Find Vacation Rentals in Chestnut Hill

We have 492 properties to choose from
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Popular Chestnut Hill Vacation Rentals

Find the perfect Chestnut Hill vacation rental

House Chestnut Hill
from $80 per night
2 guests ∙ 2 bedrooms

House

Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
House Chestnut Hill
from $220 per night
3 guests ∙ 2 bedrooms

House

4.6
Excellent(25 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
House Chestnut Hill
from $1,012 per night
House ∙ 16 guests ∙ 6 bedrooms

557 m² House

4.7
Excellent(88 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
House Chestnut Hill
from $249 per night
6 guests ∙ 3 bedrooms

House

4.8
Outstanding(81 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
Apartment Chestnut Hill
from $191 per night
2 guests ∙ 1 bedroom

Apartment

4.5
Excellent(42 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
Condo Chestnut Hill
from $161 per night
Condo ∙ 4 guests ∙ 2 bedrooms

84 m² Condo

4.9
Outstanding(97 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
Aparthotel Chestnut Hill
from $359 per night
Aparthotel ∙ 5 guests ∙ 2 bedrooms

112 m² Aparthotel

5.0
Outstanding(98 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
House Chestnut Hill
from $242 per night
6 guests ∙ 2 bedrooms

House

5.0
Outstanding(2 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Vrbo
Details
Apartment Chestnut Hill
from $321 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

75 m² Apartment

5.0
Outstanding
Chestnut Hill, Newton, Massachusetts, United States
Agoda
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Recommended Rentals With Pools

Apartment  Chestnut Hill
from $269 per night
Apartment ∙ 4 guests ∙ 1 bedroom

65 m² Apartment

4.0
Very good(14 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Pool
Vrbo
Details
House  Chestnut Hill
from $607 per night
House ∙ 8 guests ∙ 4 bedrooms

372 m² House

5.0
Outstanding(8 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Pool
Vrbo
Details
Apartment  Chestnut Hill
from $154 per night
Apartment ∙ 4 guests ∙ 1 bedroom

56 m² Apartment

Chestnut Hill, Newton, Massachusetts, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Chestnut Hill
from $298 per night
House ∙ 2 guests ∙ 1 bedroom

30 m² House

4.5
Excellent(7 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Pet-friendly
Vrbo
Details
Condo  Chestnut Hill
from $178 per night
5 guests ∙ 2 bedrooms

Condo

Chestnut Hill, Newton, Massachusetts, United States
Pet-friendly
Vrbo
Details
Apartment  Chestnut Hill
from $144 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

56 m² Apartment

Chestnut Hill, Newton, Massachusetts, United States
Pet-friendly
Vrbo
Details
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Vacation rentals with a balcony

Apartment  Chestnut Hill
from $334 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

94 m² Apartment

Chestnut Hill, Newton, Massachusetts, United States
Balcony
Vrbo
Details
Apartment  Chestnut Hill
from $243 per night
Apartment ∙ 2 guests ∙ 1 bedroom

67 m² Apartment

Chestnut Hill, Newton, Massachusetts, United States
Balcony
Vrbo
Details
Bed and breakfast  Chestnut Hill
from $72 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

The Pistachio Room (Room 2) at The Perthshire House.

4.8
Outstanding(64 ratings)
Chestnut Hill, Newton, Massachusetts, United States
Balcony
Vrbo
Details
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Frequently Asked Questions

What is the average price per night for accommodation in Chestnut Hill?

Prices for a stay in Chestnut Hill begin at $71 per night.

Are there any vacation rentals available to book in Chestnut Hill?

You can find 492 available vacation rentals in Chestnut Hill.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Chestnut Hill

Looking for a vacation rental in Chestnut Hill? Tripping.com has 96 vacation rental homes available in Chestnut Hill. You'll find 0 studios, 46 1-bedroom, 16 2-bedroom and 34 rentals with 3 or more bedrooms ranging from $51 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Chestnut Hill is $344 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Chestnut Hill home is $25. Wondering if you can bring your dog or cat along with you? There are 4 pet-friendly vacation rentals available in Chestnut Hill. In addition to accommodating pets, Chestnut Hill rentals offer a variety of amenities. In particular, 93 rentals have Internet and WiFi, 83 have TV and/or cable and 12 have a pool or hot tub. Search properties from 5 vacation rental sites in Chestnut Hill where the top providers in that area are HomeAway, Expedia, and Booking.com. There are 45 HomeAway rentals, 24 Expedia short term rentals and 17 Booking.com vacation rentals.

Popular Day Trips Near Chestnut Hill

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