Vacation rentals in Windsor County, VT

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Windsor County, VT

Valkyrie Run - Windsor County, VT

Valkyrie Run

Holiday Home, Windsor County

Valkyrie Run is a holiday home in Windsor County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Valkyrie Run

Valkyrie Run is a holiday home in Windsor County, 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: free wifi, pet friendly, pets friendly, parking, and paid parking.

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

From$127/night
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Wood Road Retreat - Windsor County, VT

Wood Road Retreat

Holiday Home, Windsor County

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

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About Wood Road Retreat

Wood Road Retreat is a holiday home in Windsor County, 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 $1,834.

From$160/night
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2br duplex 10 minutes to Killington and 10 minutes to Woodstock - Windsor County, VT

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

Holiday Home, Windsor County

2br duplex 10 minutes to Killington and 10 minutes to Woodstock is a holiday home in Windsor County, 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 Windsor County, 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 $1,171.

From$167/night
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Cozy cottage on the river, minutes from skiing, horse events, and so much more! - Windsor County, VT

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

Cottage, Windsor County

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

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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 Windsor County, 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 $1,468.

From$210/night
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Vacation rentals with a pool in Windsor County, VT

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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail - Windsor County, VT

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cabin, Windsor County

Ski in & out Spruce Glen Townhomes on Great Eastern Trail is a cabin in Windsor County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

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About Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail is a cabin in Windsor County, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,370.

From$161/night
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Ski in/out Spruce Glen Townhomes on Great Eastern Trail - Windsor County, VT

Ski in/out Spruce Glen Townhomes on Great Eastern Trail

Holiday Home, Windsor County

Ski in/out Spruce Glen Townhomes on Great Eastern Trail is a holiday home in Windsor County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About Ski in/out Spruce Glen Townhomes on Great Eastern Trail

Ski in/out Spruce Glen Townhomes on Great Eastern Trail is a holiday home in Windsor County, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,412.

From$163/night
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Cedarbrook Queen Suite 103 - Windsor County, VT

Cedarbrook Queen Suite 103

Apartment, Windsor County

Cedarbrook Queen Suite 103 is a apartment in Windsor County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cedarbrook Queen Suite 103

Cedarbrook Queen Suite 103 is a apartment in Windsor County, 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: pool, free wifi, and ourdoor pool.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,416.

From$165/night
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Cedarbrook Two Queen Bed Standard Hotel Room with outdoor heated pool 102 - Windsor County, VT

Cedarbrook Two Queen Bed Standard Hotel Room with outdoor heated pool 102

Apartment, Windsor County

Cedarbrook Two Queen Bed Standard Hotel Room with outdoor heated pool 102 is a apartment in Windsor County, with pool access. This stay gives travelers a comfortable base for exploring the…

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About Cedarbrook Two Queen Bed Standard Hotel Room with outdoor heated pool 102

Cedarbrook Two Queen Bed Standard Hotel Room with outdoor heated pool 102 is a apartment in Windsor County, 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: pool, free wifi, and ourdoor pool.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,431.

From$165/night
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Vacation rentals with parking in Windsor County, VT

Find vacation rentals that make arriving by car easier.

375 Hawk Spur - Windsor County, VT

375 Hawk Spur

Holiday Home, Windsor County

375 Hawk Spur is a holiday home in Windsor County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About 375 Hawk Spur

375 Hawk Spur is a holiday home in Windsor County, 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: hot tub, parking, paid parking, non smoking::room, and non smoking rooms.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,750.

From$159/night
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Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102 - Windsor County, VT

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Apartment, Windsor County

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102 is a apartment in Windsor County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102

Cedarbrook Deluxe 1 bedroom Queen Suite with outdoor heated pool 102 is a apartment in Windsor County, 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, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,276.

From$182/night
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Saltbox 12A - Windsor County, VT

Saltbox 12A

Holiday Home, Windsor County

Saltbox 12A is a holiday home in Windsor County, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Saltbox 12A

Saltbox 12A is a holiday home in Windsor County, with pool access 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: pool, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,980.

