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Check prices for these dates

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

Compare 152 Condo Rentals in Chestnut Hill with updated reviews, rates, and availability.

The Heart of Southie (Garage + Roof Deck)
View from property

The Heart of Southie (Garage + Roof Deck)

10.0 out of 10, Exceptional, (19)
"This property was exactly what expected. Will book again next time we visit Boston."
The Heart of Southie (Garage + Roof Deck)
Modern 2br with W/D in unit, Parking, central air
Fridge, microwave, oven, stovetop

Modern 2br with W/D in unit, Parking, central air

10.0 out of 10, Exceptional, (42)
"Very very clean well stocked all the co Fort of home "
Modern 2br with W/D in unit, Parking, central air
🎖The Boiler Room - Close to Subway & Downtown🎖
Interior

🎖The Boiler Room - Close to Subway & Downtown🎖

9.8 out of 10, Exceptional, (68)
"Stayed in The Boiler Room downstairs. Ceiling is a bit creaky, could use a grab bar for entering/exiting shower. Otherwise a good place to stay. Transit train is only a 10 min walk, and several restaurants nearby. We recommend Molinari's"
🎖The Boiler Room - Close to Subway & Downtown🎖
Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry
Fridge, microwave, oven, stovetop

Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry

8.8 out of 10, Excellent, (3)
"Great location, away from hustle and bustle, but still just a few train stops away. Property is nice, clean and modern. "
The price is $330
includes taxes & fees
$287 per night
May 1 - May 2
Charming 2-bedroom condo minutes from airport Boston with WiFi, AC, and laundry
Right Near Convention Center and Train Station
Fridge, microwave, oven, stovetop

Right Near Convention Center and Train Station

4.0 star property
10.0 out of 10, Exceptional, (11)
"The apartment is nice and all you need is there. Good location."
Right Near Convention Center and Train Station
🎖The Ashmont Suite - Close to Subway + Downtown🎖
Fridge, microwave, oven, stovetop

🎖The Ashmont Suite - Close to Subway + Downtown🎖

10.0 out of 10, Exceptional, (41)
"The Ashmont Suite was accurately described. It was in a quiet older neighborhood. The home was clean, well appointed and truly had every thing we needed. Communication from the owner was timely and clear. We stayed as a family as our son was running the Boston Marathon. The property was about a 20 minute Uber to the airport and downtown area. We thoroughly enjoyed our stay and would absolutely recommend it to others."
The price is $459
includes taxes & fees
$399 per night
May 13 - May 14
🎖The Ashmont Suite - Close to Subway + Downtown🎖
3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D
Fridge, microwave, oven, stovetop

3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D

10.0 out of 10, Exceptional, (8)
"Spacious, clean, and well-equipped home, nice walks through the neighborhood and to nearby waterfront parks. Responsive and helpful hosts. Easy drive to local attractions as well as Boston and Cambridge. Would stay there again. "
3 Bed Moreland St · Stunning 3+BD Under 10 mins to BOS w/parking & W/D
Excellent 2 bedroom condo in South Boston
Miscellaneous

Excellent 2 bedroom condo in South Boston

10.0 out of 10, Exceptional, (19)
"Exactly as advertised / nice place. Really close to the subway, so everything in Boston is accessible!!!"
Excellent 2 bedroom condo in South Boston
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
TV, DVD player, books, music library

LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo

9.6 out of 10, Exceptional, (159)
"Nice enough. Has Access to roof area. Good kitchen. Lots of choices to eat nearby "
LOCATION, LOCATION LOCATION, 2 Bed, 2 Bath Luxury Condo
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
Exterior

Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem

2.0 star property
8.6 out of 10, Excellent, (4)
"We just needed a night to stay between flights. Unit was spacious, 2 beds, and inflatable mattress that was super comfy. We all haad our own private "corner""
The price is $228
includes taxes & fees
$204 per night
May 5 - May 6
Ultra Cozy Ultra Convenient 2 Bedroom Condo convenient to all of Salem
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Fridge, microwave, oven, stovetop

Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem

10.0 out of 10, Exceptional, (4)
"Very nice and well situated haven close to historic Salem.Comfy and cosy with witchy theme well done!We had a great stay!"
The price is $338
includes taxes & fees
$303 per night
May 1 - May 2
Ravens Hollow- Enchanting 2-bedroom condo Near Downtown Salem
Le Elona – Private Guest Suite on a Scenic Estate
Terrace/patio

