation rental in Woodstock

Idyllic Woodstock, VT Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming and Chic Vacation Rental, vacation rental in Woodstock
Charming and Chic Vacation Rental, vacation rental in Woodstock
Charming and Chic Vacation Rental, vacation rental in Woodstock

Charming and Chic Vacation Rental

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Historic Ski Lodge on 112-Acre Vineyard, vacation rental in Woodstock
Historic Ski Lodge on 112-Acre Vineyard, vacation rental in Woodstock
Historic Ski Lodge on 112-Acre Vineyard, vacation rental in Woodstock

Historic Ski Lodge on 112-Acre Vineyard

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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South Woodstock Village, vacation rental in Woodstock
South Woodstock Village, vacation rental in Woodstock
South Woodstock Village, vacation rental in Woodstock

South Woodstock Village

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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12 Person Renovated Barn at Wise Pines- 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock
12 Person Renovated Barn at Wise Pines- 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock
12 Person Renovated Barn at Wise Pines- 5 minutes from downtown Woodstock, VT, vacation rental in Woodstock

12 Person Renovated Barn at Wise Pines- 5 minutes from downtown Woodstock, VT

Rental Home
2 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Dramatic Mountain Ridge Property In Woodstock, vacation rental in Woodstock
Dramatic Mountain Ridge Property In Woodstock, vacation rental in Woodstock
Dramatic Mountain Ridge Property In Woodstock, vacation rental in Woodstock

Dramatic Mountain Ridge Property In Woodstock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Ananda Vue- Lux 3BR/2BA hygge Villa w Fireplace and VIEWS!, vacation rental in Woodstock
Ananda Vue- Lux 3BR/2BA hygge Villa w Fireplace and VIEWS!, vacation rental in Woodstock
Ananda Vue- Lux 3BR/2BA hygge Villa w Fireplace and VIEWS!, vacation rental in Woodstock

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunlit VT Country Home w/Hot Tub.  Ideal location near Woodstock village, vacation rental in Woodstock
Sunlit VT Country Home w/Hot Tub.  Ideal location near Woodstock village, vacation rental in Woodstock
Sunlit VT Country Home w/Hot Tub.  Ideal location near Woodstock village, vacation rental in Woodstock

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village, vacation rental in Woodstock
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village, vacation rental in Woodstock
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village, vacation rental in Woodstock

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular  Views At This Luxury Country Estate, Walking Distance To Town, vacation rental in Woodstock
Spectacular  Views At This Luxury Country Estate, Walking Distance To Town, vacation rental in Woodstock
Spectacular  Views At This Luxury Country Estate, Walking Distance To Town, vacation rental in Woodstock

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect Woodstock Getaway! Lovely Riverside Home, vacation rental in Woodstock
Perfect Woodstock Getaway! Lovely Riverside Home, vacation rental in Woodstock
Perfect Woodstock Getaway! Lovely Riverside Home, vacation rental in Woodstock

Perfect Woodstock Getaway! Lovely Riverside Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Greydon Cabin ~ Rustic Luxury in Woodstock VT, vacation rental in Woodstock
Greydon Cabin ~ Rustic Luxury in Woodstock VT, vacation rental in Woodstock
Greydon Cabin ~ Rustic Luxury in Woodstock VT, vacation rental in Woodstock

Greydon Cabin ~ Rustic Luxury in Woodstock VT

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Contemporary Townhouse, vacation rental in Woodstock
Contemporary Townhouse, vacation rental in Woodstock
Contemporary Townhouse, vacation rental in Woodstock

Contemporary Townhouse

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge, vacation rental in Woodstock
Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge, vacation rental in Woodstock
Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge, vacation rental in Woodstock

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New! South Woodstock Cottage - restored, modern luxury, vacation rental in Woodstock
New! South Woodstock Cottage - restored, modern luxury, vacation rental in Woodstock
New! South Woodstock Cottage - restored, modern luxury, vacation rental in Woodstock

New! South Woodstock Cottage - restored, modern luxury

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Dog Friendly Home in S. Woodstock, vacation rental in Woodstock
Dog Friendly Home in S. Woodstock, vacation rental in Woodstock
Dog Friendly Home in S. Woodstock, vacation rental in Woodstock

Dog Friendly Home in S. Woodstock

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Vineyard House on 95 acres; a Perfect Spring to Autumn Playground, vacation rental in Woodstock
Vineyard House on 95 acres; a Perfect Spring to Autumn Playground, vacation rental in Woodstock
Vineyard House on 95 acres; a Perfect Spring to Autumn Playground, vacation rental in Woodstock

