Photo by Ed Gaffny

Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
10.0 out of 10, Exceptional, (188)
"Wonderful room on a houseboat. Easy access to a short inexpensive ferry to Boston. This was a unique experience and Green Turtle was fabulous!"
The price is HK$2,926
per night
21 May - 22 May
"Travelers' Choice Award" Green Turtle I Houseboat in Boston Harbor!
Interior
Capricornus: Oceanside Vacation
10.0 out of 10, Exceptional, (2)
"We stayed on a houseboat in Lewis Wharf a few years ago and loved it, so we wanted to donit again. We are actually’local’ and my teen and adult kids like to stay in the city for short breaks. (We live an hour away). Love the proximity to the North End, the T, the Aquarium etc. Surprisingly quiet. We miss the boat we used to have, so we enjoy getting gently rocked to sleep. Will always choose a houseboat over a hotel if it’s available."
The price is HK$2,746
per night
17 Jun - 18 Jun
Capricornus: Oceanside Vacation
Dining
Fantastic 2 Bedroom Apartment Near Downtown
9.8 out of 10, Exceptional, (89)
"Very pleasant. Roomy, clean, well equipped. Neighborhood somewhat run down. On south side of city while tourist sites are on North side. We used Uber a lot. Overall nice stay. Thank you."
Fantastic 2 Bedroom Apartment Near Downtown
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Pool
Beautiful Retreat close to Downtown Boston. Pets friendly.
9.8 out of 10, Exceptional, (82)
"Everything was just as David had stated on the website, and he was very responsive to initial inquiries when booking and also upon arrival. Plenty of towels, and though we didn't need, there were extra toiletries in the event you forgot something. Bed was very comfortable and apartment was clean."
The price is HK$983
per night
21 May - 22 May
Beautiful Retreat close to Downtown Boston. Pets friendly.
Interior
Boston's Finest New Renovated Apartment
9.8 out of 10, Exceptional, (22)
"The property worked out well for us and Cutis was a very helpful and gracious host. Everything worked out fine for us and we appreciated his helpfulness"
Boston's Finest New Renovated Apartment
Marina
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
9.8 out of 10, Exceptional, (160)
"My son and I stayed here on a spring break trip. The location was a 5 min walk from the USS Constitution, a 10 min walk to Bunker Hill and a 20-30 min walk to the North End. However because we were on a boat in a marina there was zero traffic noise and that combined with the rocking motion of the houseboat meant I slept extremely well. Bonus: we were visited on several days by a pair of ducks who would hang out on the patio with us. Got to love a vacation home that comes with pets! Downsides?...
The price is HK$1,560
per night
6 Jun - 7 Jun
Houseboat in Boston Harbor Wifi A/C /Heat Be rocked to sleep
Living area
28 Fenway
2.0 star property
9.6 out of 10, Exceptional, (49)
"Cozy accommodations close to Back Bay and Fenway. A little too cozy for a couple - better for a solo leisure stay (no desk or working space). Rooms in pics look bigger than what it actually is. Garden level rooms will be a bit noisy. Excellent location and spotless and good security. "
28 Fenway
Property grounds
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (827)
"Our quick one night stay was great! Dana was very helpful at check in- a map of all the walkable restaurants for dinner and a recommendation for breakfast. The room was clean and the bed was comfortable. Would definitely stay here again."
The price is HK$1,397
per night
27 May - 28 May
Crescent Suites Hotel
Premium bedding, desk, iron/ironing board, free WiFi
Charlesgate Suites
3.5 star property
9.6 out of 10, Exceptional, (143)
"Great location, walking distance to Fenway. Very pleasant experience, would highly recommend."
Charlesgate Suites
Interior
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
9.6 out of 10, Exceptional, (124)
"It was everything we thought as far as location in the boat itself, but the exterior of the boat was in need of a cleaning the bathtowels. What didn't you and mildew smelling the betting was tingy. And a little smelly, but overall, the place was clean in general. And had everything you'd want or need."
Boston Harbor Yacht, AC/Heat, Walk to North End WiFi
Fridge, microwave, coffee/tea maker, toaster
Boston's Most Charming Bed & Breakfast - Heart of the City
9.6 out of 10, Exceptional, (97)
"Great property. Great location. Great owner and great / fast communicaton."
Boston's Most Charming Bed & Breakfast - Heart of the City
TV, DVD player, books, music library
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
9.6 out of 10, Exceptional, (132)
"Good location. Easy communications with host. Easy entrance and exit procedures."
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
Exterior
No. 284 powered by Sonder
4.0 star property
9.4 out of 10, Exceptional, (778)
"I used No 284 powered by Sonder as I was attending a conference in the Hynes conference center this week. The location is perfect and very close to the conference center and prudential shopping center, with plenty of great food and drink options close by. The room was spotless and very convenient with touchless check in and entry via an app. For the cost of the room, I would have expected a bit more space, but it is prime real estate in central Boston... All in all, great experience, would go...
The price is HK$1,936
per night
27 May - 28 May
No. 284 powered by Sonder
Courtyard
HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2204)
"Very clean and comfortable "
The price is HK$1,240
per night
26 May - 27 May
HYATT house Boston/Burlington
Fridge, microwave, oven, stovetop
Beautiful, Cozy Ultra Convenient Salem Home
9.2 out of 10, Wonderful, (7)
"Convenient to dowtown"
The price is HK$1,638
per night
3 Jun - 4 Jun
Beautiful, Cozy Ultra Convenient Salem Home
1 bedroom, individually decorated, individually furnished
Sonder The Magnolia
3.5 star property
9.0 out of 10, Wonderful, (32)
"The room/unit we were in was above shake shack so you could here the music and noise from the restaurant. Location was great for us though it was Midway between fenway and Boston common in back bay. We took the free logan express bus to back bay and the room was 1 block away. Only $3 to go back to the airport. "
The price is HK$2,451
per night
23 May - 24 May
Sonder The Magnolia
Interior
90-Boston Spacious Convenient Apartment
9.0 out of 10, Wonderful, (24)
"We had a wonderful stay! The view from the kitchen window is amazing! Very convenient location. We were able to walk for groceries, dining and entertainment. Would definitely recommend. It was spacious and very cozy."
The price is HK$1,943
per night
6 Jun - 7 Jun
90-Boston Spacious Convenient Apartment
Living area
Sonder at Pierce Boston
4.0 star property
8.8 out of 10, Excellent, (171)
"The Pierce was awesome! Beautiful views from the room, great location to go see a Sox game, super clean and great staff!!! I can’t say enough good things about it, if I go back to Boston, this is where I’m staying no question. "
The price is HK$2,405
per night
16 Jun - 17 Jun
Sonder at Pierce Boston
Interior
Sonder 907 Main
4.0 star property
8.2 out of 10, Very good, (335)
"2.5km Walk to Fenway, lost of shopping and dining near by, the best is that each room has individual wifi! So no sharing. Very safe area around MIT "
The price is HK$1,870
per night
16 Jun - 17 Jun
Sonder 907 Main
Front of property
89 Marion
2.0 star property
8.2 out of 10, Very good, (132)
"Quiet, safe and great location near Fenway Park. Will come back. "
The price is HK$1,287
per night
27 May - 28 May
89 Marion
Don't see what you're looking for?
See all available properties in Chestnut Hill
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.

