Vacation rentals in Wellesley, MA

108 available vacation rental offers

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Best vacation rentals and Airbnb offers in Wellesley, MA

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

154 Quite & Bright & Spacious Apt in Brighton

Homestay, Wellesley

154 Quite & Bright & Spacious Apt in Brighton is a homestay in Wellesley, 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 Wellesley, 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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5BR 2BH Bright & Spacious Apt in Brighton - Wellesley, MA

5BR 2BH Bright & Spacious Apt in Brighton

Apartment, Wellesley

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Wellesley, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 5BR 2BH Bright & Spacious Apt in Brighton

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Wellesley, 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 $1,337.

From$118/night
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5BR 2BH Bright & Spacious Apt in Brighton - Wellesley, MA

5BR 2BH Bright & Spacious Apt in Brighton

Apartment, Wellesley

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Wellesley, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 5BR 2BH Bright & Spacious Apt in Brighton

5BR 2BH Bright & Spacious Apt in Brighton is a apartment in Wellesley, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$118/night
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Cozy Up in 5BR Apt Near Charming Oak Square - Wellesley, MA

Cozy Up in 5BR Apt Near Charming Oak Square

Apartment, Wellesley

Cozy Up in 5BR Apt Near Charming Oak Square is a apartment in Wellesley, 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 Wellesley, 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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Vacation rentals with a pool in Wellesley, 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 - Wellesley, MA

Spacious vacation townhome unit with a pool

Holiday Home, Wellesley

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

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About Spacious vacation townhome unit with a pool

Spacious vacation townhome unit with a pool is a holiday home in Wellesley, 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 $2,696.

From$385/night
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Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! - Wellesley, MA

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

Holiday Home, Wellesley

Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! is a holiday home in Wellesley, 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 Wellesley, 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. - Wellesley, MA

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

Holiday Home, Wellesley

Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym. is a holiday home in Wellesley, 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 Wellesley, 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. - Wellesley, MA

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

Holiday Home, Wellesley

Gorgeous, Peaceful Sanctuary on lake minutes from Boston & all local colleges. is a holiday home in Wellesley, 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 Wellesley, 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 Wellesley, MA

Find vacation rentals that make arriving by car easier.

Beacon Inn 1750 - Wellesley, MA

Beacon Inn 1750

Guest House, Wellesley

Beacon Inn 1750 is a guest house in Wellesley, 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 Wellesley, 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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3 Mi to Franklin Park Zoo! Bright Residential Stay - Wellesley, MA

3 Mi to Franklin Park Zoo! Bright Residential Stay

Condo, Wellesley

3 Mi to Franklin Park Zoo! Bright Residential Stay is a condo in Wellesley, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 3 Mi to Franklin Park Zoo! Bright Residential Stay

3 Mi to Franklin Park Zoo! Bright Residential Stay is a condo in Wellesley, 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 $1,644.

From$235/night
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Boston Duplex w/ Foosball Table: 11 Mi to Downtown - Wellesley, MA

Boston Duplex w/ Foosball Table: 11 Mi to Downtown

Apartment, Wellesley

Boston Duplex w/ Foosball Table: 11 Mi to Downtown is a apartment in Wellesley, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Boston Duplex w/ Foosball Table: 11 Mi to Downtown

Boston Duplex w/ Foosball Table: 11 Mi to Downtown is a apartment in Wellesley, 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 heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,403.

From$239/night
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Beacon Inn 1750 - Wellesley, MA

Beacon Inn 1750

B & B, Wellesley

Beacon Inn 1750 is a b & b in Wellesley, 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 b & b in Wellesley, 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 Wellesley, MA

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

A One Room Studio in a Quiet & Convenient Location - Wellesley, MA

A One Room Studio in a Quiet & Convenient Location

Holiday Home, Wellesley

A One Room Studio in a Quiet & Convenient Location is a holiday home in Wellesley, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About A One Room Studio in a Quiet & Convenient Location

A One Room Studio in a Quiet & Convenient Location is a holiday home in Wellesley, 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 $1,276.

From$182/night
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Roslindale village condos - Wellesley, MA

Roslindale village condos

Apartment, Wellesley

Roslindale village condos is a apartment in Wellesley, 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 Wellesley, 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 $2,415.

From$276/night
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Roslindale village condos - Wellesley, MA

Roslindale village condos

Apartment, Wellesley

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

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About Roslindale village condos

Roslindale village condos is a apartment in Wellesley, 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 $2,415.

From$276/night
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Quaint apartment in charming Framingham, 5 Min to FSU - Wellesley, MA

Quaint apartment in charming Framingham, 5 Min to FSU

Apartment, Wellesley

Quaint apartment in charming Framingham, 5 Min to FSU is a apartment in Wellesley, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Quaint apartment in charming Framingham, 5 Min to FSU

Quaint apartment in charming Framingham, 5 Min to FSU is a apartment in Wellesley, 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 $1,961.

From$280/night
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Vacation rentals with a kitchen in Wellesley, MA

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

Furnished Luxury Apartment Next to Harvard Stadium - Wellesley, MA

Furnished Luxury Apartment Next to Harvard Stadium

Apartment, Wellesley

Furnished Luxury Apartment Next to Harvard Stadium is a apartment in Wellesley, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Furnished Luxury Apartment Next to Harvard Stadium

Furnished Luxury Apartment Next to Harvard Stadium is a apartment in Wellesley, 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,346.

From$276/night
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Renovated 3rd-Floor Retreat | 3 Beds | Roslindale Village - Wellesley, MA

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

Holiday Home, Wellesley

Renovated 3rd-Floor Retreat · 3 Beds · Roslindale Village is a holiday home in Wellesley, 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 Wellesley, 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 $1,975.

From$282/night
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Charming Townhouse 12 minutes to Boston - Wellesley, MA

Charming Townhouse 12 minutes to Boston

Apartment, Wellesley

Charming Townhouse 12 minutes to Boston is a apartment in Wellesley, 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 Wellesley, 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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Remodeled Townhouse close to Boston - Wellesley, MA

Remodeled Townhouse close to Boston

Holiday Home, Wellesley

Remodeled Townhouse close to Boston is a holiday home in Wellesley, 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 Wellesley, 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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Family-friendly vacation rentals in Wellesley, MA

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

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

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

Apartment, Wellesley

Cottage Suite \"B\" - Walk to Shops, Train, History is a apartment in Wellesley, 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 Wellesley, 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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1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts - Wellesley, MA

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts

Holiday Home, Wellesley

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in Wellesley, with parking, kitchen access, and room for a group. This stay gives travelers…

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About 1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in Wellesley, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,094.

From$299/night
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Cozy Cambridge Cottage Retreat Near Harvard - Wellesley, MA

Cozy Cambridge Cottage Retreat Near Harvard

Apartment, Wellesley

Cozy Cambridge Cottage Retreat Near Harvard is a apartment in Wellesley, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Cambridge Cottage Retreat Near Harvard

Cozy Cambridge Cottage Retreat Near Harvard is a apartment in Wellesley, with pet-friendly space 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 $2,399.

From$343/night
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Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley - Wellesley, MA

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

Holiday Home, Wellesley

Entire Nice Quiet Home, Near All Colleges, Very Convenience in Central Wellesley is a holiday home in Wellesley, 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 Wellesley, 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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