Vacation rentals in Southampton, MA

49 available vacation rental offers

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Best vacation rentals and Airbnb offers in Southampton, MA

3 Mi to Dtwn Springfield: Winter Retreat w/ Office - Southampton, MA

3 Mi to Dtwn Springfield: Winter Retreat w/ Office

Holiday Home, Southampton

3 Mi to Dtwn Springfield: Winter Retreat w/ Office is a holiday home in Southampton, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About 3 Mi to Dtwn Springfield: Winter Retreat w/ Office

3 Mi to Dtwn Springfield: Winter Retreat w/ Office is a holiday home in Southampton, with 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 cancellation, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,697.

From$153/night
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Cozy 2-bedroom apartment Near Six Flags & Attractions - Southampton, MA

Cozy 2-bedroom apartment Near Six Flags & Attractions

Apartment, Southampton

Cozy 2-bedroom apartment Near Six Flags & Attractions is a apartment in Southampton, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 2-bedroom apartment Near Six Flags & Attractions

Cozy 2-bedroom apartment Near Six Flags & Attractions is a apartment in Southampton, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,150.

From$164/night
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Chic & Serene 4 Bed Apt w/ Wi-Fi - Southampton, MA

Chic & Serene 4 Bed Apt w/ Wi-Fi

Apartment, Southampton

Chic & Serene 4 Bed Apt w/ Wi-Fi is a apartment in Southampton, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Chic & Serene 4 Bed Apt w/ Wi-Fi

Chic & Serene 4 Bed Apt w/ Wi-Fi is a apartment in Southampton, 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 $1,186.

From$169/night
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2 Mi to Downtown: Springfield Apt w/ Balcony! - Southampton, MA

2 Mi to Downtown: Springfield Apt w/ Balcony!

Apartment, Southampton

2 Mi to Downtown: Springfield Apt w/ Balcony! is a apartment in Southampton, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 Mi to Downtown: Springfield Apt w/ Balcony!

2 Mi to Downtown: Springfield Apt w/ Balcony! is a apartment in Southampton, with 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, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,780.

From$177/night
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Vacation rentals with parking in Southampton, MA

Find vacation rentals that make arriving by car easier.

3 Mi to Dtwn Springfield: Winter Retreat w/ Office - Southampton, MA

3 Mi to Dtwn Springfield: Winter Retreat w/ Office

Holiday Home, Southampton

3 Mi to Dtwn Springfield: Winter Retreat w/ Office is a holiday home in Southampton, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About 3 Mi to Dtwn Springfield: Winter Retreat w/ Office

3 Mi to Dtwn Springfield: Winter Retreat w/ Office is a holiday home in Southampton, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,415.

From$202/night
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2bedrroom Mins from MGM, Downtown springfield, hospitals - Southampton, MA

2bedrroom Mins from MGM, Downtown springfield, hospitals

Apartment, Southampton

2bedrroom Mins from MGM, Downtown springfield, hospitals is a apartment in Southampton, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 2bedrroom Mins from MGM, Downtown springfield, hospitals

2bedrroom Mins from MGM, Downtown springfield, hospitals is a apartment in Southampton, 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 $1,443.

From$206/night
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2 Mi to Downtown: Springfield Apt w/ Balcony! - Southampton, MA

2 Mi to Downtown: Springfield Apt w/ Balcony!

Apartment, Southampton

2 Mi to Downtown: Springfield Apt w/ Balcony! is a apartment in Southampton, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About 2 Mi to Downtown: Springfield Apt w/ Balcony!

2 Mi to Downtown: Springfield Apt w/ Balcony! is a apartment in Southampton, with outdoor 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,491.

From$213/night
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Historic Huntington Home - Walk to Westfield River - Southampton, MA

Historic Huntington Home - Walk to Westfield River

Holiday Home, Southampton

Historic Huntington Home - Walk to Westfield River is a holiday home in Southampton, with parking. 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 holiday home in Southampton, 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, paid parking, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,126.

From$235/night
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Pet-friendly vacation rentals in Southampton, MA

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

Fearlessrose vacation Rental 89 - Southampton, MA

Fearlessrose vacation Rental 89

Guest House, Southampton

Fearlessrose vacation Rental 89 is a guest house in Southampton, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Fearlessrose vacation Rental 89

Fearlessrose vacation Rental 89 is a guest house in Southampton, 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 wifi, parking, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,907.