Le Elona – Private Guest Suite on a Scenic Estate

The price is $351
includes taxes & fees
$327 per night
May 1 - May 2
Le Elona – Private Guest Suite on a Scenic Estate
Downtown Salem - Park & Play Modern 3 Bedroom
Interior

Downtown Salem - Park & Play Modern 3 Bedroom

10.0 out of 10, Exceptional, (42)
"The house was very cute and spacious for my family trip. The location was great as well. "
The price is $428
includes taxes & fees
$383 per night
May 4 - May 5
Downtown Salem - Park & Play Modern 3 Bedroom
Lg Suite for up to 8 ppl/1 floor
Terrace/patio

Lg Suite for up to 8 ppl/1 floor

9.4 out of 10, Exceptional, (12)
"Great place! Plenty of room, clean, and well kept. Very close to a ton of stuff to see and do. Highly recommend!"
The price is $401
includes taxes & fees
$349 per night
May 11 - May 12
Lg Suite for up to 8 ppl/1 floor
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
Fridge, microwave, oven, stovetop

Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston

8.6 out of 10, Excellent, (145)
"The apartment was very clean and in an excellent location."
Historic Beacon Hill Duplex -2 bed 1.5 bathrooms Condo -heart of Boston
Stylish, Comfortable Luxury | Near T
Fridge, microwave, oven, stovetop

Stylish, Comfortable Luxury | Near T

9.0 out of 10, Wonderful, (2)
"Stayed here with three other adults for a weekend stay, enjoying Boston. The beds were comfortable, the kitchen was well equipped and the place was sunny and bright. "
Stylish, Comfortable Luxury | Near T
Boston Apartment | near T
Miscellaneous

Boston Apartment | near T

10.0 out of 10, Exceptional, (2)
"Nice, clean and had everything we needed. Great locations"
Boston Apartment | near T
Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!
Fridge, microwave, oven, stovetop

Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!

2.0 star property
9.2 out of 10, Wonderful, (5)
"This home had everything we needed. Great living space. Beds are comfortable and location lends access to all parts of town. Would definately stay here again. "
Boston's historic South End! Centrally located, cozy, 2BR condo with AC, WiFi!
Lg suite for up to 8 ppl/3 floor
Terrace/patio

Lg suite for up to 8 ppl/3 floor

9.4 out of 10, Exceptional, (12)
"Property was secure and had a fantastic location.The owner was very friendly and gave so much great information about the area. Would absolutely book again!"
The price is $417
includes taxes & fees
$363 per night
May 20 - May 21
Lg suite for up to 8 ppl/3 floor
RENOVATED SUNNY 1400SF 4 BEDROOM VICTORIAN STYLE APARTMENT, STREET PARKING
Exterior

RENOVATED SUNNY 1400SF 4 BEDROOM VICTORIAN STYLE APARTMENT, STREET PARKING

9.6 out of 10, Exceptional, (141)
"The unit was completely enjoyable, the gas fireplace added a wonderful glow to all our festivities. And the street parking worked out fine."
RENOVATED SUNNY 1400SF 4 BEDROOM VICTORIAN STYLE APARTMENT, STREET PARKING
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, (469)
"The location was great. Close to the metro and good dining options. "
The price is $192
includes taxes & fees
$166 per night
May 26 - May 27
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, (191)
"Amazing stay, thank you!"
The price is $262
includes taxes & fees
$228 per night
May 5 - May 6
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 $192
includes taxes & fees
$167 per night
May 1 - May 2
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.

Frequently asked questions

How much do condos in Chestnut Hill cost?
Condos in Chestnut Hill range from $228 to $459 per night. These properties offer plenty of space for your whole family at a price that fits your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Chestnut Hill?
Chestnut Hill has 152 condos. To help you find a stay that’s right for you, take advantage of our filters to search for the perks or amenities you need.
Why book your condo in Chestnut Hill with Expedia?
Expedia makes it easy to find your dream condo in Chestnut Hill. After a luxury stay? Make use of our filters to search for properties that are 5-star rated. If you have a budget, click on how much you want to spend and then browse our amazing options. We’ll help you find the perfect place whatever your trip looks like.