Vacation rentals in Roslindale, MA

193 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Roslindale, MA

Cozy basement/studio apartment with kitchenette and bathroom! - Roslindale, MA

Cozy basement/studio apartment with kitchenette and bathroom!

Apartment, Roslindale

Cozy basement/studio apartment with kitchenette and bathroom! is a apartment in Roslindale, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy basement/studio apartment with kitchenette and bathroom!

Cozy basement/studio apartment with kitchenette and bathroom! is a apartment in Roslindale, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,378.

From$134/night
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A One Room Studio in a Quiet & Convenient Location - Roslindale, MA

A One Room Studio in a Quiet & Convenient Location

Holiday Home, Roslindale

A One Room Studio in a Quiet & Convenient Location is a holiday home in Roslindale, 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 Roslindale, 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 $1,467.

From$147/night
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3 Mi to Franklin Park Zoo! Bright Residential Stay - Roslindale, MA

3 Mi to Franklin Park Zoo! Bright Residential Stay

Condo, Roslindale

3 Mi to Franklin Park Zoo! Bright Residential Stay is a condo in Roslindale, 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 Roslindale, 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 $1,928.

From$158/night
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3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt - Roslindale, MA

3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt

Apartment, Roslindale

3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt is a apartment in Roslindale, 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 Blue Hills Skiing & Hiking! Couple’s Apt

3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt is a apartment in Roslindale, 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 $1,564.

From$161/night
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Browse Vacation Rentals with a Pool in Roslindale, MA

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

Global Luxury Suites East Boston - Roslindale, MA

Global Luxury Suites East Boston

Apartment, Roslindale

Global Luxury Suites East Boston is a apartment in Roslindale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Global Luxury Suites East Boston

Global Luxury Suites East Boston is a apartment in Roslindale, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,032.

From$232/night
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Global Luxury Suites East Boston - Roslindale, MA

Global Luxury Suites East Boston

Apartment, Roslindale

Global Luxury Suites East Boston is a apartment in Roslindale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Global Luxury Suites East Boston

Global Luxury Suites East Boston is a apartment in Roslindale, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,032.

From$232/night
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Spacious vacation townhome unit with a pool - Roslindale, MA

Spacious vacation townhome unit with a pool

Holiday Home, Roslindale

Spacious vacation townhome unit with a pool is a holiday home in Roslindale, 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 Roslindale, 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 $2,965.

From$339/night
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Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! - Roslindale, MA

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

Holiday Home, Roslindale

Perfect World Cup Getaway – Close to Stadium & Pool, Grill & Gym included! is a holiday home in Roslindale, 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 Roslindale, 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 $4,598.

From$506/night
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Best Roslindale, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Private Room in a Grand House - Roslindale, MA

Private Room in a Grand House

Homestay, Roslindale

Private Room in a Grand House is a homestay in Roslindale, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Private Room in a Grand House

Private Room in a Grand House is a homestay in Roslindale, 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 $1,464.

From$179/night
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3 Mi to Blue Hills Skiing & Hiking! Couples Apt - Roslindale, MA

3 Mi to Blue Hills Skiing & Hiking! Couples Apt

Apartment, Roslindale

3 Mi to Blue Hills Skiing & Hiking! Couples Apt is a apartment in Roslindale, 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 Blue Hills Skiing & Hiking! Couples Apt

3 Mi to Blue Hills Skiing & Hiking! Couples Apt is a apartment in Roslindale, 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 $1,705.

From$222/night
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Lovey Spacious 2 Bedroom Apartment 15 min from Airport/Downtown - Roslindale, MA

Lovey Spacious 2 Bedroom Apartment 15 min from Airport/Downtown

Apartment, Roslindale

Lovey Spacious 2 Bedroom Apartment 15 min from Airport/Downtown is a apartment in Roslindale, with parking and room for a group. This stay gives travelers a comfortable base for exploring…

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About Lovey Spacious 2 Bedroom Apartment 15 min from Airport/Downtown

Lovey Spacious 2 Bedroom Apartment 15 min from Airport/Downtown is a apartment in Roslindale, 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: parking, free parking, ac, air conditioning, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,414.

From$232/night
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~*30min to Downtown*~ THE COSMOPOLITAN - Roslindale, MA

~*30min to Downtown*~ THE COSMOPOLITAN

Holiday Home, Roslindale

~*30min to Downtown*~ THE COSMOPOLITAN is a holiday home in Roslindale, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About ~*30min to Downtown*~ THE COSMOPOLITAN

~*30min to Downtown*~ THE COSMOPOLITAN is a holiday home in Roslindale, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,145.

