Search Vacation Homes in Middleton

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 719 Vacation Homes in Middleton with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (158)
"Great location for those who like to walk."
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Clean, Contemporary Escape | Near T
TV, offices

Clean, Contemporary Escape | Near T

10.0 out of 10, Exceptional, (1)
"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
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Fridge, microwave, oven, stovetop

2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

9.0 out of 10, Wonderful, (26)
"I enjoyed my trip to Boston in this VRBO. It's very easy to get ubers in and out of the city which is awesome. As a house cleaner, I just have a couple of observations that I think the host should take into consideration. The hand towel was messed up on the hanger (making it look used by other guests). There was lint (??) in the drain of the kitchen sink. And the fan in the living room 100% needs some attention. I am not a picky person but some people are so I wanted to point those out....
The price is AED 749
AED 1,666 total
includes taxes & fees
13 Apr - 14 Apr
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (72)
"Clean and convenient. Loud neighbors"
The price is AED 364
AED 1,026 total
includes taxes & fees
16 Apr - 17 Apr
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
4 bedrooms, in-room safe, desk, iron/ironing board

Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

10.0 out of 10, Exceptional, (67)
"My family and I had a wonderful stay at Luxury Bayside Jewel in Squantum, MA, over the holidays, and I cannot recommend this property enough. From the start, the property manager, Susan, made the experience seamless. She was incredibly responsive to all my questions before and during the trip, addressing even the smallest details—like when and where to put the trash out—with patience and care.The home itself exceeded all expectations. Thoughtful touches made us feel welcome from the moment we...
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Peek-a-Boo Lake Views & Yard: Windham Home
Terrace/patio

Peek-a-Boo Lake Views & Yard: Windham Home

8.8 out of 10, Excellent, (3)
"Lovely home in sweet neighborhood. The host was responsive to my communications. Very positive experience. "
Peek-a-Boo Lake Views & Yard: Windham Home
Entire Home 2BR 2BTH Quite Area with parking
Smart TV, fireplace, computer monitors

Entire Home 2BR 2BTH Quite Area with parking

10.0 out of 10, Exceptional, (1)
"The Quiet Single Family House was the perfect place to stay for our group of a mom and 3 college-aged girls. We had plenty of space, the home was very clean and comfortable, and we were central to everything we wanted to do in the area. The neighborhood was peaceful and it wasn’t far to restaurants and grocery stores. The homeowner was a great source of information on things to do in the area as well as very responsive to any questions I had. I’d definitely rent from her again. We had a...
Entire Home 2BR 2BTH Quite Area with parking
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (57)
"My mission team stayed there for the weekend. Perfect accommodation for the jobs and location that we worked at. Thank You"
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck
Fridge, microwave, oven, stovetop

Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck

9.6 out of 10, Exceptional, (41)
"House was perfect for our needs. Clean and great location. The only suggestion is to equip house better for cooking meals. "
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck
Incredible Boston Home | Near T
TV, offices

Incredible Boston Home | Near T

Incredible Boston Home | Near T
Belmont Home < 3 Mi to Harvard Square!
Microwave, stovetop, dishwasher, coffee/tea maker

Belmont Home < 3 Mi to Harvard Square!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We were in town for a family gathering nearby, and Joanne’s home was the perfect resting spot for the four of us. The beds were very comfortable, the shower was great, and the kitchen was well stocked with cooking supplies. Joanne was an incredibly thoughtful, kind, and responsive host. We will definitely stay here next time we are in town. Thank you, Joanne!"
The price is AED 500
AED 986 total
includes taxes & fees
14 Apr - 15 Apr
Belmont Home < 3 Mi to Harvard Square!
Beautiful renovated 3 bedroom apt near Boston.
Fridge, microwave, oven, stovetop

Beautiful renovated 3 bedroom apt near Boston.

