Vacation rentals in Middlesex County, MA

40 available vacation rental offers

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Best vacation rentals and Airbnb offers in Middlesex County, MA

Train to Boston! Cozy Apartment in Winchester - Middlesex County, MA

Train to Boston! Cozy Apartment in Winchester

Apartment, Middlesex County

Train to Boston! Cozy Apartment in Winchester is a apartment in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Middlesex County, 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 $1,012.

From$119/night
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Cozy self-contained apartment with Private Entrance. - Middlesex County, MA

Cozy self-contained apartment with Private Entrance.

Apartment, Middlesex County

Cozy self-contained apartment with Private Entrance. is a apartment in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cozy self-contained apartment with Private Entrance.

Cozy self-contained apartment with Private Entrance. is a apartment in Middlesex County, 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 $861.

From$123/night
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Train to Boston! Cozy Apartment in Winchester - Middlesex County, MA

Train to Boston! Cozy Apartment in Winchester

Apartment, Middlesex County

Train to Boston! Cozy Apartment in Winchester is a apartment in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Middlesex County, 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 $897.

From$128/night
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The Inn on the Horse Farm - Middlesex County, MA

The Inn on the Horse Farm

Guest House, Middlesex County

The Inn on the Horse Farm is a guest house in Middlesex County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Inn on the Horse Farm

The Inn on the Horse Farm is a guest house in Middlesex County, 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 parking in Middlesex County, MA

Find vacation rentals that make arriving by car easier.

Deluxe and Bright 3Br, King Bed,W/D,Parking - Middlesex County, MA

Deluxe and Bright 3Br, King Bed,W/D,Parking

Condo, Middlesex County

Deluxe and Bright 3Br, King Bed,W/D,Parking is a condo in Middlesex County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Deluxe and Bright 3Br, King Bed,W/D,Parking

Deluxe and Bright 3Br, King Bed,W/D,Parking is a condo in Middlesex County, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,954.

From$279/night
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Experience Classic Charm in a Cozy 115-Year-Old Colonial - Middlesex County, MA

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

Apartment, Middlesex County

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

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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 Middlesex County, 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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Private 3-bedroom in Billerica, cool AC - Shared Backyard - Basement Occupied - Middlesex County, MA

Private 3-bedroom in Billerica, cool AC - Shared Backyard - Basement Occupied

Holiday Home, Middlesex County

Private 3-bedroom in Billerica, cool AC - Shared Backyard - Basement Occupied is a holiday home in Middlesex County, with parking, kitchen access, and room for a group. This stay gives…

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About Private 3-bedroom in Billerica, cool AC - Shared Backyard - Basement Occupied

Private 3-bedroom in Billerica, cool AC - Shared Backyard - Basement Occupied is a holiday home in Middlesex County, 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 $2,419.

From$346/night
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Lakeview Getaway With Hot Tub - Middlesex County, MA

Lakeview Getaway With Hot Tub

Holiday Home, Middlesex County

Lakeview Getaway With Hot Tub is a holiday home in Middlesex County, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lakeview Getaway With Hot Tub

Lakeview Getaway With Hot Tub is a holiday home in Middlesex County, with 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, free wifi, beachfront, beach front, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,940.

From$395/night
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Pet-friendly vacation rentals in Middlesex County, MA

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

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly - Middlesex County, MA

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly

Holiday Home, Middlesex County

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly is a holiday home in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly

Contemporary house on 8 acres of wild flowers, trees and trails; pet friendly is a holiday home in Middlesex County, 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 $2,255.

From$322/night
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Beautiful new apartment 2bed/2bath Waltham - Middlesex County, MA

Beautiful new apartment 2bed/2bath Waltham

Apartment, Middlesex County

Beautiful new apartment 2bed/2bath Waltham is a apartment in Middlesex County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Beautiful new apartment 2bed/2bath Waltham

Beautiful new apartment 2bed/2bath Waltham is a apartment in Middlesex County, 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, pet friendly, pets friendly, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,461.

