Vacation rentals in Middleton, MA

68 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Middleton, MA

Train to Boston! Cozy Apartment in Winchester - Middleton, MA

Train to Boston! Cozy Apartment in Winchester

Apartment, Middleton

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

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About Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Middleton, 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 $955.

From$80/night
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Queen Bed - Boston - RM 2 - Middleton, MA

Queen Bed - Boston - RM 2

Homestay, Middleton

Queen Bed - Boston - RM 2 is a homestay in Middleton, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Queen Bed - Boston - RM 2

Queen Bed - Boston - RM 2 is a homestay in Middleton, 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 $1,165.

From$109/night
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Queen Bed - Boston - RM 3 - Middleton, MA

Queen Bed - Boston - RM 3

Homestay, Middleton

Queen Bed - Boston - RM 3 is a homestay in Middleton, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Queen Bed - Boston - RM 3

Queen Bed - Boston - RM 3 is a homestay in Middleton, 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 $1,166.

From$109/night
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Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93 - Middleton, MA

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

Apartment, Middleton

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93 is a apartment in Middleton, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93

Sleep up to 4 Guest New Apt. 10 mins to Boston Easy to I-93 is a apartment in Middleton, 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 $1,120.

From$114/night
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Best Middleton, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Train to Boston! Cozy Apartment in Winchester - Middleton, MA

Train to Boston! Cozy Apartment in Winchester

Apartment, Middleton

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

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About Train to Boston! Cozy Apartment in Winchester

Train to Boston! Cozy Apartment in Winchester is a apartment in Middleton, 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 $1,020.

From$120/night
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6 Mi to Boston Common: Apt in Medford! - Middleton, MA

6 Mi to Boston Common: Apt in Medford!

Apartment, Middleton

6 Mi to Boston Common: Apt in Medford! is a apartment in Middleton, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 6 Mi to Boston Common: Apt in Medford!

6 Mi to Boston Common: Apt in Medford! is a apartment in Middleton, 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 $2,126.

From$192/night
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Modern Three Bedroom Condo - Near Boston - Middleton, MA

Modern Three Bedroom Condo - Near Boston

Condo, Middleton

Modern Three Bedroom Condo - Near Boston is a condo in Middleton, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston is a condo in Middleton, 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 $2,731.

From$291/night
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Smoke FREE Studio- walk to beaches, downtown! 5 min drive to Historic Salem! - Middleton, MA

Smoke FREE Studio- walk to beaches, downtown! 5 min drive to Historic Salem!

Apartment, Middleton

Smoke FREE Studio- walk to beaches, downtown! 5 min drive to Historic Salem! is a apartment in Middleton, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Smoke FREE Studio- walk to beaches, downtown! 5 min drive to Historic Salem!

Smoke FREE Studio- walk to beaches, downtown! 5 min drive to Historic Salem! is a apartment in Middleton, 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 $3,524.

From$332/night
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Best Pet-Friendly Vacation Rentals in Middleton, MA

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

Located north of Boston/ comfort and relaxation in your home away from home - Middleton, MA

Located north of Boston/ comfort and relaxation in your home away from home

Holiday Home, Middleton

Located north of Boston/ comfort and relaxation in your home away from home is a holiday home in Middleton, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Located north of Boston/ comfort and relaxation in your home away from home

Located north of Boston/ comfort and relaxation in your home away from home is a holiday home in Middleton, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,455.

From$157/night
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Luxury apartment with gym, steps from commuter rail #4011 - Middleton, MA

Luxury apartment with gym, steps from commuter rail #4011

Apartment, Middleton

Luxury apartment with gym, steps from commuter rail #4011 is a apartment in Middleton, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Luxury apartment with gym, steps from commuter rail #4011

Luxury apartment with gym, steps from commuter rail #4011 is a apartment in Middleton, 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 $2,269.