9.8 out of 10, Exceptional, (74)
"Very clean and quiet home. Convenient to downtown and great neighborhood. Loved the park across the street for our dog. Beautiful interior. Will definitely stay there again."
Beautiful renovated 3 bedroom apt near Boston.
Enchanting Hidden Door Escape
Fridge, microwave, oven, stovetop

Enchanting Hidden Door Escape

2.0 star property
10.0 out of 10, Exceptional, (11)
"This was a convenient pick for us, being only about 1.5 miles from other family members home. We didn't spend much time there but it was very comfortable. The weather got very cold for a few days, below freezing and we had no hot water upstairs. I contacted management and they had someone out within hours, ON A SUNDAY and started addressing the problem. I would stay here again."
The price is AED 956
AED 2,296 total
includes taxes & fees
13 Apr - 14 Apr
Enchanting Hidden Door Escape
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Fridge, microwave, oven, stovetop

CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses

2.0 star property
9.6 out of 10, Exceptional, (16)
"Clean, bright, new, comfortable, excellent space. Really appreciated the welcome package. The kitchen is very well stocked with spices and other perks. The book of instructions on the counter is clear and helpful. Nice area, easy walk to pizza and Dunkin. Appreciated the owner accommodating our Sunday time request Would highly recommend this place."
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
Smart TV, fireplace

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

10.0 out of 10, Exceptional, (60)
"Perfect little house! "
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
Leslie's Retreat: Spacious home ideally located to everything
Fridge, microwave, oven, stovetop

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (226)
"Checkin was very easy, home was wonderful and very clean.Communication with hosts was quick.Allowed us to checkin with a very small fee, very much appreciated!Thank You!"
Leslie's Retreat: Spacious home ideally located to everything
Massachusetts Abode w/ Deck & Grill: Near Beaches!
Fridge, microwave, stovetop, dishwasher

Massachusetts Abode w/ Deck & Grill: Near Beaches!

10.0 out of 10, Exceptional, (9)
"My husband, sister, and brother in law and I stayed here for 3 nights and were very pleased. The house was cozy and in a peaceful neighborhood. We loved staying here however the water does take a while to heat up and the shower water pressure was very low. Minor details but overall recommended. "
Massachusetts Abode w/ Deck & Grill: Near Beaches!
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Exterior

Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

9.2 out of 10, Wonderful, (25)
"I reserved the house for 4 days just so my 17 year old daughter and her 3 best friends could spend quality time in Boston on her birthday. We really liked the house; it’s a nice space with all the necessities and very cozy. it was a great fit for our family and we truly enjoyed it. It’s actually minutes to everything in Boston, and we would stay there again if we come back into town. "
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
TV, fireplace, books

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

9.8 out of 10, Exceptional, (31)
"We visited Gloucester with our 3 adult children and the 5 of us had plenty of space in this great home. Walking distance to great lobster, coffee shops and bakeries. "
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Private kitchen

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2.0 star property
9.6 out of 10, Exceptional, (4)
"My group with 4 adults and 2 teens was very comfortable in this home. It is in an upscale neighborhood, There is a park directly behind the property and the view is amazing. We would definitely stay here again!"
The price is AED 937
AED 2,298 total
includes taxes & fees
28 Apr - 29 Apr
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
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.
Don't see what you're looking for?
See all available properties in Middleton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middleton

The Revolution Hotel
Premium bedding, down comforters, pillowtop beds, in-room safe

The Revolution Hotel

3.5 star property
8.8 out of 10, Excellent, (1988)
"Loved this hotel! Super clean, quiet, and full of style. Shared bathrooms were spotless and cleaned often. Perfect location—walking distance to historic sites and great restaurants. Only downside: no on-site parking; the nearest garage is a few blocks away. Would definitely stay again!"
The price is AED 496
AED 578 total
includes taxes & fees
13 Apr - 14 Apr
The Revolution Hotel
Harborside Inn Of Boston
Front of property

Harborside Inn Of Boston

4.0 star property
9.2 out of 10, Wonderful, (5017)
"Friendly and helpful staff. Good restaurant attached to it. Super convenient to TStop! Unique to property is you get actual keys to your room and has a VCR /DVD in your room!"
The price is AED 657
AED 766 total
includes taxes & fees
13 Apr - 14 Apr
Harborside Inn Of Boston
citizenM Boston Back Bay
Exterior

citizenM Boston Back Bay

4.0 star property
9.4 out of 10, Exceptional, (980)
"Very cute and high tech hotel "
The price is AED 639
AED 744 total
includes taxes & fees
13 Apr - 14 Apr
citizenM Boston Back Bay
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.