From$352/night
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Modern Comfort. Enjoy this centrally located and stylish apartment! - Middlesex County, MA

Modern Comfort. Enjoy this centrally located and stylish apartment!

Apartment, Middlesex County

Modern Comfort. Enjoy this centrally located and stylish apartment! is a apartment in Middlesex County. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Modern Comfort. Enjoy this centrally located and stylish apartment!

Modern Comfort. Enjoy this centrally located and stylish apartment! is a apartment in Middlesex County. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,551.

From$364/night
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Spacious vacation townhome unit with a pool - Middlesex County, MA

Spacious vacation townhome unit with a pool

Holiday Home, Middlesex County

Spacious vacation townhome unit with a pool is a holiday home in Middlesex County, 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 Middlesex County, 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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Vacation rentals with a kitchen in Middlesex County, MA

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

Charming Townhouse 12 minutes to Boston - Middlesex County, MA

Charming Townhouse 12 minutes to Boston

Apartment, Middlesex County

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

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About Charming Townhouse 12 minutes to Boston

Charming Townhouse 12 minutes to Boston is a apartment in Middlesex County, 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 - Middlesex County, MA

Remodeled Townhouse close to Boston

Holiday Home, Middlesex County

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

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About Remodeled Townhouse close to Boston

Remodeled Townhouse close to Boston is a holiday home in Middlesex County, 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 and modern 3 Bedroom 2 full BR. - Middlesex County, MA

Beautiful and modern 3 Bedroom 2 full BR.

Holiday Home, Middlesex County

Beautiful and modern 3 Bedroom 2 full BR. is a holiday home in Middlesex County, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Beautiful and modern 3 Bedroom 2 full BR.

Beautiful and modern 3 Bedroom 2 full BR. is a holiday home in Middlesex County, 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, free wifi, kitchen, with kitchen, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,969.

From$424/night
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18th Century Farm House in Center of Carlisle - Middlesex County, MA

18th Century Farm House in Center of Carlisle

Holiday Home, Middlesex County

18th Century Farm House in Center of Carlisle is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 18th Century Farm House in Center of Carlisle

18th Century Farm House in Center of Carlisle is a holiday home in Middlesex County, 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 $3,268.

From$467/night
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Family-friendly vacation rentals in Middlesex County, MA

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

3-Bedroom Apartment in Ayer, Steps from Train, Easy Boston Access, Free Parking. - Middlesex County, MA

3-Bedroom Apartment in Ayer, Steps from Train, Easy Boston Access, Free Parking.

Apartment, Middlesex County

3-Bedroom Apartment in Ayer, Steps from Train, Easy Boston Access, Free Parking. is a apartment in Middlesex County, with parking, kitchen access, and room for a group. This stay gives…

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About 3-Bedroom Apartment in Ayer, Steps from Train, Easy Boston Access, Free Parking.

3-Bedroom Apartment in Ayer, Steps from Train, Easy Boston Access, Free Parking. is a apartment in Middlesex County, 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 $1,774.

From$253/night
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1000ft² 2BR with Free Parking, King Bed, WFH Setup, Near Harvard, MIT, & Tufts - Middlesex County, MA

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

Holiday Home, Middlesex County

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

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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 Middlesex County, 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 $2,060.

From$294/night
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Cozy Lake Cottage in charming Dunstable - Middlesex County, MA

Cozy Lake Cottage in charming Dunstable

Cottage, Middlesex County

Cozy Lake Cottage in charming Dunstable is a cottage in Middlesex County. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Cozy Lake Cottage in charming Dunstable

Cozy Lake Cottage in charming Dunstable is a cottage in Middlesex County. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,079.

From$297/night
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Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods - Middlesex County, MA

Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods

Cottage, Middlesex County

Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods is a cottage in Middlesex County, with pool access, kitchen access, and a quieter setting. This stay gives…

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About Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods

Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods is a cottage in Middlesex County, with pool access, 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: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,129.

From$304/night
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