Photo by Ed Gaffny

Chestnut Hill Vacation Rentals

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Browse Select Chestnut Hill Vacation Homes

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Centrally located in the heart of Boston near T

8.8 out of 10, Excellent, (15)
"Enjoyed this little place so much. Very safe neighborhood! "
The price is CA $252
CA $644 total
includes taxes & fees
Jan 8 - Jan 9
Centrally located in the heart of Boston near T

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

10.0 out of 10, Exceptional, (123)
"The house is located on a quite street near a quaint Downtown Area The house has area for two cars The house was immaculate and very comfortable. The owner Gregg was very welcoming and worked hard to make sure everything was Ok I want to thank him again for letting my family stay in such a beautiful home If you need a place do not hesitate to take this house "
The price is CA $470
CA $829 total
includes taxes & fees
Jan 5 - Jan 6
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

6 bedroom house in a quiet and convenient neighborhood

6.8 out of 10, (3)
"The good, Large House, lots of bedrooms. Felt very safe, nice Alarm system. And the Piano was very fun for a singing and having fun. Reconstruction in process. The bad, the beds, not good, the house is falling apart, scary stairs, the bath rooms are tiny and do not offer shampoo, conditioner, and conditioner. Could not find bath towels. The ugly - mouse droppings all over the kitchen. Mouse found in one bedroom, captured mouse and took outside. Let host know that there was a mouse and mice...
6 bedroom house in a quiet and convenient neighborhood

Harvard House Host Your 2024 Family Gathering In Boston at This Beautiful Venue

9.8 out of 10, Exceptional, (62)
"Once again, we are so appreciative of all the comfortable first-floor spaces to spread out as a family. The kitchen is equipped to produce a fully home-prepared feast—all the utensils, pots, pans, knives, and dishes you might need. The dining room table can comfortably accommodate a very large group. Cozy beds, extra blankets as needed, and loads of towels. The host is very communicative and caring."
Harvard House Host Your 2024 Family Gathering In Boston at This Beautiful Venue

Remodeled Townhouse close to Boston

10.0 out of 10, Exceptional, (23)
"Our family of four enjoyed a very comfortable stay while visiting relatives near Watertown. The beds were comfortable and everything worked well. Our host responded to any questions very promptly. The place is a few minutes’ walking distance to restaurants and a drug store, and a nice walk along the River. It’s near a busy street and was noisy in the weekday morning but earplugs can cover that. Recommended!"
Remodeled Townhouse close to Boston

Newly renovated home, top of the line appliances.

9.8 out of 10, Exceptional, (111)
"We spent Thanksgiving weekend with our adult child at the house, and what a great place it was. The house had everything we needed, including a wonderful kitchen for cooking Thanksgiving dinner. And the price was competitive with what it would have cost for a hotel for just us. We will consider this place for our next Boston visit."
Newly renovated home, top of the line appliances.

MODERN Spacious 4bed 2bath HARVARD MIT BOS Cambridge Somerville walk everywhere!

9.4 out of 10, Exceptional, (44)
"The stay was in suburb of Boston. Good location. There was a few repairs needed. Bathroom sink faucet moved. There was a light in bedroom ceiling that had open wires. Other than that the place was clean. The outside patio could used cleaned up but we didn’t ise"
The price is CA $373
CA $771 total
includes taxes & fees
Jan 7 - Jan 8
MODERN Spacious 4bed 2bath HARVARD MIT BOS Cambridge Somerville walk everywhere!

Norwood Luxe Suite- Pet friendly & Commuter friendly

10.0 out of 10, Exceptional, (7)
"We had additional work to complete in Sharon, MA on a remodel project that we extended another week at Norwood for our team members, which offered them a place to unwind and recharge after long hours working. Norwood is lovely, clean and well-equipped with all the amenities. Susan is such an attentive host, it made for an all around wonderful experience. "
Norwood Luxe Suite- Pet friendly & Commuter friendly

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

10.0 out of 10, Exceptional, (9)
"Wonderdul location. Close to shopping, foxboroigh, restaurants. "
Waterfront Lake house near Gillette Stadium and central to Boston and Providence

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

The price is CA $229
CA $584 total
includes taxes & fees
Jan 8 - Jan 9
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

Peaceful 2Br House in Cambridge

2.0 star property
6.0 out of 10, (4)
"A marvelous place. Parking spot was appeciated!"
Peaceful 2Br House in Cambridge

Luxury Boston Ranch –Sleeps 8|Pet+|Private pool

10.0 out of 10, Exceptional, (1)
"We were in town for a family event and this was a great place for our group! Plenty of room, clean and quiet neighborhood. Definitely recommend! "
Luxury Boston Ranch –Sleeps 8|Pet+|Private pool

Discover Watertown charm near Harvard 6 min drive, Boston 10 mins drive.

10.0 out of 10, Exceptional, (2)
"Our business trip worked out fine in this location about the only thing that is a little unclear is that that says the house sleeps eight but if everyone traveling needs to sleep in individual spaces, it really only sleeps four. All the amenities are excellent and two full bathrooms works out extremely well"
Discover Watertown charm near Harvard 6 min drive, Boston 10 mins drive.

Belmont Home < 3 Mi to Harvard Square!

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is CA $196
CA $407 total
includes taxes & fees
Jan 15 - Jan 16
Belmont Home < 3 Mi to Harvard Square!

Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs

7.0 out of 10, Good, (21)
"It's in a basement and there was a door to another part of the basement that was locked and we could see a light that was on all night on the other side. It was very quiet though, great if you just need somewhere to sleep."
The price is CA $101
CA $177 total
includes taxes & fees
Jan 19 - Jan 20
Brown sugar private one bedroom few minutes away grocery stores, dollar tree,bjs

284-Cozy House with free huge parking

9.8 out of 10, Exceptional, (58)
"Wonderful weekend, close to Boston attractions, comfortable accommodations. "
The price is CA $258
CA $697 total
includes taxes & fees
Jan 8 - Jan 9
284-Cozy House with free huge parking

37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

9.2 out of 10, Wonderful, (25)
"Jenny/host was quick to answer all of my questions The only negative aspect of our stay was due to the street traffic on Copeland. It made it hard to sleep at times"
The price is CA $186
CA $494 total
includes taxes & fees
Jan 15 - Jan 16
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

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

9.4 out of 10, Exceptional, (78)
"Great location and parking"
The price is CA $360
CA $792 total
includes taxes & fees
Jan 7 - Jan 8
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino
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

4.0 star property
8.2 out of 10, Very good, (409)
"Perfect location!"
The price is CA $167
CA $193 total
includes taxes & fees
Jan 30 - Jan 31
Sonder 907 Main

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (158)
"Great stay. "
The price is CA $147
CA $310 total
includes taxes & fees
Jan 12 - Jan 13
Maverick Suites at 28 Fenway

Temple Place Suites

2.5 star property
6.8 out of 10, (176)
"The room was ok. The common kitchen was usually dirty and without enough utensils and cutery. Is difficult to get hot water in the shower, sometimes it is ok and some others it is cold"
The price is CA $146
CA $248 total
includes taxes & fees
Jan 19 - Jan 20
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.