Vineyard House on 95 acres; a Perfect Spring to Autumn Playground

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hilltop Homestead : Charming Woodstock Farmhouse and Exquisite Gardens, vacation rental in Woodstock
Hilltop Homestead : Charming Woodstock Farmhouse and Exquisite Gardens, vacation rental in Woodstock
Hilltop Homestead : Charming Woodstock Farmhouse and Exquisite Gardens, vacation rental in Woodstock

Hilltop Homestead : Charming Woodstock Farmhouse and Exquisite Gardens

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Woodstock River Front, Sauna & Nature Trails, vacation rental in Woodstock
NEW! Woodstock River Front, Sauna & Nature Trails, vacation rental in Woodstock
NEW! Woodstock River Front, Sauna & Nature Trails, vacation rental in Woodstock

NEW! Woodstock River Front, Sauna & Nature Trails

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Yellow House on the Hill, 21 Acres, Views, Woodstock Getaway, Dog-friendly, vacation rental in Woodstock
Yellow House on the Hill, 21 Acres, Views, Woodstock Getaway, Dog-friendly, vacation rental in Woodstock
Yellow House on the Hill, 21 Acres, Views, Woodstock Getaway, Dog-friendly, vacation rental in Woodstock

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW Vermont Luxury in Woodstock Village: Private Home, Pond & Mountain Views, vacation rental in Woodstock
NEW Vermont Luxury in Woodstock Village: Private Home, Pond & Mountain Views, vacation rental in Woodstock
NEW Vermont Luxury in Woodstock Village: Private Home, Pond & Mountain Views, vacation rental in Woodstock

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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�Luxury Estate� 25 Gorgeous Acres of Privacy �Family Getaway�Swimming Pond�, vacation rental in Woodstock
�Luxury Estate� 25 Gorgeous Acres of Privacy �Family Getaway�Swimming Pond�, vacation rental in Woodstock
�Luxury Estate� 25 Gorgeous Acres of Privacy �Family Getaway�Swimming Pond�, vacation rental in Woodstock

�Luxury Estate� 25 Gorgeous Acres of Privacy �Family Getaway�Swimming Pond�

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury, private, peaceful home with Instagram worthy amenities!, vacation rental in Woodstock
Luxury, private, peaceful home with Instagram worthy amenities!, vacation rental in Woodstock
Luxury, private, peaceful home with Instagram worthy amenities!, vacation rental in Woodstock

Luxury, private, peaceful home with Instagram worthy amenities!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lovely, Spacious, Updated 1840s Home, Just 2 Blocks To Village Green., vacation rental in Woodstock
Lovely, Spacious, Updated 1840s Home, Just 2 Blocks To Village Green., vacation rental in Woodstock
Lovely, Spacious, Updated 1840s Home, Just 2 Blocks To Village Green., vacation rental in Woodstock

Lovely, Spacious, Updated 1840s Home, Just 2 Blocks To Village Green.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Chic Cabin near Killington for Relaxing and Co-working, vacation rental in Woodstock
Chic Cabin near Killington for Relaxing and Co-working, vacation rental in Woodstock
Chic Cabin near Killington for Relaxing and Co-working, vacation rental in Woodstock

Chic Cabin near Killington for Relaxing and Co-working

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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All Season, Open Plan Contemporary With Stunning Views, vacation rental in Woodstock
All Season, Open Plan Contemporary With Stunning Views, vacation rental in Woodstock
All Season, Open Plan Contemporary With Stunning Views, vacation rental in Woodstock

All Season, Open Plan Contemporary With Stunning Views

Rental Home
5 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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A charming 1820's farmhouse, vacation rental in Woodstock
A charming 1820's farmhouse, vacation rental in Woodstock
A charming 1820's farmhouse, vacation rental in Woodstock

A charming 1820's farmhouse

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Havenwood, a beautiful private, gated estate in Woodstock, Vermont, vacation rental in Woodstock
Havenwood, a beautiful private, gated estate in Woodstock, Vermont, vacation rental in Woodstock
Havenwood, a beautiful private, gated estate in Woodstock, Vermont, vacation rental in Woodstock

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

Rental Home
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Stay At Jimmy's, vacation rental in Woodstock
Stay At Jimmy's, vacation rental in Woodstock
Stay At Jimmy's, vacation rental in Woodstock

Stay At Jimmy's

Private Room
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Woodstock