Photo by Ed Gaffny

Search Holiday Rentals 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

Top Holiday Rentals in Chestnut Hill

Sonder 907 Main
Interior

Sonder 907 Main

4.0 star property
8.2 out of 10, Very good, (411)
"Excellent place for the price, just wish that was a USB or outlet with easy access by the bed but besides that I loved. "
The price is ₹11,018
₹12,775 total
includes taxes & fees
30 Jan - 31 Jan
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, (158)
"Great stay. "
The price is ₹9,258
₹19,018 total
includes taxes & fees
20 Jan - 21 Jan
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, (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 ₹8,718
₹14,736 total
includes taxes & fees
22 Jan - 23 Jan
Temple Place Suites
Global Luxury Suites Downtown Boston
Lobby lounge

Global Luxury Suites Downtown Boston

4.0 star property
8.0 out of 10, Very good, (518)
"“I had an absolutely wonderful stay! The property was immaculately clean, beautifully decorated, and thoughtfully equipped with everything I needed. The location was perfect—close to local attractions but still peaceful and quiet. I genuinely couldn’t have asked for a better experience and would highly recommend this place to anyone looking for a relaxing and memorable getaway. I’ll definitely be returning in the future!”"
The price is ₹7,647
₹19,181 total
includes taxes & fees
13 Jan - 14 Jan
Global Luxury Suites Downtown Boston
Bay Village Suites
Desk, laptop workspace, free WiFi, bed sheets

Bay Village Suites

2.0 star property
6.4 out of 10, (141)
"My stay at the Bay Village Hotel in Boston was amazing. To be honest, it was my first experience staying in a self-serving hotel like this. However, everything was good. No one disturbed me, and every time, the hotel was quiet like I was alone in the entire building, and it was convenient. "
Bay Village Suites
No. 284 powered by Sonder
Exterior

No. 284 powered by Sonder

4.0 star property
9.4 out of 10, Exceptional, (855)
"The property was easy to get in and out of and close to many shops and restaurants"
The price is ₹11,877
₹14,009 total
includes taxes & fees
2 Feb - 3 Feb
No. 284 powered by Sonder
Sonder at Pierce Boston
42-inch flat-screen TV with digital channels, TV, streaming services

Sonder at Pierce Boston

4.0 star property
8.8 out of 10, Excellent, (210)
"Fantastic, Pierce-Sonder is always our first choice while visiting Boston. We come often for treatment at Dana Farber Cancer Institute. "
The price is ₹12,731
₹15,016 total
includes taxes & fees
8 Feb - 9 Feb
Sonder at Pierce Boston
Premier Suites - Bay Village
Iron/ironing board, free WiFi, bed sheets

Premier Suites - Bay Village

2.0 star property
6.2 out of 10, (138)
"Definitely not the cleanest place I’ve stayed in. Amenities were okay and the area was close enough to great places that it didn’t really matter. "
Premier Suites - Bay Village
Maverick Suites at 89 Marion
Interior entrance

Maverick Suites at 89 Marion

2.0 star property
8.4 out of 10, Very good, (205)
"Great hotel for the price and location. Would have love to know where we can park in the area. "
The price is ₹8,229
₹16,852 total
includes taxes & fees
9 Jan - 10 Jan
Maverick Suites at 89 Marion
Maverick Suites at 245 Newbury St
Exterior

Maverick Suites at 245 Newbury St

2.0 star property
8.2 out of 10, Very good, (115)
"The only thing stopping me from giving an excelent rating is the room was too hot and had to prop open a heavy window, the blower ran constantly even after turning rhe thermostat down, otherwise the room was perfect in everyway possible."
The price is ₹9,258
₹18,525 total
includes taxes & fees
9 Jan - 10 Jan
Maverick Suites at 245 Newbury St
Maverick Suites at 40 Temple St
Front of property

Maverick Suites at 40 Temple St

2.0 star property
7.6 out of 10, Good, (71)
"Beacon Hill is a good central location and about 30 minutes walk to the Convention Center. There’s a Whole Foods nearby for groceries. My room was small but fine for one person. Check in and out was easy. My only complaint was that there was no way to adjust the fan speed on the climate control and it was noidy but this was not a dealbreaker. "
The price is ₹9,772
₹19,116 total
includes taxes & fees
9 Jan - 10 Jan
Maverick Suites at 40 Temple St
Global Luxury Suites East Boston
Rooftop terrace