From$248/night
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Best Pet-Friendly Vacation Rentals in Roslindale, MA

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

Boston's Best Vacation Home - Roslindale, MA

Boston's Best Vacation Home

Holiday Home, Roslindale

Boston's Best Vacation Home is a holiday home in Roslindale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Boston's Best Vacation Home

Boston's Best Vacation Home is a holiday home in Roslindale, 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 $2,538.

From$248/night
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Roslindale village condos - Roslindale, MA

Roslindale village condos

Apartment, Roslindale

Roslindale village condos is a apartment in Roslindale, 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 Roslindale, 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 $2,258.

From$257/night
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Roslindale village condos - Roslindale, MA

Roslindale village condos

Apartment, Roslindale

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

Read more

About Roslindale village condos

Roslindale village condos is a apartment in Roslindale, 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 $2,258.

From$257/night
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~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN - Roslindale, MA

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Holiday Home, Roslindale

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN is a holiday home in Roslindale, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About ~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN is a holiday home in Roslindale, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,366.

From$268/night
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Best Roslindale, MA vacation rentals with a kitchen

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

Charming 1BR Apt in Boston w/ ROKU TV! - Roslindale, MA

Charming 1BR Apt in Boston w/ ROKU TV!

Apartment, Roslindale

Charming 1BR Apt in Boston w/ ROKU TV! is a apartment in Roslindale, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming 1BR Apt in Boston w/ ROKU TV!

Charming 1BR Apt in Boston w/ ROKU TV! is a apartment in Roslindale, 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,147.

From$219/night
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Charming Victorian Furnished Home - Roslindale, MA

Charming Victorian Furnished Home

Apartment, Roslindale

Charming Victorian Furnished Home is a apartment in Roslindale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Victorian Furnished Home

Charming Victorian Furnished Home is a apartment in Roslindale, 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 $2,562.

From$272/night
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Boston Duplex w/ Foosball Table: 11 Mi to Downtown - Roslindale, MA

Boston Duplex w/ Foosball Table: 11 Mi to Downtown

Apartment, Roslindale

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

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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 Roslindale, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,432.

From$276/night
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Beautiful, private and tranquil 2 bedroom historic Boston carriage house. - Roslindale, MA

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

Holiday Home, Roslindale

Beautiful, private and tranquil 2 bedroom historic Boston carriage house. is a holiday home in Roslindale, 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 Roslindale, 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 $2,993.

From$296/night
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Our Favorite Family-Friendly Vacation Rentals in Roslindale, MA

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

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

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

Holiday Home, Roslindale

1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts is a holiday home in Roslindale, 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 Roslindale, 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 $2,390.

From$241/night
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Newly Renovated Open-Concept living space, close to Boston, plenty of parking - Roslindale, MA

Newly Renovated Open-Concept living space, close to Boston, plenty of parking

Holiday Home, Roslindale

Newly Renovated Open-Concept living space, close to Boston, plenty of parking is a holiday home in Roslindale, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Newly Renovated Open-Concept living space, close to Boston, plenty of parking

Newly Renovated Open-Concept living space, close to Boston, plenty of parking is a holiday home in Roslindale, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,630.

From$302/night
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The Enchanted Willow Boston Escape 3BDR/Free Parking/EV Charger/Family-friendly - Roslindale, MA

The Enchanted Willow Boston Escape 3BDR/Free Parking/EV Charger/Family-friendly

Apartment, Roslindale

The Enchanted Willow Boston Escape 3BDR/Free Parking/EV Charger/Family-friendly is a apartment in Roslindale, with parking and room for a group. This stay gives travelers a comfortable base…

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About The Enchanted Willow Boston Escape 3BDR/Free Parking/EV Charger/Family-friendly

The Enchanted Willow Boston Escape 3BDR/Free Parking/EV Charger/Family-friendly is a apartment in Roslindale, 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, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,820.

From$311/night
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Family-Friendly 3BR Vacation Home w/ Free Parking Near Franklin Park 558/1 - Roslindale, MA

Family-Friendly 3BR Vacation Home w/ Free Parking Near Franklin Park 558/1

Apartment, Roslindale

Family-Friendly 3BR Vacation Home w/ Free Parking Near Franklin Park 558/1 is a apartment in Roslindale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Family-Friendly 3BR Vacation Home w/ Free Parking Near Franklin Park 558/1

Family-Friendly 3BR Vacation Home w/ Free Parking Near Franklin Park 558/1 is a apartment in Roslindale, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,220.

From$340/night
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