Holiday Homes in Middleton

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Middleton

"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
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
Stroll along the garden path to a serene seating area surrounded by lush greenery and trees.

Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

9.0 out of 10, Wonderful, (58)
"Nice quiet hideaway close to a great beach. Very private with rustic charm. "
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
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."
The price is AU$696
includes taxes & fees
4 Aug - 5 Aug
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
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 AU$1,296
includes taxes & fees
10 Aug - 11 Aug
Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean
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, (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
Centrally located charmer with expansive patio, board games, & central AC
Enjoy cooking in this well-equipped kitchen with a double oven, coffee maker, and kettle.

Centrally located charmer with expansive patio, board games, & central AC

7.6 out of 10, Good, (9)
"Beautiful property"
Centrally located charmer with expansive patio, board games, & central AC
Union Square House
Relax in a serene outdoor space with a seating area, hammock, and lush greenery.

Union Square House

9.6 out of 10, Exceptional, (77)
"Had a wonderful stay. Location great. House as described, clean, and comfortable. Would recommend for a stay. "
Union Square House
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, (237)
"We loved staying here! If we ever come back to Salem this is our first choice!"
Leslie's Retreat: Spacious home ideally located to everything
Spacious, New Renovation | Near T
Enjoy cooking in this well-equipped kitchen with a large island, sink, and ample counter space.

Spacious, New Renovation | Near T

10.0 out of 10, Exceptional, (7)
"The house was very nice, clean and comfortable. Had all the supplies we needed plus more included. Check-in and check-out were both super smooth. The host was very responsive. Overall great stay!"
Spacious, New Renovation | Near T
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and dishwasher.

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (83)
"This property is perfect for 2 travelers or for a small family. Close to everything, very clean and easy to get to. Would 100% stay here again!"
The price is AU$487
includes taxes & fees
9 Aug - 10 Aug
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
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, (1)
"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!
Whole House Steps from Pleasant Pond
Situated on a grassy area, this charming house features a front porch and a tranquil natural setting with a nearby body of water.

Whole House Steps from Pleasant Pond

9.6 out of 10, Exceptional, (43)
"Beautiful area next to the pond, quiet and peaceful!"
Whole House Steps from Pleasant Pond
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 AU$609
includes taxes & fees
4 Aug - 5 Aug
Entire Lower Level of the House, Across From The Beach
"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, (74)
"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
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
Cozy Apartment | Near T
Enjoy cooking in this well-lit kitchen with a copper stove top, stainless steel sink, and sleek cabinetry.

Cozy Apartment | Near T

8.6 out of 10, Excellent, (13)
"Great home. Close to almost everything "
Cozy Apartment | Near T
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
NEW 2BR Historic Marblehead Home+Minutes to Beach
Cozy living room with a sofa, lamp, and television, featuring a piano and bookshelf.

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (9)
"My family stayed in October for a quick weekend getaway. Great location and easy to get to from Boston. Would definitely book again. "
The price is AU$625
includes taxes & fees
7 Aug - 8 Aug
NEW 2BR Historic Marblehead Home+Minutes to Beach
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.
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Relax on the deck with a comfortable wicker chair and enjoy the serene surroundings.

Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!

10.0 out of 10, Exceptional, (18)
"Definitely will be staying there again!"
The price is AU$495
includes taxes & fees
3 Sept - 4 Sept
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
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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