From$225/night
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Warm, charming 3BR house w fenced yard in quiet neighborhood close to everything - Southampton, MA

Warm, charming 3BR house w fenced yard in quiet neighborhood close to everything

Holiday Home, Southampton

Warm, charming 3BR house w fenced yard in quiet neighborhood close to everything is a holiday home in Southampton, with pet-friendly space, room for a group, and a quieter setting. This…

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About Warm, charming 3BR house w fenced yard in quiet neighborhood close to everything

Warm, charming 3BR house w fenced yard in quiet neighborhood close to everything is a holiday home in Southampton, with pet-friendly space, room for a group, 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,097.

From$300/night
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Private Retreat ranch house in South Amherst - Southampton, MA

Private Retreat ranch house in South Amherst

Holiday Home, Southampton

Private Retreat ranch house in South Amherst is a holiday home in Southampton, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Private Retreat ranch house in South Amherst

Private Retreat ranch house in South Amherst is a holiday home in Southampton, 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 $2,834.

From$405/night
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Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy - Southampton, MA

Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy

Holiday Home, Southampton

Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy is a holiday home in Southampton, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy

Beautifully Restored Federal Colonial. New pool,Large Deck, New Hot tub, privacy is a holiday home in Southampton, with pet-friendly space, pool access, and 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, pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,234.

From$462/night
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Vacation rentals with a kitchen in Southampton, MA

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

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself! - Southampton, MA

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Holiday Home, Southampton

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself! is a holiday home in Southampton, with kitchen access and a quieter setting. This stay gives travelers a…

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About Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself! is a holiday home in Southampton, with 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 wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,601.

From$229/night
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3-bedroom house in perfect Springfield with WiFi, AC - Southampton, MA

3-bedroom house in perfect Springfield with WiFi, AC

Holiday Home, Southampton

3-bedroom house in perfect Springfield with WiFi, AC is a holiday home in Southampton, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 3-bedroom house in perfect Springfield with WiFi, AC

3-bedroom house in perfect Springfield with WiFi, AC is a holiday home in Southampton, 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 $1,620.

From$231/night
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1 Mi to MGM Springfield: Cozy Winter Duplex! - Southampton, MA

1 Mi to MGM Springfield: Cozy Winter Duplex!

Apartment, Southampton

1 Mi to MGM Springfield: Cozy Winter Duplex! is a apartment in Southampton, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About 1 Mi to MGM Springfield: Cozy Winter Duplex!

1 Mi to MGM Springfield: Cozy Winter Duplex! is a apartment in Southampton, 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 $2,244.

From$233/night
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Historic Huntington Home - Walk to Westfield River - Southampton, MA

Historic Huntington Home - Walk to Westfield River

Holiday Home, Southampton

Historic Huntington Home - Walk to Westfield River is a holiday home in Southampton, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River is a holiday home in Southampton, 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 $1,912.

From$273/night
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Family-friendly vacation rentals in Southampton, MA

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

3 Mi to Dtwn Springfield: Winter Retreat w/ Office - Southampton, MA

3 Mi to Dtwn Springfield: Winter Retreat w/ Office

Cottage, Southampton

3 Mi to Dtwn Springfield: Winter Retreat w/ Office is a cottage in Southampton, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About 3 Mi to Dtwn Springfield: Winter Retreat w/ Office

3 Mi to Dtwn Springfield: Winter Retreat w/ Office is a cottage in Southampton, with parking, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,763.

From$187/night
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Fearlessrose vacation Rental 89 - Southampton, MA

Fearlessrose vacation Rental 89

B & B, Southampton

Fearlessrose vacation Rental 89 is a b & b in Southampton, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Fearlessrose vacation Rental 89

Fearlessrose vacation Rental 89 is a b & b in Southampton, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,728.

From$203/night
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Big farmhouse in the foothills of the Berkshires - Southampton, MA

Big farmhouse in the foothills of the Berkshires

Holiday Home, Southampton

Big farmhouse in the foothills of the Berkshires is a holiday home in Southampton, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires is a holiday home in Southampton, 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 $1,582.

From$226/night
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Historic Huntington Home - Walk to Westfield River - Southampton, MA

Historic Huntington Home - Walk to Westfield River

Cottage, Southampton

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

Read more

About Historic Huntington Home - Walk to Westfield River

Historic Huntington Home - Walk to Westfield River is a cottage in Southampton, 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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