From$257/night
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Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly - Middleton, MA

Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly

Apartment, Middleton

Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly is a apartment in Middleton, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly

Historic 1803 Salem 1BR l Walk to Haunted Happenings l SMALL DOG friendly is a apartment in Middleton, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,473.

From$258/night
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Spacious 7-Room House Near Boston & Salem With Yard and Parking - Middleton, MA

Spacious 7-Room House Near Boston & Salem With Yard and Parking

Holiday Home, Middleton

Spacious 7-Room House Near Boston & Salem With Yard and Parking is a holiday home in Middleton, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Spacious 7-Room House Near Boston & Salem With Yard and Parking

Spacious 7-Room House Near Boston & Salem With Yard and Parking is a holiday home in Middleton, 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 $3,078.

From$327/night
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Best Middleton, MA vacation rentals with a kitchen

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

Coastal Charm – Walk to Beach or Train! - Middleton, MA

Coastal Charm – Walk to Beach or Train!

Condo, Middleton

Coastal Charm – Walk to Beach or Train! is a condo in Middleton, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Coastal Charm – Walk to Beach or Train!

Coastal Charm – Walk to Beach or Train! is a condo in Middleton, with 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,274.

From$225/night
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Salem Haunted Happenings Retreat - Middleton, MA

Salem Haunted Happenings Retreat

Apartment, Middleton

Salem Haunted Happenings Retreat is a apartment in Middleton, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Salem Haunted Happenings Retreat

Salem Haunted Happenings Retreat is a apartment in Middleton, 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: kitchen, with kitchen, tv, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,348.

From$275/night
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Hocus Pocus Season is here! Don’t miss it! - Middleton, MA

Hocus Pocus Season is here! Don’t miss it!

Apartment, Middleton

Hocus Pocus Season is here! Don’t miss it! is a apartment in Middleton, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Hocus Pocus Season is here! Don’t miss it!

Hocus Pocus Season is here! Don’t miss it! is a apartment in Middleton, 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 $2,707.

From$285/night
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Downtown Salem Retreat 2BD 3rd Floor - Middleton, MA

Downtown Salem Retreat 2BD 3rd Floor

Apartment, Middleton

Downtown Salem Retreat 2BD 3rd Floor is a apartment in Middleton, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Downtown Salem Retreat 2BD 3rd Floor

Downtown Salem Retreat 2BD 3rd Floor is a apartment in Middleton, 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: kitchen, with kitchen, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,660.

From$315/night
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Our Favorite Family-Friendly Vacation Rentals in Middleton, MA

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

House on A+ school area w/AC & W/D - Middleton, MA

House on A+ school area w/AC & W/D

Holiday Home, Middleton

House on A+ school area w/AC & W/D is a holiday home in Middleton, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About House on A+ school area w/AC & W/D

House on A+ school area w/AC & W/D is a holiday home in Middleton, 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,777.

From$192/night
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5 Mi to TD Garden: Quiet Medford Getaway! - Middleton, MA

5 Mi to TD Garden: Quiet Medford Getaway!

Cottage, Middleton

5 Mi to TD Garden: Quiet Medford Getaway! is a cottage in Middleton, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About 5 Mi to TD Garden: Quiet Medford Getaway!

5 Mi to TD Garden: Quiet Medford Getaway! is a cottage in Middleton, with parking, 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 parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,574.

From$303/night
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The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston - Middleton, MA

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston

Holiday Home, Middleton

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston is a holiday home in Middleton, with kitchen access and room for a group. This stay gives travelers a comfortable…

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About The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston is a holiday home in Middleton, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,158.

From$341/night
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Family-Friendly Salem Apt: Near Dtwn Sites! - Middleton, MA

Family-Friendly Salem Apt: Near Dtwn Sites!

Condo, Middleton

Family-Friendly Salem Apt: Near Dtwn Sites! is a condo in Middleton, 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 Family-Friendly Salem Apt: Near Dtwn Sites!

Family-Friendly Salem Apt: Near Dtwn Sites! is a condo in Middleton, 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 $3,832.

From$387/night
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