Vacation rentals in Windsor, VT

Best vacation rentals and Airbnb offers in Windsor, VT

Studio 154 tucked away, peaceful and convenient access to the upper valley NH.

Apartment, Windsor

Studio 154 tucked away, peaceful and convenient access to the upper valley NH. is a apartment in Windsor, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Studio 154 tucked away, peaceful and convenient access to the upper valley NH.

Studio 154 tucked away, peaceful and convenient access to the upper valley NH. is a apartment in Windsor, 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 wifi, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $939.

From$134/night

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Spooner House

Farmhouse, Windsor

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

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About Spooner House

Spooner House is a farmhouse in Windsor, 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 $1,290.

From$165/night

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

Cabin, Windsor

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit is a cabin in Windsor, 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 Windsor, 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 $1,413.

From$202/night

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

Cabin, Windsor

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

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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, 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 $1,441.

From$206/night

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Vacation rentals with a pool in Windsor, VT

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

Golf Course, Natural Wood Fireplace - Greensway 3D

Condo, Windsor

Golf Course, Natural Wood Fireplace - Greensway 3D is a condo in Windsor, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Golf Course, Natural Wood Fireplace - Greensway 3D

Golf Course, Natural Wood Fireplace - Greensway 3D is a condo in Windsor, 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 $2,089.

From$298/night

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Highland Golf Course Getaway - Fairway Village 5B

Condo, Windsor

Highland Golf Course Getaway - Fairway Village 5B is a condo in Windsor, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Highland Golf Course Getaway - Fairway Village 5B

Highland Golf Course Getaway - Fairway Village 5B is a condo in Windsor, 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 $2,250.

From$321/night

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Villa with Games Room + Fitness Center Access

Villa, Windsor

Villa with Games Room + Fitness Center Access is a villa in Windsor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Villa with Games Room + Fitness Center Access

Villa with Games Room + Fitness Center Access is a villa in Windsor, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,266.

From$324/night

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Secluded farmhouse with private inground pool!

Country House, Windsor

Secluded farmhouse with private inground pool! is a country house in Windsor, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Secluded farmhouse with private inground pool!

Secluded farmhouse with private inground pool! is a country house in Windsor, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,822.

From$403/night

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Vacation rentals with parking in Windsor, VT

Find vacation rentals that make arriving by car easier.

Inn at Clearwater Pond (Quechee)

Guest House, Windsor

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

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About Inn at Clearwater Pond (Quechee)

Inn at Clearwater Pond (Quechee) is a guest house in Windsor, 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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Cozy 1-bedroom efficiency apartment in serene Lebanon with AC and gym space.

Apartment, Windsor

Cozy 1-bedroom efficiency apartment in serene Lebanon with AC and gym space. is a apartment in Windsor, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 1-bedroom efficiency apartment in serene Lebanon with AC and gym space.

Cozy 1-bedroom efficiency apartment in serene Lebanon with AC and gym space. is a apartment in Windsor, with parking, 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, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,549.

From$221/night

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Sleep Woodstock - Dog Friendly King Suite

B & B, Windsor

Sleep Woodstock - Dog Friendly King Suite is a b & b in Windsor, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite is a b & b in Windsor, 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 cancellation, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,127.

From$161/night

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Sleep Woodstock - Dog Friendly King Suite

B & B, Windsor

Sleep Woodstock - Dog Friendly King Suite is a b & b in Windsor, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite is a b & b in Windsor, 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 cancellation, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,127.

From$161/night

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Pet-friendly vacation rentals in Windsor, VT

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

Wood Road Retreat

Holiday Home, Windsor

Wood Road Retreat is a holiday home in Windsor, 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, 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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Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts

Cabin, Windsor

Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts is a cabin in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts

Designer Cabin With Solo Firepit Near Ski Trails - Ascutney Lofts is a cabin in Windsor, 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 $2,250.

From$321/night

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High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo

Cabin, Windsor

High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo is a cabin in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo

High-End Loft - Cozy Firepit, Hiking and Biking Trails, Near Okemo is a cabin in Windsor, 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 $2,276.

From$325/night

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Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger

Cabin, Windsor

Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger is a cabin in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger

Luxury Loft With Solo Fire Pit & Trails Close to Okemo & Ascutney EV Charger is a cabin in Windsor, 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 $2,279.

From$326/night

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Vacation rentals with a kitchen in Windsor, VT

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

2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area

Apartment, Windsor

2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area is a apartment in Windsor, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About 2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area

2-bedroom apartment with WiFi in charming Cavendish 6 miles from Okemo Ski Area is a apartment in Windsor, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,085.

From$155/night

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Spacious Downtown Studio | 10 Min to Sunapee

Apartment, Windsor

Spacious Downtown Studio · 10 Min to Sunapee is a apartment in Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Spacious Downtown Studio | 10 Min to Sunapee

Spacious Downtown Studio · 10 Min to Sunapee is a apartment in Windsor, 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 wifi, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,097.

From$157/night

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

Cabin, Windsor

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

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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 Windsor, 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 $1,452.

From$207/night

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Beautiful craftsman-built home with natural wood and large windows in every room

Holiday Home, Windsor

Beautiful craftsman-built home with natural wood and large windows in every room is a holiday home in Windsor, with kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful craftsman-built home with natural wood and large windows in every room

Beautiful craftsman-built home with natural wood and large windows in every room is a holiday home in Windsor, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,378.

From$340/night

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Family-friendly vacation rentals in Windsor, VT

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

The fireflies & waterfalls are calling! Book your Vermont Summer getaway now!

Holiday Home, Windsor

The fireflies & waterfalls are calling! Book your Vermont Summer getaway now! is a holiday home in Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring…

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About The fireflies & waterfalls are calling! Book your Vermont Summer getaway now!

The fireflies & waterfalls are calling! Book your Vermont Summer getaway now! is a holiday home in Windsor, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,557.

From$222/night

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Cabin is nestled near the Sugar River in a country setting next to a open field.

Cabin, Windsor

Cabin is nestled near the Sugar River in a country setting next to a open field. is a cabin in Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cabin is nestled near the Sugar River in a country setting next to a open field.

Cabin is nestled near the Sugar River in a country setting next to a open field. is a cabin in Windsor, 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 $1,757.

From$251/night

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Woodstock Village Carriage House

Cottage, Windsor

Woodstock Village Carriage House is a cottage in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Woodstock Village Carriage House

Woodstock Village Carriage House is a cottage in Windsor, 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 $1,990.

From$284/night

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Romantic Getaway or Family winter adventures in 2BD w/resort activities

Condo, Windsor

Romantic Getaway or Family winter adventures in 2BD w/resort activities is a condo in Windsor, with pool access and room for a group. This stay gives travelers a comfortable base for…

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About Romantic Getaway or Family winter adventures in 2BD w/resort activities

Romantic Getaway or Family winter adventures in 2BD w/resort activities is a condo in Windsor, with pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,643.

From$378/night

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