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Compare 555 Vacation Homes in Middleton with updated reviews, rates, and availability.

WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
9.6 out of 10, Exceptional, (59)
"Great little property right in the middle of it all. Walking distance to everything. Super cute, and comfortable. We really were only in it to sleep really, with so much do to in town."
The price is AED 1,377
AED 2,462 total
includes taxes & fees
29 Sep - 30 Sep
WALK TO WATER & HISTORIC DISTRICT! PRIVATE !!Large first floor apartment
CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA
2.0 star property
9.0 out of 10, Wonderful, (6)
"We stayed for a short trip for a concert, and it worked out great! The space was very comfortable and clean, and was very conveniently located! Would stay again!"
CityScape: Sleek Urban Oasis; Central AC, Parking, Near: Boston, Casino, Airport, Parks, MBTA
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
9.6 out of 10, Exceptional, (98)
"Clean and comfy. Perfect location. Great view and close to the sights."
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Modern home-like 3BR2BA Retreat/Minutes to T
9.6 out of 10, Exceptional, (8)
"Beautiful and spotless (and I mean spotless) 2nd floor apartment. Easy check in/out. Easy street parking on weekends (Friday after 7pm through Monday 7am) for non-residents. Property owner lives 2 blocks away and is easy to reach by phone or messaging through the Vrbo app. One of the smoke detectors kept inadvertently going off as soon as we arrived. I messaged the owner, who replied back and showed up in less than five minutes. One note (that has nothing to do with the space), when we...
The price is AED 1,392
AED 2,795 total
includes taxes & fees
30 Sep - 1 Oct
Modern home-like 3BR2BA Retreat/Minutes to T
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
9.4 out of 10, Exceptional, (29)
"Just what we needed for the night. Air conditioners and tv in each room, comfortable pull out couches. Clean and dog friendly. "
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
Leslie's Retreat: Spacious home ideally located to everything
10.0 out of 10, Exceptional, (212)
"We were all very happy with our stay at this house...very clean, comfortable and peaceful place. We're already looking forward to our next vacation here."
Leslie's Retreat: Spacious home ideally located to everything
Copley House - 1 Bedroom Suite
8.8 out of 10, Excellent, (3)
"Great property, small efficiency style apartment. Great location, great neighborhood. Parking in the 35 Westland Garage."
The price is AED 1,212
AED 1,566 total
includes taxes & fees
30 Sep - 1 Oct
Copley House - 1 Bedroom Suite
Stunning Beach Cottage just steps from Marblehead Harbor and Town
10.0 out of 10, Exceptional, (37)
"A sweet, small summer cottage within walking distance of much of Marblehead. The owner has decorated it well, and has provided everything one might need. Excellent communications, except VRBO listing lists various number of bedrooms. There are two bedrooms, one bath."
Stunning Beach Cottage just steps from Marblehead Harbor and Town
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
10.0 out of 10, Exceptional, (4)
"My wife and I stayed for several days and the apartment was perfect for our needs. Everything in the apartment was spotless, fresh linens and soft towels. The multiple decks offer a variety of places to sit, read and listen to the ocean. The neighborhood was super safe and quiet; you could hear a pin drop at night and the breeze off the ocean was delightful. We enjoyed the local beaches, had dinner with friends at Tonnos and breakfast at the Source bakery. Rockport is a short drive and there...
The price is AED 661
AED 1,362 total
includes taxes & fees
16 Oct - 17 Oct
"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester
Charming family home conveniently placed near water, beaches, & more
3.0 star property
9.8 out of 10, Exceptional, (9)
"Absolutely outstanding!! The entire house is full of everything you will need! Great job by the owner to go way, way beyond what is actually required. I'll be going back there again and again."
