Holiday Homes in Middleton

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Featured Holiday Homes in Middleton

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

9.8 out of 10, Exceptional, (167)
"So much better than staying at a hotel and separating our group of seven. Awesome stay, 10 out of 10 recommend"
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (237)
"We rented this house to stay for my son’s wedding in Salem. The house was fantastic and quaint. Megan is a great host and very responsive. Would definitely rent again if we’re in Salem!"
Leslie's Retreat: Spacious home ideally located to everything

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

10.0 out of 10, Exceptional, (14)
"We had a great time at Captains lookout. The pictures were accurate and we love the view from the roof. The host was very accommodating and helpful. "
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (126)
"We stayed here for four days. It’s very clean nice beautiful place."
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Quaint getaway with full kitchen and lush yard - close to the beach and downtown

9.0 out of 10, Wonderful, (118)
"We liked the location. It was close enough to walk to town. House had everything we needed and the 2 coffee pots was a plus for us."
Quaint getaway with full kitchen and lush yard - close to the beach and downtown

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

9.4 out of 10, Exceptional, (8)
The price is AU$1,389
includes taxes & fees
20 Aug - 21 Aug
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

9.8 out of 10, Exceptional, (75)
"Had the best family vacation at the Rocky Neck Hideaway, from the location, to the host, to the amenities, everything was excellent. The whole stay exceeded our expections and we will be back! "
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

9.6 out of 10, Exceptional, (42)
"Property was clean, well decorated in Gloucester vacation decor, inviting! Check-in was easy, and we had a great time together. Would definitely like to visit here again!"
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

Cloud 9 Lounge - Aviation-Themed Designer Flat

Cloud 9 Lounge - Aviation-Themed Designer Flat

Charming 3-bedroom house in the HEART of SALEM!

10.0 out of 10, Exceptional, (2)
"The house was clean and beautiful and easily fit 6 people. The house was in walking distance from all attractions and restaurants on Essex Street. I would recommend this house and would stay there again."
Charming 3-bedroom house in the HEART of SALEM!

House near down town Salem

9.6 out of 10, Exceptional, (49)
"The property was very well maintained and the owner was very helpful. Easy parking and very walkable distance to downtown area. The only thing we didn't like was the placement of the tp holder but their isnt much they can do with the limited space. Overall very happy with the visit and would recommend to anyone."
The price is AU$601
includes taxes & fees
10 Aug - 11 Aug
House near down town Salem

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (16)
"Loved getting to visit the beach and the short drive to Salem!"
The price is AU$617
includes taxes & fees
7 Sept - 8 Sept
Entire Lower Level of the House, Across From The Beach

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

10.0 out of 10, Exceptional, (65)
"Really enjoyed the house. Great location, easy checking in. They even had a decorated Christmas tree for us."
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Clean, Contemporary Escape Near T

8.4 out of 10, Very good, (6)
"One parent and three teenagers in town for college tours. The location was “20” minutes via uber which was great. Everyone had room to decompress at the end of the day. Showers were great and beds were super comfortable. We will strongly consider staying there again for our next visit. "
Clean, Contemporary Escape Near T

The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.

9.8 out of 10, Exceptional, (36)
"Was a great spot for my spouse and I to visit again. We look forward to visiting this spot next year! "
The Bungalow @ Elm is located in the heart of Old Town Marblehead, MA.

Spacious 3-bedroom house with WiFi, AC in Cambridge- walk to Harvard/MIT+parking

Spacious 3-bedroom house with WiFi, AC in Cambridge- walk to Harvard/MIT+parking

Lake Access 4 Bed 3 Full Bath

10.0 out of 10, Exceptional, (17)
"What a great place to cook dinner and have a night with the girls! "
The price is AU$1,570
includes taxes & fees
10 Aug - 11 Aug
Lake Access 4 Bed 3 Full Bath

Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport

10.0 out of 10, Exceptional, (5)
"Nice neighborhood. Placed clean and cozy. Big kitchen area for hanging out. "
Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport

Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

8.8 out of 10, Excellent, (29)
"Excellent property; easy to work with owners."
The price is AU$923
includes taxes & fees
11 Aug - 12 Aug
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

2.0 star property
9.8 out of 10, Exceptional, (6)
"Lived the location and light!!Thanks!!"
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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