Vacation rentals in Windsor, MA

Best vacation rentals and Airbnb offers in Windsor, MA

Unique and Eclectic Small Town Suite Rental in Massachusetts

Holiday Home, Windsor

Unique and Eclectic Small Town Suite Rental in Massachusetts is a holiday home in Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts is a holiday home in Windsor, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $749.

From$107/night

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Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Holiday Home, Windsor

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts is a holiday home in Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts is a holiday home in Windsor, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $759.

From$108/night

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Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, Windsor

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Windsor, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi 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: parking, free parking, washer, and dryer.

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

From$155/night

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Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Holiday Home, Windsor

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a holiday home in Windsor, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a holiday home in Windsor, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,238.

From$177/night

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Vacation rentals with a pool in Windsor, MA

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

Comfortable Berkshires retreat on mtn resort, SISO

Holiday Home, Windsor

Comfortable Berkshires retreat on mtn resort, SISO is a holiday home in Windsor, with pool access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO is a holiday home in Windsor, with pool 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,751.

From$393/night

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3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Condo, Windsor

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY 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 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,325.

From$475/night

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Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

Holiday Home, Windsor

Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak is a holiday home in Windsor, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak is a holiday home in Windsor, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,904.

From$558/night

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Large Mountainside Condo with Private Trail to Grouse Run

Condo, Windsor

Large Mountainside Condo with Private Trail to Grouse Run is a condo in Windsor, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Large Mountainside Condo with Private Trail to Grouse Run

Large Mountainside Condo with Private Trail to Grouse Run is a condo in Windsor, 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 $6,264.

From$895/night

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Vacation rentals with parking in Windsor, MA

Find vacation rentals that make arriving by car easier.

The Central Downtown Inn & Suites

Guest House, Windsor

The Central Downtown Inn & Suites 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 The Central Downtown Inn & Suites

The Central Downtown Inn & Suites 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 wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,925.

From$246/night

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Harbour House Inn B&B

B & B, Windsor

Harbour House Inn B&B is a b & b in Windsor, with parking. 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 Harbour House Inn B&B

Harbour House Inn B&B is a b & b 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 breakfast, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,915.

From$259/night

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Harbour House Inn B&B

B & B, Windsor

Harbour House Inn B&B is a b & b in Windsor, with parking. 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 Harbour House Inn B&B

Harbour House Inn B&B is a b & b 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 breakfast, free wifi, parking, paid parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,915.

From$259/night

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The Trail in Adams - Berkshires’ Art Hotel

B & B, Windsor

The Trail in Adams - Berkshires’ Art Hotel is a b & b in Windsor, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel is a b & b 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,287.

From$293/night

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Pet-friendly vacation rentals in Windsor, MA

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

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Apartment, Windsor

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Windsor, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,264.

From$181/night

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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Holiday Home, Windsor

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort is a holiday home in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort is a holiday home 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 $1,663.

From$238/night

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Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Holiday Home, Windsor

Cozy Home In The Berkshires, Pet Friendly with fenced in yard! is a holiday home in Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard! is a holiday home in Windsor, 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 $2,085.

From$298/night

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Near Berkshire East | River Farmhouse on 10 Acres

Holiday Home, Windsor

Near Berkshire East · River Farmhouse on 10 Acres is a holiday home in Windsor, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Near Berkshire East | River Farmhouse on 10 Acres

Near Berkshire East · River Farmhouse on 10 Acres is a holiday home in Windsor, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,843.

From$406/night

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Vacation rentals with a kitchen in Windsor, MA

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

Come stay with us at the Parsonage and enjoy our mountains and rivers.

Country House, Windsor

Come stay with us at the Parsonage and enjoy our mountains and rivers. is a country house in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Come stay with us at the Parsonage and enjoy our mountains and rivers.

Come stay with us at the Parsonage and enjoy our mountains and rivers. is a country house 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 $2,412.

From$345/night

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Cozy Home in Lenox

Holiday Home, Windsor

Cozy Home in Lenox 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…

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About Cozy Home in Lenox

Cozy Home in Lenox 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,779.

From$397/night

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Solomon Ely Homestead - Charming Pittsfield Stay

Holiday Home, Windsor

Solomon Ely Homestead - Charming Pittsfield Stay is a holiday home in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Solomon Ely Homestead - Charming Pittsfield Stay

Solomon Ely Homestead - Charming Pittsfield Stay is a holiday home 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 $3,023.

From$432/night

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Relaxing Mountaintop Retreat in the Northern Berkshires

Holiday Home, Windsor

Relaxing Mountaintop Retreat in the Northern Berkshires is a holiday home in Windsor, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Relaxing Mountaintop Retreat in the Northern Berkshires

Relaxing Mountaintop Retreat in the Northern Berkshires is a holiday home 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,626.

From$518/night

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Family-friendly vacation rentals in Windsor, MA

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

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Cottage, Windsor

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! is a cottage in Windsor, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Hawley Home w/ Deck & Mtn Views: Swim, Ski & More!

Hawley Home w/ Deck & Mtn Views: Swim, Ski & More! is a cottage in Windsor, with pet-friendly space, outdoor 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 $2,001.

From$242/night

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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Holiday Home, Windsor

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home in Windsor, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,744.

From$249/night

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2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Holiday Home, Windsor

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox is a holiday home in Windsor, with pet-friendly space and room for a group. This stay gives travelers a…

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About 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox is a holiday home in Windsor, 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: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,287.

From$327/night

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Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Holiday Home, Windsor

Cozy Cottage in Berkshires: Minutes to Jiminy Peak is a holiday home in Windsor, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Cozy Cottage in Berkshires: Minutes to Jiminy Peak 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,663.

From$380/night

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