Vacation rentals in Sherborn, MA

60 available vacation rental offers

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Best vacation rentals and Airbnb offers in Sherborn, MA

154 Quite & Bright & Spacious Apt in Brighton - Sherborn, MA

154 Quite & Bright & Spacious Apt in Brighton

Homestay, Sherborn

154 Quite & Bright & Spacious Apt in Brighton is a homestay in Sherborn, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About 154 Quite & Bright & Spacious Apt in Brighton

154 Quite & Bright & Spacious Apt in Brighton is a homestay in Sherborn, 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: parking, free parking, lang::en, can speak english, and non smoking::all.

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

From$92/night
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Cozy Up in 5BR Apt Near Charming Oak Square - Sherborn, MA

Cozy Up in 5BR Apt Near Charming Oak Square

Apartment, Sherborn

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Sherborn, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Up in 5BR Apt Near Charming Oak Square

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Sherborn, 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 wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,406.

From$125/night
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Cozy Up in 5BR Apt Near Charming Oak Square - Sherborn, MA

Cozy Up in 5BR Apt Near Charming Oak Square

Apartment, Sherborn

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Sherborn, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Cozy Up in 5BR Apt Near Charming Oak Square

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Sherborn, with 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 wifi, ac, air conditioning, tv, and cctv inside.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,406.

From$125/night
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The Inn on the Horse Farm - Sherborn, MA

The Inn on the Horse Farm

Guest House, Sherborn

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

The Inn on the Horse Farm is a guest house in Sherborn, 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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Vacation rentals with a pool in Sherborn, MA

Add a pool to the search when you want an easy place to cool off between outings.

Spacious vacation townhome unit with a pool - Sherborn, MA

Spacious vacation townhome unit with a pool

Holiday Home, Sherborn

Spacious vacation townhome unit with a pool is a holiday home in Sherborn, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Spacious vacation townhome unit with a pool

Spacious vacation townhome unit with a pool is a holiday home in Sherborn, with pool access 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,862.

From$409/night
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Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! - Sherborn, MA

Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included!

Holiday Home, Sherborn

Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! is a holiday home in Sherborn, with pool access. This stay gives travelers a comfortable base for exploring the…

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About Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included!

Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! is a holiday home in Sherborn, with pool 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, pool, hot tub, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,116.

From$588/night
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Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym. - Sherborn, MA

Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym.

Holiday Home, Sherborn

Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym. is a holiday home in Sherborn, with pool access, kitchen access, and room for a group. This stay gives…

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About Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym.

Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym. is a holiday home in Sherborn, with pool access, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,903.

From$1,700/night
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Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges. - Sherborn, MA

Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges.

Holiday Home, Sherborn

Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges. is a holiday home in Sherborn, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges.

Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges. is a holiday home in Sherborn, with pool access 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $32,938.

From$4,705/night
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Vacation rentals with parking in Sherborn, MA

Find vacation rentals that make arriving by car easier.

Beacon Inn 1750 - Sherborn, MA

Beacon Inn 1750

Guest House, Sherborn

Beacon Inn 1750 is a guest house in Sherborn, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Beacon Inn 1750

Beacon Inn 1750 is a guest house in Sherborn, 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, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,490.

From$191/night
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Experience Classic Charm in a Cozy 115-Year-Old Colonial - Sherborn, MA

Experience Classic Charm in a Cozy 115-Year-Old Colonial

Apartment, Sherborn

Experience Classic Charm in a Cozy 115-Year-Old Colonial is a apartment in Sherborn, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Experience Classic Charm in a Cozy 115-Year-Old Colonial

Experience Classic Charm in a Cozy 115-Year-Old Colonial is a apartment in Sherborn, 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 $1,993.

From$285/night
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Remodeled Townhouse close to Boston - Sherborn, MA

Remodeled Townhouse close to Boston

Holiday Home, Sherborn

Remodeled Townhouse close to Boston is a holiday home in Sherborn, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Remodeled Townhouse close to Boston

Remodeled Townhouse close to Boston is a holiday home in Sherborn, 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 $2,356.

From$337/night
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Beacon Inn 1750 - Sherborn, MA

Beacon Inn 1750

B & B, Sherborn

Beacon Inn 1750 is a b & b in Sherborn, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Beacon Inn 1750

Beacon Inn 1750 is a b & b in Sherborn, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,490.

