Vacation rentals in South Woodstock, VT

200 available vacation rental offers

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Best Vacation rentals and Airbnb offers in South Woodstock, VT

2br duplex 10 minutes to Killington and 10 minutes to Woodstock - South Woodstock, VT

2br duplex 10 minutes to Killington and 10 minutes to Woodstock

Holiday Home, South Woodstock

2br duplex 10 minutes to Killington and 10 minutes to Woodstock is a holiday home in South Woodstock, with room for a group. This stay gives travelers a comfortable base for exploring the…

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About 2br duplex 10 minutes to Killington and 10 minutes to Woodstock

2br duplex 10 minutes to Killington and 10 minutes to Woodstock is a holiday home in South Woodstock, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,312.

From$132/night
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Wood Road Retreat - South Woodstock, VT

Wood Road Retreat

Holiday Home, South Woodstock

Wood Road Retreat is a holiday home in South Woodstock, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Wood Road Retreat

Wood Road Retreat is a holiday home in South Woodstock, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,875.

From$165/night
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Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental - South Woodstock, VT

Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental

Holiday Home, South Woodstock

Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental is a holiday home in South Woodstock, with pet-friendly space and room for a group. This stay gives travelers a comfortable…

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About Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental

Family, Pet Friendly Bridgewater/Killington/Woodstock Area Rental is a holiday home in South Woodstock, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, non smoking, non smoking::all, and non smoking everywhere.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,313.

From$171/night
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Cozy cottage on the river, minutes from skiing, horse events, and so much more! - South Woodstock, VT

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Cottage, South Woodstock

Cozy cottage on the river, minutes from skiing, horse events, and so much more! is a cottage in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable…

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About Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Cozy cottage on the river, minutes from skiing, horse events, and so much more! is a cottage in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,644.

From$180/night
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Browse Vacation Rentals with a Pool in South Woodstock, VT

Add a pool to the search when you want an easy place to cool off between outings.

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Fireplace, Sauna - South Woodstock, VT

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Fireplace, Sauna

Holiday Home, South Woodstock

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Fireplace, Sauna is a holiday home in South Woodstock, with pool access. This stay gives travelers a comfortable base for…

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About ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Fireplace, Sauna

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Fireplace, Sauna is a holiday home in South Woodstock, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,349.

From$131/night
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Renovated Condo, Heart of Quechee - Mill Run 3E - South Woodstock, VT

Renovated Condo, Heart of Quechee - Mill Run 3E

Condo, South Woodstock

Renovated Condo, Heart of Quechee - Mill Run 3E is a condo in South Woodstock, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Renovated Condo, Heart of Quechee - Mill Run 3E

Renovated Condo, Heart of Quechee - Mill Run 3E is a condo in South Woodstock, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,434.

From$133/night
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Kingswood 1D: Ski-In/Ski-Out Condo w/ Deck & Views - South Woodstock, VT

Kingswood 1D: Ski-In/Ski-Out Condo w/ Deck & Views

Condo, South Woodstock

Kingswood 1D: Ski-In/Ski-Out Condo w/ Deck & Views is a condo in South Woodstock, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Kingswood 1D: Ski-In/Ski-Out Condo w/ Deck & Views

Kingswood 1D: Ski-In/Ski-Out Condo w/ Deck & Views is a condo in South Woodstock, with pool access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,840.

From$156/night
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Cozy Quechee Retreat/Walk to Village | Mill Run 4A - South Woodstock, VT

Cozy Quechee Retreat/Walk to Village | Mill Run 4A

Condo, South Woodstock

Cozy Quechee Retreat/Walk to Village · Mill Run 4A is a condo in South Woodstock, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy Quechee Retreat/Walk to Village | Mill Run 4A

Cozy Quechee Retreat/Walk to Village · Mill Run 4A is a condo in South Woodstock, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,924.

From$184/night
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Best South Woodstock, VT vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit - South Woodstock, VT

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cabin, South Woodstock

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit is a cabin in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit is a cabin in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,583.

From$167/night
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Large Backyard, Game Room, Has AC - Saltbox 1D - South Woodstock, VT

Large Backyard, Game Room, Has AC - Saltbox 1D

Condo, South Woodstock

Large Backyard, Game Room, Has AC - Saltbox 1D is a condo in South Woodstock, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Large Backyard, Game Room, Has AC - Saltbox 1D

Large Backyard, Game Room, Has AC - Saltbox 1D is a condo in South Woodstock, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,072.

From$189/night
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Vermont Villa Near the Trails - South Woodstock, VT

Vermont Villa Near the Trails

Villa, South Woodstock

Vermont Villa Near the Trails is a villa in South Woodstock, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Vermont Villa Near the Trails

Vermont Villa Near the Trails is a villa in South Woodstock, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,638.

