Vacation rentals in Winthrop, MA

Best Vacation rentals and Airbnb offers in Winthrop, MA

Boston Queen Bedroom

Apartment, Winthrop

Boston Queen Bedroom is a apartment in Winthrop, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Boston Queen Bedroom

Boston Queen Bedroom is a apartment in Winthrop, 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 cancellation, free wifi, ac, air conditioning, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,073.

From$134/night

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Airport room 1

Homestay, Winthrop

Airport room 1 is a homestay in Winthrop, 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 Airport room 1

Airport room 1 is a homestay in Winthrop, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,031.

From$122/night

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1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena.

Apartment, Winthrop

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena. is a apartment in Winthrop, with easy beach access and room for a group. This stay gives travelers a…

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About 1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena.

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena. is a apartment in Winthrop, with 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: free cancellation, internet, non smoking, and shower.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,097.

From$157/night

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Ocean Spray Inn

Homestay, Winthrop

Ocean Spray Inn is a homestay in Winthrop, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Ocean Spray Inn

Ocean Spray Inn is a homestay in Winthrop, with pet-friendly space, easy beach 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,539.

From$180/night

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Best Winthrop, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Boston Monadnock Properties

Homestay, Winthrop

Boston Monadnock Properties is a homestay in Winthrop, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Boston Monadnock Properties

Boston Monadnock Properties is a homestay in Winthrop, 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 $848.

From$86/night

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Boston Monadnock Properties

Homestay, Winthrop

Boston Monadnock Properties is a homestay in Winthrop, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Boston Monadnock Properties

Boston Monadnock Properties is a homestay in Winthrop, 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 wifi, kitchen, with kitchen, parking, and parking nearby.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $848.

From$86/night

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Convenient 2 bed Apt in Everett a Short Walk to Encore

Apartment, Winthrop

Convenient 2 bed Apt in Everett a Short Walk to Encore is a apartment in Winthrop, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Convenient 2 bed Apt in Everett a Short Walk to Encore

Convenient 2 bed Apt in Everett a Short Walk to Encore is a apartment in Winthrop, 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 $1,686.

From$241/night

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Oceanfront Escape Near Boston - Steps to Sand

Apartment, Winthrop

Oceanfront Escape Near Boston - Steps to Sand is a apartment in Winthrop, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Oceanfront Escape Near Boston - Steps to Sand

Oceanfront Escape Near Boston - Steps to Sand is a apartment in Winthrop, with easy beach access, 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 $2,251.

From$322/night

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Best Pet-Friendly Vacation Rentals in Winthrop, MA

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

Charming New England style apartment 6 mi to downtown Boston, 4 mi to airport

Apartment, Winthrop

Charming New England style apartment 6 mi to downtown Boston, 4 mi to airport is a apartment in Winthrop, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Charming New England style apartment 6 mi to downtown Boston, 4 mi to airport

Charming New England style apartment 6 mi to downtown Boston, 4 mi to airport is a apartment in Winthrop, 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 $1,803.

From$258/night

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Sterling 1BR at Everett | Pool & Gym

Apartment, Winthrop

Sterling 1BR at Everett · Pool & Gym is a apartment in Winthrop, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Sterling 1BR at Everett | Pool & Gym

Sterling 1BR at Everett · Pool & Gym is a apartment in Winthrop, with pet-friendly space, pool 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,982.

From$283/night

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Unit 22 Luxurious 1BR Apartment Long-term stays

Apartment, Winthrop

Unit 22 Luxurious 1BR Apartment Long-term stays is a apartment in Winthrop, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Unit 22 Luxurious 1BR Apartment Long-term stays

Unit 22 Luxurious 1BR Apartment Long-term stays is a apartment in Winthrop, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,042.

From$292/night

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Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Condo, Winthrop

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC is a condo in Winthrop, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming 2-bedroom condo in delightful Chelsea with WiFi, AC

Charming 2-bedroom condo in delightful Chelsea with WiFi, AC is a condo in Winthrop, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,335.

From$334/night

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Best Winthrop, MA vacation rentals with a kitchen

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

Coastal Stay 2 Modern Ocean View Apartments Walk to Beach 4 Free Parking Spaces

Apartment, Winthrop

Coastal Stay 2 Modern Ocean View Apartments Walk to Beach 4 Free Parking Spaces is a apartment in Winthrop, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Coastal Stay 2 Modern Ocean View Apartments Walk to Beach 4 Free Parking Spaces

Coastal Stay 2 Modern Ocean View Apartments Walk to Beach 4 Free Parking Spaces is a apartment in Winthrop, with easy beach access, 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 $2,688.

From$310/night

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Furnished Luxury Apartment Close to Boston

Apartment, Winthrop

Furnished Luxury Apartment Close to Boston is a apartment in Winthrop, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Furnished Luxury Apartment Close to Boston

Furnished Luxury Apartment Close to Boston is a apartment in Winthrop, 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 $1,578.

From$208/night

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Luxury 1BR Close to Boston h26a

Apartment, Winthrop

Luxury 1BR Close to Boston h26a is a apartment in Winthrop, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury 1BR Close to Boston h26a

Luxury 1BR Close to Boston h26a is a apartment in Winthrop, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,772.

From$253/night

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Luxury 1BR near Boston mgq3

Apartment, Winthrop

Luxury 1BR near Boston mgq3 is a apartment in Winthrop, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury 1BR near Boston mgq3

Luxury 1BR near Boston mgq3 is a apartment in Winthrop, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,772.

From$253/night

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Our Favorite Family-Friendly Vacation Rentals in Winthrop, MA

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

Charming Colonial Two Bedroom Basement Apartment

Holiday Home, Winthrop

Charming Colonial Two Bedroom Basement Apartment is a holiday home in Winthrop, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Charming Colonial Two Bedroom Basement Apartment

Charming Colonial Two Bedroom Basement Apartment is a holiday home in Winthrop, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,710.

From$244/night

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Peaceful, bright family home near Hospitals, Encore casino, T station.

Apartment, Winthrop

Peaceful, bright family home near Hospitals, Encore casino, T station. is a apartment in Winthrop, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Peaceful, bright family home near Hospitals, Encore casino, T station.

Peaceful, bright family home near Hospitals, Encore casino, T station. is a apartment in Winthrop, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,017.

From$288/night

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Quiet Grand piano Apt near T station towards Boston, TD Garden, and Hospitals.

Holiday Home, Winthrop

Quiet Grand piano Apt near T station towards Boston, TD Garden, and Hospitals. is a holiday home in Winthrop, with kitchen access and a quieter setting. This stay gives travelers a…

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About Quiet Grand piano Apt near T station towards Boston, TD Garden, and Hospitals.

Quiet Grand piano Apt near T station towards Boston, TD Garden, and Hospitals. is a holiday home in Winthrop, 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 cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,073.

From$296/night

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Bright 2BR by Boston Waterfront

Apartment, Winthrop

Bright 2BR by Boston Waterfront is a apartment in Winthrop, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Bright 2BR by Boston Waterfront

Bright 2BR by Boston Waterfront is a apartment in Winthrop, with easy beach 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: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,176.

From$311/night

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