Vacation rentals in Western Massachusetts, MA

Best Vacation rentals and Airbnb offers in Western Massachusetts, MA

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Holiday Home, Western Massachusetts

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts is a holiday home in Western Massachusetts, with pet-friendly space. This stay gives travelers a comfortable…

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About Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts is a holiday home in Western Massachusetts, 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, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $606.

From$76/night

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

Holiday Home, Western Massachusetts

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

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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 Western Massachusetts, 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 $792.

From$95/night

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Unique and Eclectic Small Town Suite Rental in Massachusetts

Holiday Home, Western Massachusetts

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

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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 Western Massachusetts, 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 $781.

From$95/night

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Magical yurt in the woods, full kitchen! Haydenville, Massechusettes

Cabin, Western Massachusetts

Magical yurt in the woods, full kitchen! Haydenville, Massechusettes is a cabin in Western Massachusetts, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Magical yurt in the woods, full kitchen! Haydenville, Massechusettes

Magical yurt in the woods, full kitchen! Haydenville, Massechusettes is a cabin in Western Massachusetts, 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 $824.

From$98/night

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Best Western Massachusetts, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Riverfront Log Home on 44 Acres with Sauna

Holiday Home, Western Massachusetts

Riverfront Log Home on 44 Acres with Sauna is a holiday home in Western Massachusetts, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Riverfront Log Home on 44 Acres with Sauna

Riverfront Log Home on 44 Acres with Sauna is a holiday home in Western Massachusetts, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,588.

From$240/night

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Luxury log cabin with views to Mt. Monadnock

Holiday Home, Western Massachusetts

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

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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 Western Massachusetts, 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 $2,844.

From$305/night

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Lakes & Leisure! Spacious Berkshire Getaway

Holiday Home, Western Massachusetts

Lakes & Leisure! Spacious Berkshire Getaway is a holiday home in Western Massachusetts, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lakes & Leisure! Spacious Berkshire Getaway

Lakes & Leisure! Spacious Berkshire Getaway is a holiday home in Western Massachusetts, 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 $3,439.

From$320/night

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Lake House In The Heart Of The Berkshires

Holiday Home, Western Massachusetts

Lake House In The Heart Of The Berkshires is a holiday home in Western Massachusetts, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Lake House In The Heart Of The Berkshires

Lake House In The Heart Of The Berkshires is a holiday home in Western Massachusetts, 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 $6,809.

From$713/night

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Best Pet-Friendly Vacation Rentals in Western Massachusetts, MA

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

Cozy Country Home in Conway

Holiday Home, Western Massachusetts

Cozy Country Home in Conway is a holiday home in Western Massachusetts, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Country Home in Conway

Cozy Country Home in Conway is a holiday home in Western Massachusetts, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,433.

From$270/night

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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Holiday Home, Western Massachusetts

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow is a holiday home in Western Massachusetts, with pet-friendly space, kitchen access, and a quieter setting. This stay gives…

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About Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow is a holiday home in Western Massachusetts, 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 $3,606.

From$395/night

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Massachusetts Vacation Rental w/ Deck & Grill

Holiday Home, Western Massachusetts

Massachusetts Vacation Rental w/ Deck & Grill is a holiday home in Western Massachusetts, with pet-friendly space, outdoor space, and parking. 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 holiday home in Western Massachusetts, 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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Our Favorite Family-Friendly Vacation Rentals in Western Massachusetts, MA

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

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!

Cottage, Western Massachusetts

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! is a cottage in Western Massachusetts, with parking and room for a group. This stay gives travelers a…

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About Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! is a cottage in Western Massachusetts, with parking 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,087.

From$250/night

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Historic Huntington Home - Walk to Westfield River

Cottage, Western Massachusetts

Historic Huntington Home - Walk to Westfield River is a cottage in Western Massachusetts, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River is a cottage in Western Massachusetts, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,206.

From$272/night

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New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond

Holiday Home, Western Massachusetts

New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond is a holiday home in Western Massachusetts, with outdoor space. This stay gives travelers a comfortable base…

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About New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond

New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond is a holiday home in Western Massachusetts, with outdoor 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, fireplace, non smoking, and patio.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,989.

From$300/night

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Massachusetts Vacation Rental w/ Deck & Grill

Cottage, Western Massachusetts

Massachusetts Vacation Rental w/ Deck & Grill is a cottage in Western Massachusetts, 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 Western Massachusetts, 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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