From$191/night
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Pet-friendly vacation rentals in Sherborn, MA

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

Roslindale village condos - Sherborn, MA

Roslindale village condos

Apartment, Sherborn

Roslindale village condos is a apartment in Sherborn, 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 Roslindale village condos

Roslindale village condos is a apartment in Sherborn, 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 $2,237.

From$254/night
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Roslindale village condos - Sherborn, MA

Roslindale village condos

Apartment, Sherborn

Roslindale village condos is a apartment in Sherborn, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Roslindale village condos

Roslindale village condos is a apartment in Sherborn, 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 $2,237.

From$254/night
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Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village - Sherborn, MA

Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village

Holiday Home, Sherborn

Renovated 3rd-Floor Retreat · 3 Beds · Roslindale Village is a holiday home in Sherborn, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village

Renovated 3rd-Floor Retreat · 3 Beds · Roslindale Village is a holiday home in Sherborn, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,835.

From$262/night
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Gorgeous MCM Deck House Near Gillette Stadium! - Sherborn, MA

Gorgeous MCM Deck House Near Gillette Stadium!

Holiday Home, Sherborn

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

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About Gorgeous MCM Deck House Near Gillette Stadium!

Gorgeous MCM Deck House Near Gillette Stadium! is a holiday home in Sherborn, 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 $3,337.

From$477/night
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Vacation rentals with a kitchen in Sherborn, MA

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

Charming Townhouse 12 minutes to Boston - Sherborn, MA

Charming Townhouse 12 minutes to Boston

Apartment, Sherborn

Charming Townhouse 12 minutes to Boston is a apartment in Sherborn, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Townhouse 12 minutes to Boston

Charming Townhouse 12 minutes to Boston is a apartment in Sherborn, 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 $2,356.

From$337/night
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Beautiful, private and tranquil 2 bedroom historic Boston carriage house. - Sherborn, MA

Beautiful, private and tranquil 2 bedroom historic Boston carriage house.

Holiday Home, Sherborn

Beautiful, private and tranquil 2 bedroom historic Boston carriage house. is a holiday home in Sherborn, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Beautiful, private and tranquil 2 bedroom historic Boston carriage house.

Beautiful, private and tranquil 2 bedroom historic Boston carriage house. is a holiday home in Sherborn, 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, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,604.

From$372/night
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Serene 4-bedroom Home in a Safe Town - Sherborn, MA

Serene 4-bedroom Home in a Safe Town

Holiday Home, Sherborn

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

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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 Sherborn, 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 $3,133.

From$448/night
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Spacious 4 bedroom home with large yard - Sherborn, MA

Spacious 4 bedroom home with large yard

Holiday Home, Sherborn

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

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About Spacious 4 bedroom home with large yard

Spacious 4 bedroom home with large yard is a holiday home in Sherborn, 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 $3,377.

From$482/night
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Family-friendly vacation rentals in Sherborn, MA

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

4BR Family Home • Parking • Near Boston • Gillette Stadium • FIFA World Cup - Sherborn, MA

4BR Family Home • Parking • Near Boston • Gillette Stadium • FIFA World Cup

Holiday Home, Sherborn

4BR Family Home · Parking · Near Boston · Gillette Stadium · FIFA World Cup is a holiday home in Sherborn, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 4BR Family Home • Parking • Near Boston • Gillette Stadium • FIFA World Cup

4BR Family Home · Parking · Near Boston · Gillette Stadium · FIFA World Cup is a holiday home in Sherborn, 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 $2,830.

From$404/night
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Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley - Sherborn, MA

Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley

Holiday Home, Sherborn

Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley is a holiday home in Sherborn, with kitchen access and a quieter setting. This stay gives travelers a…

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About Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley

Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley is a holiday home in Sherborn, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,007.

From$430/night
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Gorgeous MCM Deck House Near Gillette Stadium! - Sherborn, MA

Gorgeous MCM Deck House Near Gillette Stadium!

Cottage, Sherborn

Gorgeous MCM Deck House Near Gillette Stadium! is a cottage in Sherborn, 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 Sherborn, 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 $3,873.

From$480/night
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Charming 2-bedroom Guest House in Dedham on Private Estate - Sherborn, MA

Charming 2-bedroom Guest House in Dedham on Private Estate

Cottage, Sherborn

Charming 2-bedroom Guest House in Dedham on Private Estate is a cottage in Sherborn, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 2-bedroom Guest House in Dedham on Private Estate

Charming 2-bedroom Guest House in Dedham on Private Estate is a cottage in Sherborn, with pet-friendly space 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 $3,689.

From$527/night
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