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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 477 Vacation Homes in Chestnut Hill with updated reviews, rates, and availability.

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, (55)
"We truly enjoyed our stay. The house is adorable and located in a beautiful suburban neighbourhoid. It was an excellent home base from which to explore Boston. The host is extremely accommodating and is easily contacted.We would 100% recommend this place as long as you have your own car to get around the city."
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
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)
"Walkable to so many restaurants and transit! Highly recommended!"
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
Exterior detail

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

9.0 out of 10, Wonderful, (28)
"Good place for a stay near Boston."
The price is AED 749
AED 1,682 total
includes taxes & fees
5 May - 6 May
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Interior

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

10.0 out of 10, Exceptional, (69)
"House is awesome, team is easy to work with. it was a perfect stay. "
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
Entire Home 2BR 2BTH Quite Area with parking
Fridge, microwave, oven, stovetop

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)
"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
Belmont Home < 3 Mi to Harvard Square!
Interior

Belmont Home < 3 Mi to Harvard Square!

2.0 star property
10.0 out of 10, Exceptional, (7)
"Nice place"
The price is AED 702
AED 1,235 total
includes taxes & fees
26 May - 27 May
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, (77)
"We loved this house, it was very clean and cozy. Nicely decorated. Kitchen had everything you need. We really enjoyed it."
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, (13)
"Comfortably accommodated our family of 5. Very cool bedroom behind a bookshelf! Would recommend."
The price is AED 999
AED 2,349 total
includes taxes & fees
4 May - 5 May
Enchanting Hidden Door Escape
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Beach

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

2.0 star property
9.4 out of 10, Exceptional, (18)
"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 AED 1,028
AED 2,465 total
includes taxes & fees
30 May - 31 May
CityScape: Sleek Urban Oasis; Parking, Near: Boston, Casino, Airport, Parks, Hospitals, Buses
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Aerial view

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

9.2 out of 10, Wonderful, (25)
"Came to Boston for a few sporting events and the VRBO was optimally located to get us to all hot spots with minimal delay. Very clean and inviting place. "
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem
Charming home with deck- walkable to transit, shops & restaurants
Fridge, microwave, oven, stovetop

Charming home with deck- walkable to transit, shops & restaurants

10.0 out of 10, Exceptional, (2)
"Everything was great! Our host was very quick to respond if there was a question. Plenty of room for all 5 adults (and then some). The only negative about the location is pulling out of the driveway. Easy enough to deal with though. For us, the proximity of this location to our family and friends for this visit was great. 20-25 minutes at most whether going into Boston or heading out to family in the suburbs."
Charming home with deck- walkable to transit, shops & restaurants
Hidden Gem right in the city of Boston!
Interior

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (19)
"We had a wonderful stay. The apartment was exactly as advertised. It’s very clean and in a cute borough with some great restaurants and shops and any other convenience you might need. The apartment has a large kitchen that’s great for cooking your own meals if you wish to do so. Check in was completely seamless even though we were arriving late at night. "
Hidden Gem right in the city of Boston!
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
TV, offices, computer monitors

Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

10.0 out of 10, Exceptional, (13)
"Home exactly as advertised. Nice place to stay. "
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
Bright Boston House | near T
Fridge, microwave, oven, stovetop

Bright Boston House | near T

9.6 out of 10, Exceptional, (5)
Bright Boston House | near T
Union Square House
Outdoor dining

Union Square House

9.6 out of 10, Exceptional, (67)
"Very convenient for getting off the transit and fun area to wander around! House was easy to check into and very clean!"
Union Square House
37 - 3BR - Quincy Cozy Townhouse near Blue Hills
Fridge, microwave, oven, stovetop

37 - 3BR - Quincy Cozy Townhouse near Blue Hills

9.0 out of 10, Wonderful, (28)
"We were here for a performance at Boston Symphony Hall and it was nice and away from the crazy of the city."
The price is AED 511
AED 1,284 total
includes taxes & fees
4 May - 5 May
37 - 3BR - Quincy Cozy Townhouse near Blue Hills
Waterfront Lake house near Gillette Stadium and central to Boston and Providence
Property grounds

Waterfront Lake house near Gillette Stadium and central to Boston and Providence

10.0 out of 10, Exceptional, (14)
"Great location with all the amenities to make for a memorable weekend with friends!"
Waterfront Lake house near Gillette Stadium and central to Boston and Providence
Historic house renovated for modern convenience
Exterior detail

Historic house renovated for modern convenience

9.8 out of 10, Exceptional, (121)
"Really great location and the right size for our group! We had a great time"
Historic house renovated for modern convenience
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 Chestnut Hill

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (470)
"The location was great. Close to the metro and good dining options. "
The price is AED 554
AED 643 total
includes taxes & fees
26 May - 27 May
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Living area | 50-inch Smart TV with satellite channels, Netflix, Hulu

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (192)
"Amazing stay, thank you!"
The price is AED 437
AED 861 total
includes taxes & fees
5 May - 6 May
Maverick Suites at 28 Fenway
Temple Place Suites
Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets

Temple Place Suites

2.5 star property
6.8 out of 10, (199)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is AED 437
AED 704 total
includes taxes & fees
4 May - 5 May
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.