Vacation rentals in Thimble Island, MA

200 available vacation rental offers

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Best vacation rentals and Airbnb offers in Thimble Island, MA

Homestay Near Downtown Boston - Thimble Island, MA

Homestay Near Downtown Boston

B & B, Thimble Island

Homestay Near Downtown Boston is a b & b in Thimble Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Homestay Near Downtown Boston

Homestay Near Downtown Boston is a b & b in Thimble Island, 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 breakfast, free wifi, kitchen, with kitchen, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $797.

From$99/night
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HomeStay in Harvest Street - Thimble Island, MA

HomeStay in Harvest Street

B & B, Thimble Island

HomeStay in Harvest Street is a b & b in Thimble Island, 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 HomeStay in Harvest Street

HomeStay in Harvest Street is a b & b in Thimble Island, 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $863.

From$104/night
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Quarters on DOT by Short Term Rentals Boston - Thimble Island, MA

Quarters on DOT by Short Term Rentals Boston

Apartment, Thimble Island

Quarters on DOT by Short Term Rentals Boston is a apartment in Thimble Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Quarters on DOT by Short Term Rentals Boston

Quarters on DOT by Short Term Rentals Boston is a apartment in Thimble Island, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $924.

From$107/night
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Quarters on DOT by Thatch - Thimble Island, MA

Quarters on DOT by Thatch

Apartment, Thimble Island

Quarters on DOT by Thatch is a apartment in Thimble Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Quarters on DOT by Thatch

Quarters on DOT by Thatch is a apartment in Thimble Island, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $924.

From$107/night
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Waterfront vacation rentals in Thimble Island, MA

Discover vacation rentals close to the coast, water, and beach areas around Thimble Island, MA.

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

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

Apartment, Thimble Island

1 Bedroom Studio and 1 Full Bathroom-Close to Beach, Encore and TD Garden Arena. is a apartment in Thimble Island, 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 Thimble Island, 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 $1,091.

From$156/night
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Ocean Spray Inn - Thimble Island, MA

Ocean Spray Inn

Homestay, Thimble Island

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

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About Ocean Spray Inn

Ocean Spray Inn is a homestay in Thimble Island, 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 $1,448.

From$168/night
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Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches - Thimble Island, MA

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Apartment, Thimble Island

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches is a apartment in Thimble Island, with easy beach access, parking, and kitchen access. This stay gives…

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About Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches

Charming 1bedroom Apt with WiFi, AC in fabulous Winthrop Boston Airport Beaches is a apartment in Thimble Island, 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 $1,418.

From$203/night
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Unit 26 Chic Studio in Chelsea - Thimble Island, MA

Unit 26 Chic Studio in Chelsea

Apartment, Thimble Island

Unit 26 Chic Studio in Chelsea is a apartment in Thimble Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Unit 26 Chic Studio in Chelsea

Unit 26 Chic Studio in Chelsea is a apartment in Thimble Island, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,734.

From$248/night
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Vacation rentals with a pool in Thimble Island, MA

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

Cody's Place Winthrop Boston Logan Airport Beaches - Thimble Island, MA

Cody's Place Winthrop Boston Logan Airport Beaches

Apartment, Thimble Island

Cody's Place Winthrop Boston Logan Airport Beaches is a apartment in Thimble Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Cody's Place Winthrop Boston Logan Airport Beaches

Cody's Place Winthrop Boston Logan Airport Beaches is a apartment in Thimble Island, with pool access, 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 cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,066.

From$295/night
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Southie Condo - Near Subway - Bring Pets - Pool Table - Thimble Island, MA

Southie Condo - Near Subway - Bring Pets - Pool Table

Condo, Thimble Island

Southie Condo - Near Subway - Bring Pets - Pool Table is a condo in Thimble Island, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Southie Condo - Near Subway - Bring Pets - Pool Table

Southie Condo - Near Subway - Bring Pets - Pool Table is a condo in Thimble Island, 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,882.

From$697/night
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Beautiful Hingham Family Estate, Heated Pool and Game Room. - Thimble Island, MA

Beautiful Hingham Family Estate, Heated Pool and Game Room.

Holiday Home, Thimble Island

Beautiful Hingham Family Estate, Heated Pool and Game Room. is a holiday home in Thimble Island, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Beautiful Hingham Family Estate, Heated Pool and Game Room.

Beautiful Hingham Family Estate, Heated Pool and Game Room. is a holiday home in Thimble Island, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $13,524.

From$1,932/night
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Vacation rentals with parking in Thimble Island, MA

Find vacation rentals that make arriving by car easier.

HomeStay in Boston West Bellflower Street - Thimble Island, MA

HomeStay in Boston West Bellflower Street

B & B, Thimble Island

HomeStay in Boston West Bellflower Street is a b & b in Thimble Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About HomeStay in Boston West Bellflower Street

HomeStay in Boston West Bellflower Street is a b & b in Thimble Island, 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, onsite parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,290.

