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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
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Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Milton Vacation Homes

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, (170)
"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
Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean
Interior

Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean

9.4 out of 10, Exceptional, (10)
The price is CA $832
CA $1,139 total
includes taxes & fees
Aug 28 - Aug 29
Luxury 6 BR·7 Beds·4.5 BA house in charming Marblehead & walkable to the ocean
Entire Lower Level of the House, Across From The Beach
Beach

Entire Lower Level of the House, Across From The Beach

9.8 out of 10, Exceptional, (17)
"Loved getting to visit the beach and the short drive to Salem!"
The price is CA $291
CA $514 total
includes taxes & fees
Sep 8 - Sep 9
Entire Lower Level of the House, Across From The Beach
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, (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
TV, offices

Clean, Contemporary Escape Near T

8.8 out of 10, Excellent, (8)
"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
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
Smart TV, video games, computer monitors, printers

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

9.8 out of 10, Exceptional, (64)
"The property is a great place for a family to stay. Plenty of room, well stocked kitchen, a great location in Boston. Highly recommend! "
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
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
Charming 3-bedroom townhome in Marblehead 3 miles to Salem 14 miles to airport
Smart TV, books

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

10.0 out of 10, Exceptional, (6)
"Our family had a fantastic time staying here, would love to stay here again. "
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
Exterior detail

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

8.8 out of 10, Excellent, (29)
"Location is good and the host is easy to reach and communicate with. Needs a couple of minor improvements:1. AC in the main floor BR & LR.2. Include wash cloths and upgrade towels.3. Add shade on skylight on top floor BR. "
The price is CA $436
CA $824 total
includes taxes & fees
Aug 25 - Aug 26
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.
3 bedrooms, desk, iron/ironing board, WiFi

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!!"
The price is CA $342
CA $703 total
includes taxes & fees
Aug 24 - Aug 25
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.
Boston's Best Vacation Home
Exterior

Boston's Best Vacation Home

9.8 out of 10, Exceptional, (58)
"Great location easy to get to all of Boston, clean and well maintained, large kitchen and living room. Enjoyed our stay"
Boston's Best Vacation Home
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!
Fishing

CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!

2.0 star property
9.4 out of 10, Exceptional, (26)
"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!"
The price is CA $275
CA $742 total
includes taxes & fees
Sep 14 - Sep 15
CityScape: Urban Convenience Meets Affordability in this Modern City Living in the Heart of Chelsea!
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Marina

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

9.6 out of 10, Exceptional, (87)
"Easy and fast communication with host, was a great stay."
The price is CA $555
CA $1,024 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Seaside Sanctuary in Historic Marblehead
Marina

Seaside Sanctuary in Historic Marblehead

Seaside Sanctuary in Historic Marblehead
Beautifully Renovated Cozy Home
Private kitchen

Beautifully Renovated Cozy Home

Beautifully Renovated Cozy Home
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Terrace/patio

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

10.0 out of 10, Exceptional, (20)
"We had such a phenomenal experience at this rental. The owners were more than accommodating and made the stay so much more enjoyable!! "
The price is CA $431
CA $680 total
includes taxes & fees
Sep 9 - Sep 10
Bright & Stylish Coastal Retreat in Marblehead Historic Center w Parking!
Boston's Beach Home: Pool, 1min to Beach, Pet +
Fridge, microwave, oven, stovetop

Boston's Beach Home: Pool, 1min to Beach, Pet +

9.8 out of 10, Exceptional, (7)
"Great house in a centrally located area. House was cozy and steps from the beach. We highly recommend this place. "
Boston's Beach Home: Pool, 1min to Beach, Pet +
Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching
Exterior

Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching

10.0 out of 10, Exceptional, (7)
"My extended family stayed at this beautiful home over the weekend and thoroughly enjoyed it! It was an easy check-in process, and the communication with the owner was simple. The house is just gorgeous, with lovely views of the Mystic Lakes. We had terrible weather while we were staying here, so we didn't get to enjoy the access to the water, but... next time!"
Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching
Cape cod style seaside condo Boston, Airport,Train
Terrace/patio

Cape cod style seaside condo Boston, Airport,Train

9.4 out of 10, Exceptional, (8)
"Property and owners were top notch. Views were amazing"
Cape cod style seaside condo Boston, Airport,Train
Pet-Friendly Marblehead Home Near Preston Beach!
Fridge, microwave, stovetop, coffee/tea maker

Pet-Friendly Marblehead Home Near Preston Beach!

9.8 out of 10, Exceptional, (13)
"My sisters and myself met up with my cousins for a Cousin's Trip in Salem we loved the location of the house in relation to Salem..it.took us only about 15 or less minutes to get to major attractions withing the city. Thouse was more than spacious, "
Pet-Friendly Marblehead Home Near Preston Beach!
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 Milton Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Close yo everything "
Joni 5-night trip
Posted 2 hours ago
Harborside Inn Of Boston