Vacation rentals in Southborough, MA

31 available vacation rental offers

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Best vacation rentals and Airbnb offers in Southborough, MA

The Inn on the Horse Farm - Southborough, MA

The Inn on the Horse Farm

Guest House, Southborough

The Inn on the Horse Farm is a guest house in Southborough, 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 Inn on the Horse Farm

The Inn on the Horse Farm is a guest house in Southborough, 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, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,028.

From$131/night
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Cozy 1BR waterfront apartment with a 1st floor feel in Worcester, MA. - Southborough, MA

Cozy 1BR waterfront apartment with a 1st floor feel in Worcester, MA.

Apartment, Southborough

Cozy 1BR waterfront apartment with a 1st floor feel in Worcester, MA. is a apartment in Southborough, with pet-friendly space, easy beach access, and room for a group. This stay gives…

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About Cozy 1BR waterfront apartment with a 1st floor feel in Worcester, MA.

Cozy 1BR waterfront apartment with a 1st floor feel in Worcester, MA. is a apartment in Southborough, with pet-friendly space, easy beach 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,299.

From$186/night
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Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku. - Southborough, MA

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Holiday Home, Southborough

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku. is a holiday home in Southborough, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku.

Beautiful & Cozy 2 BR/ 2Beds/ Netflix/Alexa/Roku. is a holiday home in Southborough, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,389.

From$198/night
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Beautiful 2 Bedrooms with 2 Beds in Shrewsbury - Southborough, MA

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Holiday Home, Southborough

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury is a holiday home in Southborough, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful 2 Bedrooms with 2 Beds in Shrewsbury

Beautiful 2 Bedrooms with 2 Beds in Shrewsbury is a holiday home in Southborough, 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 $1,462.

From$209/night
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Vacation rentals with parking in Southborough, MA

Find vacation rentals that make arriving by car easier.

One Bedroom Apartment with Separate Bunk Bed Area - Southborough, MA

One Bedroom Apartment with Separate Bunk Bed Area

Apartment, Southborough

One Bedroom Apartment with Separate Bunk Bed Area is a apartment in Southborough, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About One Bedroom Apartment with Separate Bunk Bed Area

One Bedroom Apartment with Separate Bunk Bed Area is a apartment in Southborough, 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 $1,843.

From$263/night
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Guest Cabin on Quiet Estate 60km to Gillette - Southborough, MA

Guest Cabin on Quiet Estate 60km to Gillette

Cabin, Southborough

Guest Cabin on Quiet Estate 60km to Gillette is a cabin in Southborough, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Guest Cabin on Quiet Estate 60km to Gillette

Guest Cabin on Quiet Estate 60km to Gillette is a cabin in Southborough, 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 $2,649.

From$378/night
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totally remodeled house with fitness room, close to Boston and Worcester - Southborough, MA

totally remodeled house with fitness room, close to Boston and Worcester

Holiday Home, Southborough

totally remodeled house with fitness room, close to Boston and Worcester is a holiday home in Southborough, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About totally remodeled house with fitness room, close to Boston and Worcester

totally remodeled house with fitness room, close to Boston and Worcester is a holiday home in Southborough, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,675.

From$382/night
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Serene 4-bedroom Home in a Safe Town - Southborough, MA

Serene 4-bedroom Home in a Safe Town

Holiday Home, Southborough

Serene 4-bedroom Home in a Safe Town is a holiday home in Southborough, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Serene 4-bedroom Home in a Safe Town

Serene 4-bedroom Home in a Safe Town is a holiday home in Southborough, 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: kitchen, with kitchen, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,169.

From$453/night
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Pet-friendly vacation rentals in Southborough, MA

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

Jamaica Plain Condo - Southborough, MA

Jamaica Plain Condo

Holiday Home, Southborough

Jamaica Plain Condo is a holiday home in Southborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Jamaica Plain Condo

Jamaica Plain Condo is a holiday home in Southborough, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,088.

From$441/night
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Gorgeous MCM Deck House Near Gillette Stadium! - Southborough, MA

Gorgeous MCM Deck House Near Gillette Stadium!

Holiday Home, Southborough

Gorgeous MCM Deck House Near Gillette Stadium! is a holiday home in Southborough, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Gorgeous MCM Deck House Near Gillette Stadium!

Gorgeous MCM Deck House Near Gillette Stadium! is a holiday home in Southborough, 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,336.