Charming family home conveniently placed near water, beaches, & more
Revere Luxury House ,private beach
2.0 star property
10.0 out of 10, Exceptional, (1)
"We travel in a 45' Coach. Could not find a RV Park for the week-end. This unit was available and a perfect fit for our time in Boston. "
The price is AED 1,286
AED 2,343 total
includes taxes & fees
29 Sep - 30 Sep
Revere Luxury House ,private beach
Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces
8.4 out of 10, Very Good, (50)
"Instant communication with property management during stay; everything as indicated in website. Everyone was very happy!"
Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
10.0 out of 10, Exceptional, (50)
"Beautiful property in a nice location. 10 min to Fenway, 40 min walk to downtown. Suggested property improvements, bedroom lighting, shower water pressure and hot water"
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Union Square House
9.6 out of 10, Exceptional, (57)
"My family and I were in for a wedding and this turned out to be literally around the corner from the venue. The location was convenient, but also in a lovely part of town. The house itself is a mix of dated construction and modern upgrades. The bathroom, in particular, is quite comfortable. On the flip side, the stairs going up to the top floor bedrooms are very, very steep. "
Union Square House
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
9.6 out of 10, Exceptional, (70)
"Friends weekend, we had a blast and loved the house. "
The price is AED 1,469
AED 2,720 total
includes taxes & fees
1 Oct - 2 Oct
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Wonderful Renovated Family Friendly Home Close to Boston and Lexington
10.0 out of 10, Exceptional, (54)
"Had a great time here. Nice neighbor and plenty of groceries store, restaurants close by. The owner gets right back promptly with any questions or concerns. Overall exceptional house would highly recommend. ☺️"
Wonderful Renovated Family Friendly Home Close to Boston and Lexington
Modern Smart Home with EV charger Near Boston & Harvard, 0.7 miles to MBTA
9.8 out of 10, Exceptional, (10)
"We had a very pleasant stay. The house is very clean and very well kept. The location is convenient to neighborhood food or drink shopping. We can feel the host makes real efforts to make the place comfortable for its guests. The open floor plan makes the place very welcoming for family or friend get together. The host is also very responsive to questions relating to our stay before and after our arrival. We would recommend this place ."
Modern Smart Home with EV charger Near Boston & Harvard, 0.7 miles to MBTA
The View: A classic New England cottage with panoramic ocean views.
10.0 out of 10, Exceptional, (22)
"Million dollar view, comfortable and well appointed. Everything we needed."
The View: A classic New England cottage with panoramic ocean views.
3Bdr Salem Home Getaway
7.8 out of 10, Good, (7)
"Excellent communitcation with the host. The place was great and exactly what we needed for our trip to Salem. Great place for resting your head but may not be ideal for large gatherings. If you have issues with stairs this is not the place for you but the place was clean, located jn a safe area, quick walking distance for Salem festivities and doughnut shops. Would stay again!"
3Bdr Salem Home Getaway
Coastal Modern Beachfront Chalet, sleeps 10+
Coastal Modern Beachfront Chalet, sleeps 10+
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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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Other property types in Middleton

Global Luxury Suites Downtown Boston
4.0 star property
8.0 out of 10, Very Good, (481)
"Excellent stay! Right in Chinatown. So much better than a standard hotel. We stayed in a 1bed and had a washer/dryer which was SO convenient. Walkable to many sites, food etc. Would stay here again for sure . "
The price is AED 750
AED 1,320 total
includes taxes & fees
29 Sep - 30 Sep
Global Luxury Suites Downtown Boston
Maverick Suites at 28 Fenway
2.5 star property
9.2 out of 10, Wonderful, (123)
"It was in a good location for walking Boston. "
The price is AED 437
AED 861 total
includes taxes & fees
29 Sep - 30 Sep
Maverick Suites at 28 Fenway
Temple Place Suites
2.5 star property
6.8 out of 10, (146)
"Location is everything! Clean and comfortable and exactly as advertised "
The price is AED 456
AED 726 total
includes taxes & fees
28 Oct - 29 Oct
Temple Place Suites
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.