Other types of properties in Chestnut Hill you may be interested in

Exterior
Seaport Hotel Boston
4.0 star property
9.6 out of 10, Exceptional, (2156)
"Great location!"
The price is HK$2,099
per night
23 May - 24 May
Seaport Hotel Boston
Interior detail
The Dagny Boston
4.0 star property
9.2 out of 10, Wonderful, (3512)
"I had travel issues getting to the hotel, but the team looked after my son who was meeting me there. I cannot thank the team enough for that! Great service and lovely room."
The price is HK$1,607
per night
27 May - 28 May
The Dagny Boston
Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2053)
"The staff was friendly. Our room was super clean, comfy, and had a great view of the city. I loved the floor to ceiling windows. "
The price is HK$1,397
per night
27 May - 28 May
Omni Boston Hotel at the Seaport
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.

Search for holiday rentals in Chestnut Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestnut Hill using one of the methods below:

  • View our selection of featured holiday rentals in Chestnut Hill
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  • Enter your travel dates to view the best deals on holiday rentals in Chestnut Hill while they last

Look no further and take a look at our great range of rental properties in Chestnut Hill!

Frequently asked questions

Can I find a holiday rental in Chestnut Hill?

Yes, you can find holiday rentals where you'll be only 6.4 mi (10.4 km) from New England Aquarium, offering you a more secluded option if you want peace and quiet. Chestnut Hill is known for its university setting and football games. Make sure you have time to check out the restaurants and forests during your trip.

What are some of the best holiday rentals that Chestnut Hill has to offer?

Beautiful, Cozy Ultra Convenient Salem Home: This holiday home rental outside of Chestnut Hill is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Chestnut Hill?

Choose from 4 Expedia holiday rentals in Chestnut Hill for a memorable holiday.

What’s there to see and do in Chestnut Hill?

Cultural attractions include McMullen Museum, whereas Chestnut Hill Reservoir is a spot to enjoy nature. Fenway Park and TD Garden are other popular places to visit in the area.

What’s a holiday rental in Chestnut Hill like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Hill. Holiday rentals offer amenities such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.

Recent reviews of Chestnut Hill properties
Expedia verified reviews

The Godfrey Hotel Boston

The Godfrey Hotel Boston

5/5 Excellent
"Beautiful hotel . Wish they had a place for breakfast . Coffe shop attached was limited"
A verified traveller stayed at The Godfrey Hotel Boston
Posted 2 days ago
The Godfrey Hotel Boston