From$477/night
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Spacious 4 bedroom home with large yard - Southborough, MA

Spacious 4 bedroom home with large yard

Holiday Home, Southborough

Spacious 4 bedroom home with large yard is a holiday home in Southborough, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Spacious 4 bedroom home with large yard

Spacious 4 bedroom home with large yard is a holiday home in Southborough, 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 $3,405.

From$486/night
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Charming home on Lake Quinsigamond! - Southborough, MA

Charming home on Lake Quinsigamond!

Holiday Home, Southborough

Charming home on Lake Quinsigamond! is a holiday home in Southborough, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming home on Lake Quinsigamond!

Charming home on Lake Quinsigamond! is a holiday home in Southborough, 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 $3,782.

From$540/night
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Vacation rentals with a kitchen in Southborough, MA

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

Newly updated/furnished 3 bedrooms house - Southborough, MA

Newly updated/furnished 3 bedrooms house

Holiday Home, Southborough

Newly updated/furnished 3 bedrooms house is a holiday home in Southborough, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Newly updated/furnished 3 bedrooms house

Newly updated/furnished 3 bedrooms house is a holiday home in Southborough, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,765.

From$252/night
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Sakura House: Spacious 4BR w/ Gym & Premium Design - Southborough, MA

Sakura House: Spacious 4BR w/ Gym & Premium Design

Condo, Southborough

Sakura House: Spacious 4BR w/ Gym & Premium Design is a condo in Southborough, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Sakura House: Spacious 4BR w/ Gym & Premium Design

Sakura House: Spacious 4BR w/ Gym & Premium Design is a condo in Southborough, 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: kitchen, with kitchen, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,664.

From$666/night
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18 Mi to Boston - Stylish Unit in Upscale Enclave! - Southborough, MA

18 Mi to Boston - Stylish Unit in Upscale Enclave!

Apartment, Southborough

18 Mi to Boston - Stylish Unit in Upscale Enclave! is a apartment in Southborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 18 Mi to Boston - Stylish Unit in Upscale Enclave!

18 Mi to Boston - Stylish Unit in Upscale Enclave! is a apartment in Southborough, 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 $4,928.

From$704/night
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Family-friendly vacation rentals in Southborough, MA

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

Cottage Suite \"B\" - Walk to Shops, Train, History - Southborough, MA

Cottage Suite \"B\" - Walk to Shops, Train, History

Apartment, Southborough

Cottage Suite \"B\" - Walk to Shops, Train, History is a apartment in Southborough, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cottage Suite \"B\" - Walk to Shops, Train, History

Cottage Suite \"B\" - Walk to Shops, Train, History is a apartment in Southborough, 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 $1,984.

From$283/night
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Stay at adorable mill house in walkable Maynard. Small but well-designed spaces. - Southborough, MA

Stay at adorable mill house in walkable Maynard. Small but well-designed spaces.

Holiday Home, Southborough

Stay at adorable mill house in walkable Maynard. Small but well-designed spaces. is a holiday home in Southborough, with parking and kitchen access. This stay gives travelers a comfortable…

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About Stay at adorable mill house in walkable Maynard. Small but well-designed spaces.

Stay at adorable mill house in walkable Maynard. Small but well-designed spaces. is a holiday home in Southborough, 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 $2,528.

From$361/night
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Gorgeous MCM Deck House Near Gillette Stadium! - Southborough, MA

Gorgeous MCM Deck House Near Gillette Stadium!

Cottage, Southborough

Gorgeous MCM Deck House Near Gillette Stadium! is a cottage in Southborough, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Gorgeous MCM Deck House Near Gillette Stadium!

Gorgeous MCM Deck House Near Gillette Stadium! is a cottage in Southborough, 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 $3,869.

From$479/night
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Charming Modern 3-bdrm house. Stroll to Lake Quinsigamond in Worcester - Southborough, MA

Charming Modern 3-bdrm house. Stroll to Lake Quinsigamond in Worcester

Holiday Home, Southborough

Charming Modern 3-bdrm house. Stroll to Lake Quinsigamond in Worcester is a holiday home in Southborough, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Charming Modern 3-bdrm house. Stroll to Lake Quinsigamond in Worcester

Charming Modern 3-bdrm house. Stroll to Lake Quinsigamond in Worcester is a holiday home in Southborough, 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, gym, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,088.

From$584/night
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Best vacation rentals and Airbnb offers in Southborough | sillystay