From$161/night
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Boston Historic Lower Mills - Thimble Island, MA

Boston Historic Lower Mills

Homestay, Thimble Island

Boston Historic Lower Mills is a homestay in Thimble Island, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Boston Historic Lower Mills

Boston Historic Lower Mills is a homestay in Thimble Island, 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 $1,420.

From$166/night
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3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt - Thimble Island, MA

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

Apartment, Thimble Island

3 Mi to Blue Hills Skiing & Hiking! Couple’s Apt is a apartment in Thimble Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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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 Thimble Island, 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 $1,480.

From$211/night
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Boston's Finest New Renovated Apartment - Thimble Island, MA

Boston's Finest New Renovated Apartment

Apartment, Thimble Island

Boston's Finest New Renovated Apartment is a apartment in Thimble Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Boston's Finest New Renovated Apartment

Boston's Finest New Renovated Apartment is a apartment in Thimble Island, 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,876.

From$268/night
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Pet-friendly vacation rentals in Thimble Island, MA

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

74R - 2BR Quincy - Romantic Stay near Wollaston Beach - Thimble Island, MA

74R - 2BR Quincy - Romantic Stay near Wollaston Beach

Apartment, Thimble Island

74R - 2BR Quincy - Romantic Stay near Wollaston Beach is a apartment in Thimble Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base…

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About 74R - 2BR Quincy - Romantic Stay near Wollaston Beach

74R - 2BR Quincy - Romantic Stay near Wollaston Beach is a apartment in Thimble Island, with pet-friendly space, easy beach access, 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 $2,016.

From$288/night
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Modern Brand New Dorchester Apartment! Quiet, Convenient & Minutes from Boston! - Thimble Island, MA

Modern Brand New Dorchester Apartment! Quiet, Convenient & Minutes from Boston!

Apartment, Thimble Island

Modern Brand New Dorchester Apartment! Quiet, Convenient & Minutes from Boston! is a apartment in Thimble Island, with pet-friendly space and a quieter setting. This stay gives travelers a…

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About Modern Brand New Dorchester Apartment! Quiet, Convenient & Minutes from Boston!

Modern Brand New Dorchester Apartment! Quiet, Convenient & Minutes from Boston! is a apartment in Thimble Island, 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 $2,276.

From$325/night
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Bohemian Paradise | Easy Access to All of Boston - Thimble Island, MA

Bohemian Paradise | Easy Access to All of Boston

Apartment, Thimble Island

Bohemian Paradise · Easy Access to All of Boston is a apartment in Thimble Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Bohemian Paradise | Easy Access to All of Boston

Bohemian Paradise · Easy Access to All of Boston is a apartment in Thimble Island, 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 $2,312.

From$330/night
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New 3 beds in Southie! W/D in unit. - Thimble Island, MA

New 3 beds in Southie! W/D in unit.

Holiday Home, Thimble Island

New 3 beds in Southie! W/D in unit. is a holiday home in Thimble Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About New 3 beds in Southie! W/D in unit.

New 3 beds in Southie! W/D in unit. is a holiday home in Thimble Island, 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

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

From$338/night
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Vacation rentals with a kitchen in Thimble Island, MA

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

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

Cozy basement/studio apartment with kitchenette and bathroom!

Apartment, Thimble Island

Cozy basement/studio apartment with kitchenette and bathroom! is a apartment in Thimble Island, 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 Thimble Island, 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 $1,198.

From$171/night
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3 Mi to Blue Hills Skiing & Hiking! Couples Apt - Thimble Island, MA

3 Mi to Blue Hills Skiing & Hiking! Couples Apt

Apartment, Thimble Island

3 Mi to Blue Hills Skiing & Hiking! Couples Apt is a apartment in Thimble Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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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 Thimble Island, 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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3 Mi to Franklin Park Zoo! Bright Residential Stay - Thimble Island, MA

3 Mi to Franklin Park Zoo! Bright Residential Stay

Condo, Thimble Island

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

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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 Thimble Island, 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 $1,676.

From$239/night
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NEWLY RENOVATED. 10 MINS TO BOTON. 3bds/2bths in a small friendly neighborhood. - Thimble Island, MA

NEWLY RENOVATED. 10 MINS TO BOTON. 3bds/2bths in a small friendly neighborhood.

Apartment, Thimble Island

NEWLY RENOVATED. 10 MINS TO BOTON. 3bds/2bths in a small friendly neighborhood. is a apartment in Thimble Island, with pet-friendly space and kitchen access. This stay gives travelers a…

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About NEWLY RENOVATED. 10 MINS TO BOTON. 3bds/2bths in a small friendly neighborhood.

NEWLY RENOVATED. 10 MINS TO BOTON. 3bds/2bths in a small friendly neighborhood. is a apartment in Thimble Island, 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 $2,543.

From$363/night
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