Vacation rentals in Windsor Jambs Road, MA

Best vacation rentals and Airbnb offers in Windsor Jambs Road, MA

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Apartment, Windsor Jambs Road

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown is a apartment in Windsor Jambs Road, with parking, kitchen access, and room for a group. This stay gives…

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About Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown is a apartment in Windsor Jambs Road, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,087.

From$155/night

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

Holiday Home, Windsor Jambs Road

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

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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 Jambs Road, 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 $1,236.

From$177/night

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

Cottage, Windsor Jambs Road

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort is a cottage in Windsor Jambs Road, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable…

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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 cottage in Windsor Jambs Road, 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 $1,491.

From$184/night

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Golf House by Mt Greylock - Walkable Adventures!

Holiday Home, Windsor Jambs Road

Golf House by Mt Greylock - Walkable Adventures! is a holiday home in Windsor Jambs Road, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the…

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About Golf House by Mt Greylock - Walkable Adventures!

Golf House by Mt Greylock - Walkable Adventures! is a holiday home in Windsor Jambs Road, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,628.

From$233/night

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Vacation rentals with parking in Windsor Jambs Road, MA

Find vacation rentals that make arriving by car easier.

Harbour House Inn B&B

B & B, Windsor Jambs Road

Harbour House Inn B&B is a b & b in Windsor Jambs Road, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Harbour House Inn B&B

Harbour House Inn B&B is a b & b in Windsor Jambs Road, 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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Harbour House Inn B&B

B & B, Windsor Jambs Road

Harbour House Inn B&B is a b & b in Windsor Jambs Road, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Harbour House Inn B&B

Harbour House Inn B&B is a b & b in Windsor Jambs Road, 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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Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown

Holiday Home, Windsor Jambs Road

Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown is a holiday home in Windsor Jambs Road, with parking and kitchen access. This stay gives travelers a comfortable…

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About Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown

Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown is a holiday home in Windsor Jambs Road, 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 $1,948.

From$278/night

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The Trail in Adams - Berkshires’ Art Hotel

B & B, Windsor Jambs Road

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

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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 Jambs Road, 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 Jambs Road, MA

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

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

Holiday Home, Windsor Jambs Road

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

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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 Jambs Road, 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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Charming Retreat by Mass MoCA

Holiday Home, Windsor Jambs Road

Charming Retreat by Mass MoCA is a holiday home in Windsor Jambs Road, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Charming Retreat by Mass MoCA

Charming Retreat by Mass MoCA is a holiday home in Windsor Jambs Road, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,559.

From$366/night

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Relaxing Mountaintop Retreat in the Northern Berkshires

Holiday Home, Windsor Jambs Road

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

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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 Jambs Road, 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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Massachusetts Vacation Rental w/ Deck & Grill

Holiday Home, Windsor Jambs Road

Massachusetts Vacation Rental w/ Deck & Grill is a holiday home in Windsor Jambs Road, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill is a holiday home in Windsor Jambs Road, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,561.

From$560/night

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Vacation rentals with a kitchen in Windsor Jambs Road, 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 Jambs Road

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

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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 Jambs Road, 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 Condo Near MASS MoCA

Holiday Home, Windsor Jambs Road

Cozy Condo Near MASS MoCA is a holiday home in Windsor Jambs Road, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Condo Near MASS MoCA

Cozy Condo Near MASS MoCA is a holiday home in Windsor Jambs Road, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,513.

From$359/night

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Luxury log cabin with views to Mt. Monadnock

Holiday Home, Windsor Jambs Road

Luxury log cabin with views to Mt. Monadnock is a holiday home in Windsor Jambs Road, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Luxury log cabin with views to Mt. Monadnock

Luxury log cabin with views to Mt. Monadnock is a holiday home in Windsor Jambs Road, 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 $2,546.

From$364/night

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Art House! Spacious Getaway By Mass Moca

Holiday Home, Windsor Jambs Road

Art House! Spacious Getaway By Mass Moca is a holiday home in Windsor Jambs Road, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Art House! Spacious Getaway By Mass Moca

Art House! Spacious Getaway By Mass Moca is a holiday home in Windsor Jambs Road, 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 $3,031.

From$433/night

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Family-friendly vacation rentals in Windsor Jambs Road, MA

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

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

Holiday Home, Windsor Jambs Road

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

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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 Jambs Road, 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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Near Berkshire East | River Farmhouse on 10 Acres

Holiday Home, Windsor Jambs Road

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

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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 Jambs Road, 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 $2,823.

From$403/night

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Berkshire's Family Gathering & Mountain Escape!

Holiday Home, Windsor Jambs Road

Berkshire's Family Gathering & Mountain Escape! is a holiday home in Windsor Jambs Road, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Berkshire's Family Gathering & Mountain Escape!

Berkshire's Family Gathering & Mountain Escape! is a holiday home in Windsor Jambs Road, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,106.

From$587/night

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Massachusetts Vacation Rental w/ Deck & Grill

Cottage, Windsor Jambs Road

Massachusetts Vacation Rental w/ Deck & Grill is a cottage in Windsor Jambs Road, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base…

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About Massachusetts Vacation Rental w/ Deck & Grill

Massachusetts Vacation Rental w/ Deck & Grill is a cottage in Windsor Jambs Road, 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 $4,732.

From$609/night

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