
Holiday rentals in Brookline
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Top-rated holiday rentals in Brookline
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Brookline
Guest favourite

Bungalow in Hull
4.95 out of 5 average rating, 74 reviewsThe Sunset Bay Retreat - Cozy Beach Bungalow
JackieRating, 5 stars3 days ago
Nice location to get to Boston on the ferry and still have beach access. The space was perfect for our needs- 3 beds that each sleep 2, also a couch with a lounge section. Nice spacious common room and very functional kitchen.
Superhost

Home in Lakeside Marblehead
4.75 out of 5 average rating, 166 reviewsWalk to Everything Great about Marblehead!
RoryRating, 5 stars5 months ago
We loved our stay at this property. The house is much more historic and lived in, if you are after a pristine and modern stay, this might not be the place for you. But the house more than made up for it in character and cozy vibes, and it fit in perfectly in the charming historic neighborhood in Marblehead. The area has a lot of wonderful spots you can walk to, and the host provided historical information about the area and the house as well! We were so grateful for John’s proactive communication, we didn’t have any issues but I’m confident if we had he would have quickly resolved them! Overall my family had a wonderful weekend and we spent the drive home saying home much we’d love to make another trip in the summer to enjoy the ocean more!! Thanks John for a memorable weekend!
Guest favourite

Home in Wakefield
4.92 out of 5 average rating, 12 reviews60 Jordan-New Construction Townhome
DanaRating, 5 stars3 months ago
Ended up with this host for a last minute booking after another Airbnb host told us last minute there was no heat (in Mass in December?!). Very responsive and professional, this team has very nice locations and fabulous communication all the way through our stay. Would definitely book with them again!
Guest favourite

Flat in East Boston
4.97 out of 5 average rating, 150 reviewsNxt to ocean, 5 min dntwn by T
AndreaRating, 5 stars1 week ago
This place was a great place to stay for our week visit in Boston. The apartment is very conveniently located to the subway, so getting around was very easy, and it was close to the airport as well. It was also very clean and fit the four of us very comfortably. The walls are thin so it’s a little loud with street noise in the front bedroom, but nothing some ear plugs didn’t fix. The TV didn’t really work, but as we were there to explore it didn’t really matter.
Superhost

Flat in Revere
4.5 out of 5 average rating, 4 reviewsCharming 3B2B Condo II Near Beach
MarkRating, 5 stars2 months ago
A nice and clean apartment. We were walking distance to several great restaurants and bars. I would stay again next time I have shows to see in Boston.
Superhost

Flat in Beverly
4.75 out of 5 average rating, 297 reviewsSalem/Beverly- Explore Boston's North Shore!
MichelleRating, 5 stars5 months ago
This place was just perfect for what we needed! It was exactly as described, clean and more than roomy enough for our party. The location is great too. Easily accessible to Salem, stores, restaurants and public transportation. Aurelia left a binder with great suggestions and then checked in with me to make sure we were happy and settled. Highly recommended !
Top guest favourite

Flat in Brighton
4.99 out of 5 average rating, 79 reviewsNew 3 bedroom, 2 bath unit, meadow view!
FionaRating, 5 stars2 weeks ago
Simon’s place has everything you need and more. Fridge stocked with bottled water and sodas. Chocolates, oranges and bars for snacking. Bouquet of fresh flowers in the master bedroom. We felt very welcomed into this wonderful space. It is on the second floor of a 3 level house. Three apartments total in the building. Great to have off street parking. I highly recommend.
Guest favourite

Guest suite in Arlington
4.85 out of 5 average rating, 82 reviews★Modern Studio-Private Entrance,Washer+Dryer★
BrianRating, 5 stars4 months ago
Had a great stay at this place (this was our second time there). Our plane to the area was much delayed but our hosts were understanding and very helpful. Everything was as advertised and the place was convenient to our activities visiting family. Will definitely stay there again!
Quick stats about holiday rentals in Brookline
Total rentals
1.1K properties
Total number of reviews
44K reviews
Family-friendly rentals
410 properties are a good fit for families
Pet-friendly rentals
260 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
530 properties have a dedicated workspace
Destinations to explore
- Boston Holiday rentals
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- Rentals with a firepit Brookline
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- Bed and breakfasts Brookline
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- Hampton Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Brown University
- New England Aquarium
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Onset Beach
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Oakland Beach
- Boston Public Library
- Crane Beach
- Scusset Beach
- Pinehills Golf Club
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market