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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Middleton Vacation Homes

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Staircase leads to a landing with a control panel.

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

9.8 out of 10, Exceptional, (168)
"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
Enter a serene hallway with a door featuring a frosted glass panel, adorned with a wreath and a potted plant on a nearby table.

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (238)
"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
Fridge, microwave, oven, stovetop

"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
Enjoy cooking in this well-equipped kitchen with sleek cabinetry, granite countertop, and stainless steel appliances.

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
Compact kitchen with microwave, oven, and coffee maker, featuring a geometric-patterned backsplash and ceiling light fixture.

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
Stunning grand staircase with a chandelier and arched doorway.

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

9.4 out of 10, Exceptional, (8)
The price is CA $894
CA $1,230 total
includes taxes & fees
Aug 20 - Aug 21
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Enjoy a peaceful retreat on this deck surrounded by lush trees and a charming fence.

"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!
Relax in a serene outdoor seating area surrounded by lush greenery and a tranquil atmosphere.

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
TV, books

Cloud 9 Lounge - Aviation-Themed Designer Flat

Cloud 9 Lounge - Aviation-Themed Designer Flat
Charming 3-bedroom house in the HEART of SALEM!
Paper towels

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
Stunning two-story building with a central entrance and symmetrical facade.

House near down town Salem

9.6 out of 10, Exceptional, (50)
"Had a weekend getaway with my mom and sister for Mothers Day and this was the perfect spot to stay! It was a quick walk across the bridge to get to downtown Salem and all of the shops and museums. Owners were super helpful and responsive, and the house was clean and beautiful. It was nice and quiet and we felt so safe the whole time. Would definitely rebook if we return to the area!! "
The price is CA $334
CA $598 total
includes taxes & fees
Aug 18 - Aug 19
House near down town Salem
Entire Lower Level of the House, Across From The Beach
Walk along the pier and enjoy the serene views of the calm water.

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 CA $316
CA $546 total
includes taxes & fees
Sep 7 - Sep 8
Entire Lower Level of the House, Across From The Beach
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Enjoy casual dining and cooking in this well-appointed kitchen with a central island, stove, and modern appliances.

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
Relax in this stylish living room with a large flat-screen TV, comfortable sofa, and cozy bench.

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.
Enjoy a peaceful retreat with a garden view from the comfort of this serene room, featuring a table for two and a cozy corner with a plant.

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
Fridge, microwave, oven, stovetop

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
Enjoy cooking in this well-equipped kitchen with a central island, bar stools, and stainless steel appliances.

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 CA $592
CA $1,291 total
includes taxes & fees
Aug 11 - Aug 12
Lake Access 4 Bed 3 Full Bath
Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport
Relax in a cozy seating area with a fireplace, flat-screen TV, and large windows offering views of the outdoors.

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

10.0 out of 10, Exceptional, (6)
"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
Stylish two-story home with a central entrance, flanked by windows with shutters, and a charming picket fence.

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 CA $370
CA $737 total
includes taxes & fees
Aug 11 - Aug 12
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.
Cozy living space with a sofa, coffee table, and reading materials.

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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Top Middleton Hotel Reviews

Encore Boston Harbor

Encore Boston Harbor

10/10 Excellent
"Check in was amazing. Peter, the bellman, was the most professional, happy, informative bellman I have had anywhere in the world. "
Jay 1-night trip
Posted 14 hours ago
Encore Boston Harbor