From$191/night
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Charming King Loft in Downtown Woodstock - Windsor County, VT

Charming King Loft in Downtown Woodstock

Apartment, Windsor County

Charming King Loft in Downtown Woodstock is a apartment in Windsor County, 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 Windsor County, 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 $2,100.

From$300/night
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Pet-friendly vacation rentals in Windsor County, VT

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

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen - Windsor County, VT

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

Holiday Home, Windsor County

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen is a holiday home in Windsor County, with pet-friendly space, kitchen access, and a quieter setting. This stay gives…

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About Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen is a holiday home in Windsor County, with pet-friendly space, kitchen access, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,171.

From$310/night
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18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch - Windsor County, VT

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

Country House, Windsor County

18-Acres in Woodstock - Pet-Friendly, Trails, Brook, Fireplace, Screened Porch is a country house in Windsor County, 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 Windsor County, 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 $2,600.

From$371/night
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PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. - Windsor County, VT

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

Holiday Home, Windsor County

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC. is a holiday home in Windsor County, 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 Windsor County, 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 $2,887.

From$412/night
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5BR Chalet in Historic Town bet Killington & Okemo - Windsor County, VT

5BR Chalet in Historic Town bet Killington & Okemo

Chalet, Windsor County

5BR Chalet in Historic Town bet Killington & Okemo is a chalet in Windsor County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About 5BR Chalet in Historic Town bet Killington & Okemo

5BR Chalet in Historic Town bet Killington & Okemo is a chalet in Windsor County, with pet-friendly space, kitchen access, 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: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,528.

From$218/night
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Vacation rentals with a kitchen in Windsor County, VT

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

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool - Windsor County, VT

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

Apartment, Windsor County

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool is a apartment in Windsor County, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About 103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool is a apartment in Windsor County, with pool access, kitchen access, 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: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,276.

From$182/night
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Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit - Windsor County, VT

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

Cabin, Windsor County

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit is a cabin in Windsor County, 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 Windsor County, 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 $1,447.

From$207/night
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Kingswood 1D: Ski-In/Ski-Out Condo w/ Deck & Views - Windsor County, VT

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

Condo, Windsor County

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

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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 Windsor County, 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 $1,621.

From$232/night
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Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes. - Windsor County, VT

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Holiday Home, Windsor County

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes. is a holiday home in Windsor County, with kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes. is a holiday home in Windsor County, 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, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,997.

From$285/night
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Family-friendly vacation rentals in Windsor County, 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! - Windsor County, VT

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

Condo, Windsor County

Ski & Mountain Getaway-Minutes to Okemo, Killington, Long Trail, and many lakes! is a condo in Windsor County, 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 Windsor County, 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 $1,292.

From$185/night
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Snowledge II by Okemo/Killington - Windsor County, VT

Snowledge II by Okemo/Killington

Holiday Home, Windsor County

Snowledge II by Okemo/Killington is a holiday home in Windsor County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Snowledge II by Okemo/Killington

Snowledge II by Okemo/Killington is a holiday home in Windsor County, 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 $1,799.

From$257/night
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Swim, Ski & Sip: Lakefront Retreat in Plymouth - Windsor County, VT

Swim, Ski & Sip: Lakefront Retreat in Plymouth

Cottage, Windsor County

Swim, Ski & Sip: Lakefront Retreat in Plymouth is a cottage in Windsor County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Swim, Ski & Sip: Lakefront Retreat in Plymouth

Swim, Ski & Sip: Lakefront Retreat in Plymouth is a cottage in Windsor County, with parking, kitchen access, 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,337.

From$267/night
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Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC - Windsor County, VT

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

Cottage, Windsor County

Mountain Hilltop Retreat: Cozy 2-bedroom cottage in serene Bridgewater with AC is a cottage in Windsor County, 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 Windsor County, 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 $2,028.

From$290/night
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