Photo by Ed Gaffny

Search Vacation Homes in Chestnut Hill

  • 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
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 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, (53)
"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
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, (159)
"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
15 Apr - 16 Apr
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
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, (68)
"We had a great stay in the Bayside Jewel. The owner was courteous, available and so helpful! The property is exactly as advertised, fully stocked, and so comfy for our group of 5 adults, one toddler and one infant. The location was convenient for our needs. The garage was a stellar asset and large enough to fit our Grand Wagonerr! We highly recommend this property, its owners and managers!!! Our only disappointment in our trip was the weather. We came a but too early seasonally and the rain all...
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
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
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 974 total
includes taxes & fees
16 Apr - 17 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, (12)
"Would stay again"
The price is AED 956
AED 2,296 total
includes taxes & fees
15 Apr - 16 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
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
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, (1)
"My family and I were in town to tour Boston College because our son starts there in the fall and we wanted to stay near the school and get the feel of the neighborhood. The home was in a perfect location and great neighborhood. We were only a few minutes from the college and about 20 minutes from downtown Boston. The host was great with recommendations to stores and restaurants both near the home and downtown. I would definitely stay here again. Also, I drive a big truck so off street parking...
Charming home with deck- walkable to transit, shops & restaurants
Hidden Gem right in the city of Boston!
Smart TV

Hidden Gem right in the city of Boston!

9.8 out of 10, Exceptional, (19)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
The price is AED 529
AED 1,516 total
includes taxes & fees
26 Apr - 27 Apr
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)
"The home is well cared for and beautiful. The beds were very comfortable. It was the perfect spot for our family getaway, very close to Boston. Would stay here again in a heartbeat if we are ever in the area again!"
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths
Bright Boston House | near T
Fridge, microwave, oven, stovetop

Bright Boston House | near T

10.0 out of 10, Exceptional, (2)
"Jay was absolutely amazing and responded to all of my texts right away, communication was seamless, and the property was beautiful!"
Bright Boston House | near T
Union Square House
3 bedrooms, desk, free WiFi, bed sheets

Union Square House

9.6 out of 10, Exceptional, (68)
"Good vibe, comfy stay, fine location. No complaints. Host was responsive and on top of the care of the place."
Union Square House
37 - Quincy Warm & Cozy Home for a Perfect Stay
Fridge, microwave, oven, stovetop

37 - Quincy Warm & Cozy Home for a Perfect Stay

9.0 out of 10, Wonderful, (27)
"This was a great stay in a great location. Unit was clean and the mananger was courteous and very responsive"
The price is AED 474
AED 1,235 total
includes taxes & fees
16 Apr - 17 Apr
37 - Quincy Warm & Cozy Home for a Perfect Stay
Waterfront Lake house near Gillette Stadium and central to Boston and Providence
Smart TV, fireplace, video games, table tennis

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

10.0 out of 10, Exceptional, (11)
"Thank you so much for allowing us a great weekend at your place. It was perfect for our group. Loved being able to have morning coffee overlooking the water. The house is decorated with modern touches and feels like home. We will definitely reach back out. "
Waterfront Lake house near Gillette Stadium and central to Boston and Providence
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 Chestnut Hill
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 Chestnut Hill

Sonder 907 Main
Lobby

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (456)
"Fair price, good environment."
The price is AED 768
AED 891 total
includes taxes & fees
22 Apr - 23 Apr
Sonder 907 Main
Maverick Suites at 28 Fenway
Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (182)
"Clean, as pictured, updated. "
The price is AED 375
AED 790 total
includes taxes & fees
22 Apr - 23 Apr
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, (196)
"We loved how walkable this location was! It was easy to walk or find public transport for anywhere we needed! "
The price is AED 436
AED 704 total
includes taxes & fees
27 Apr - 28 Apr
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.