Global Luxury Suites East Boston

4.0 star property
7.0 out of 10, Good, (124)
"Good stay. No problems. Just need to work on communication before the stay and maybe get a 24 hr desk. Lovely apartment though and very clean. Lovely neighbourhood and right by the pier. Would love to come back "
The price is ₹10,497
₹21,932 total
includes taxes & fees
13 Jan - 14 Jan
Global Luxury Suites East Boston
Crescent Suites Hotel
Property grounds

Crescent Suites Hotel

3.0 star property
9.6 out of 10, Exceptional, (958)
"Parking easily available, short walk to restaurants. Property is clean, quiet, and the rooms are warm and friendly."
The price is ₹14,487
₹16,182 total
includes taxes & fees
9 Jan - 10 Jan
Crescent Suites Hotel
Maverick Suites at 400 Columbus Ave
Iron/ironing board, free WiFi

Maverick Suites at 400 Columbus Ave

2.0 star property
7.6 out of 10, Good, (96)
"Having to have cleaning of the room as an extra charge should be noted clearly for any future occupants. The unit is not close to any restaurant or store unless you want to walk 10 minutes to get there and carry anything back. It is not convenient to anything of note. Would not stay there again. It was clean but that's the best I could say for the property. "
The price is ₹8,744
₹17,934 total
includes taxes & fees
9 Jan - 10 Jan
Maverick Suites at 400 Columbus Ave
Maverick Suites at 402 Columbus Ave
Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels

Maverick Suites at 402 Columbus Ave

2.5 star property
7.8 out of 10, Good, (50)
"Great location & clean property. Delivers the promise."
The price is ₹8,744
₹17,934 total
includes taxes & fees
19 Jan - 20 Jan
Maverick Suites at 402 Columbus Ave
Charlesgate Suites
Apartment | Premium bedding, desk, iron/ironing board, free WiFi

Charlesgate Suites

3.5 star property
9.4 out of 10, Exceptional, (171)
"Great space, great location. Just as advertised. Oct 2024 EVERYTHING looked new…floors, appliances, paint, furniture. Everything. Everything worked well ( though the fireplace would only stay lit for 5 minutes. Exactly FIVE). Communication was awesome. Prompt and helpful. Only criticism: did not know that there was NO ELEVATOR until the day of check in. At 61 with bad knees and four bags, getting settled in was a major hassle. Four narrow flights of winding stairs. Other than...
Charlesgate Suites
Sonder The Magnolia
Suite, 1 Double Bed, Accessible | 1 bedroom, individually decorated, individually furnished

Sonder The Magnolia

3.5 star property
8.8 out of 10, Excellent, (50)
"Sensational location "
The price is ₹14,329
₹16,901 total
includes taxes & fees
20 Jan - 21 Jan
Sonder The Magnolia
Sonder The Hancock
Individually furnished, iron/ironing board, free cots/infant beds

Sonder The Hancock

3.5 star property
7.8 out of 10, Good, (85)
"Nestled in the Government sector of town. Beautiful historical buildings and streets. Easy walk to most everywhere. "
The price is ₹13,307
₹15,696 total
includes taxes & fees
3 Feb - 4 Feb
Sonder The Hancock
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 types of properties in Chestnut Hill you may be interested in

Omni Boston Hotel at the Seaport
Premium bedding, down duvets, pillow-top beds, minibar

Omni Boston Hotel at the Seaport

4.0 star property
9.2 out of 10, Wonderful, (3105)
"People are so nice"
The price is ₹11,247
₹16,092 total
includes taxes & fees
25 Jan - 26 Jan
Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza
3 bars/lounges

Hilton Boston Park Plaza

4.0 star property
8.4 out of 10, Very good, (3275)
"Centrally located. Clean and comfortable. "
The price is ₹8,846
₹13,795 total
includes taxes & fees
19 Jan - 20 Jan
Hilton Boston Park Plaza
The Dagny Boston
Interior detail

The Dagny Boston

4.0 star property
9.4 out of 10, Exceptional, (5216)
"Excellent "
The price is ₹13,630
₹18,367 total
includes taxes & fees
9 Jan - 10 Jan
The Dagny Boston
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.

Frequently asked questions

Can I find a holiday rental in Chestnut Hill?

Yes, there are holiday rentals close to the most popular sights in Chestnut Hill, or you can select a more secluded option if you're looking for a relaxing stay. 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.

How many holiday rentals will I find in Chestnut Hill?

Choose from 5 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. Boston Common and Fenway Park 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.