Vacation rentals in Chesterfield, MA

22 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Chesterfield, MA

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts - Chesterfield, MA

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Holiday Home, Chesterfield

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

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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 Chesterfield, 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 - Chesterfield, MA

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

Holiday Home, Chesterfield

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts is a holiday home in Chesterfield, 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 Chesterfield, 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 - Chesterfield, MA

Unique and Eclectic Small Town Suite Rental in Massachusetts

Holiday Home, Chesterfield

Unique and Eclectic Small Town Suite Rental in Massachusetts is a holiday home in Chesterfield, 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 Chesterfield, 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 - Chesterfield, MA

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

Cabin, Chesterfield

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

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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 Chesterfield, 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 Chesterfield, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Luxury log cabin with views to Mt. Monadnock - Chesterfield, MA

Luxury log cabin with views to Mt. Monadnock

Holiday Home, Chesterfield

Luxury log cabin with views to Mt. Monadnock is a holiday home in Chesterfield, 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 Chesterfield, 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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Gorgeous Timber Frame Home in Ashfield - 4 bedrooms, 3 bathrooms and Sauna - Chesterfield, MA

Gorgeous Timber Frame Home in Ashfield - 4 bedrooms, 3 bathrooms and Sauna

Country House, Chesterfield

Gorgeous Timber Frame Home in Ashfield - 4 bedrooms, 3 bathrooms and Sauna is a country house in Chesterfield, with parking and room for a group. This stay gives travelers a comfortable…

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About Gorgeous Timber Frame Home in Ashfield - 4 bedrooms, 3 bathrooms and Sauna

Gorgeous Timber Frame Home in Ashfield - 4 bedrooms, 3 bathrooms and Sauna is a country house in Chesterfield, 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, free wifi, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,180.

From$450/night
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Cozy Valley View Post & Beam Villa! - Chesterfield, MA

Cozy Valley View Post & Beam Villa!

Villa, Chesterfield

Cozy Valley View Post & Beam Villa! is a villa in Chesterfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa! is a villa in Chesterfield, 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 $7,731.

From$873/night
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Best Pet-Friendly Vacation Rentals in Chesterfield, MA

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

Cozy Country Home in Conway - Chesterfield, MA

Cozy Country Home in Conway

Holiday Home, Chesterfield

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

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About Cozy Country Home in Conway

Cozy Country Home in Conway is a holiday home in Chesterfield, 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 - Chesterfield, MA

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Holiday Home, Chesterfield

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

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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 Chesterfield, 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 - Chesterfield, MA

Massachusetts Vacation Rental w/ Deck & Grill

Holiday Home, Chesterfield

Massachusetts Vacation Rental w/ Deck & Grill is a holiday home in Chesterfield, 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 Chesterfield, 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 Chesterfield, 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! - Chesterfield, MA

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

Cottage, Chesterfield

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

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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 Chesterfield, 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 - Chesterfield, MA

Historic Huntington Home - Walk to Westfield River

Cottage, Chesterfield

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

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About Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River is a cottage in Chesterfield, 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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Massachusetts Vacation Rental w/ Deck & Grill - Chesterfield, MA

Massachusetts Vacation Rental w/ Deck & Grill

Cottage, Chesterfield

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

Read more

About Massachusetts Vacation Rental w/ Deck & Grill

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