From$190/night
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Inn at Clearwater Pond (Quechee) - South Woodstock, VT

Inn at Clearwater Pond (Quechee)

Guest House, South Woodstock

Inn at Clearwater Pond (Quechee) is a guest house in South Woodstock, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Inn at Clearwater Pond (Quechee)

Inn at Clearwater Pond (Quechee) is a guest house in South Woodstock, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, free wifi, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,617.

From$210/night
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Best Pet-Friendly Vacation Rentals in South Woodstock, VT

Bring your pet along with stays that welcome four-legged travelers.

Custom-built Tiny House on forested lot near Quechee - South Woodstock, VT

Custom-built Tiny House on forested lot near Quechee

Holiday Home, South Woodstock

Custom-built Tiny House on forested lot near Quechee is a holiday home in South Woodstock, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Custom-built Tiny House on forested lot near Quechee

Custom-built Tiny House on forested lot near Quechee is a holiday home in South Woodstock, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,789.

From$187/night
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Walk to Trails & Village +Pets - Highland Cabin - South Woodstock, VT

Walk to Trails & Village +Pets - Highland Cabin

Holiday Home, South Woodstock

Walk to Trails & Village +Pets - Highland Cabin is a holiday home in South Woodstock, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Walk to Trails & Village +Pets - Highland Cabin

Walk to Trails & Village +Pets - Highland Cabin is a holiday home in South Woodstock, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,720.

From$273/night
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18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch - South Woodstock, VT

18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch

Country House, South Woodstock

18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch is a country house in South Woodstock, with pet-friendly space and parking. This stay gives travelers a…

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About 18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch

18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch is a country house in South Woodstock, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,938.

From$315/night
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PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. - South Woodstock, VT

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

Holiday Home, South Woodstock

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. is a holiday home in South Woodstock, with pet-friendly space and kitchen access. This stay gives travelers a…

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About PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. is a holiday home in South Woodstock, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,262.

From$338/night
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Best South Woodstock, VT vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit - South Woodstock, VT

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cabin, South Woodstock

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit is a cabin in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit is a cabin in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,673.

From$177/night
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Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit - South Woodstock, VT

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cabin, South Woodstock

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit is a cabin in South Woodstock, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit is a cabin in South Woodstock, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,770.

From$188/night
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Next to Golf, Walk to Club - Lakeland Village 5B - South Woodstock, VT

Next to Golf, Walk to Club - Lakeland Village 5B

Condo, South Woodstock

Next to Golf, Walk to Club - Lakeland Village 5B is a condo in South Woodstock, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Next to Golf, Walk to Club - Lakeland Village 5B

Next to Golf, Walk to Club - Lakeland Village 5B is a condo in South Woodstock, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,224.

From$205/night
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Charming King Loft in Downtown Woodstock - South Woodstock, VT

Charming King Loft in Downtown Woodstock

Apartment, South Woodstock

Charming King Loft in Downtown Woodstock is a apartment in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming King Loft in Downtown Woodstock

Charming King Loft in Downtown Woodstock is a apartment in South Woodstock, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,366.

From$255/night
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Our Favorite Family-Friendly Vacation Rentals in South Woodstock, VT

Plan a trip with stays that give families more room to spread out.

Ski & Mountain Getaway-Minutes to Okemo, Killington, Long Trail, and many lakes! - South Woodstock, VT

Ski & Mountain Getaway-Minutes to Okemo, Killington, Long Trail, and many lakes!

Condo, South Woodstock

Ski & Mountain Getaway-Minutes to Okemo, Killington, Long Trail, and many lakes! is a condo in South Woodstock, with kitchen access. This stay gives travelers a comfortable base for…

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About Ski & Mountain Getaway-Minutes to Okemo, Killington, Long Trail, and many lakes!

Ski & Mountain Getaway-Minutes to Okemo, Killington, Long Trail, and many lakes! is a condo in South Woodstock, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,447.

From$108/night
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Spooner House - South Woodstock, VT

Spooner House

Farmhouse, South Woodstock

Spooner House is a farmhouse in South Woodstock, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Spooner House

Spooner House is a farmhouse in South Woodstock, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,279.

From$163/night
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Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC - South Woodstock, VT

Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC

Cottage, South Woodstock

Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC is a cottage in South Woodstock, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC

Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC is a cottage in South Woodstock, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,271.

From$225/night
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All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC - South Woodstock, VT

All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC

Cottage, South Woodstock

All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC is a cottage in South Woodstock, with room for a group. This stay gives travelers a comfortable base for exploring the…

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About All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC

All New 1-bedroom cottage on a private pond in Woodstock with WiFi, AC is a cottage in South Woodstock, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,259.

From$239/night
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