Estia Villas - Vacation Rentals in Chestnut Hill
Apartment
8.9
(
186 Reviews
)
9 Bedrooms
6 Bathrooms
20 Guests
1224.39 ft²
-
Parking -
Balcony/Terrace -
Air Conditioner -
Internet
US $405
/Night
7 Nights - $2,833
Villa
3 Bedrooms
3 Bathrooms
9 Guests
4004.17 ft²
-
Parking
-
Balcony/Terrace
-
View -
Air Conditioner
US $1,325
/Night
7 Nights - $9,275
See More Chestnut Hill Vacation Rentals
Luxury Places to Stay in Chestnut Hill
Over 749+
Luxury Places to Stay in or Near Chestnut Hill
House
10.0
(
6 Reviews
)
6 Bedrooms
8 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen -
Air Conditioner
US $3,051
/Night
7 Nights - $21,359
Apartment
16 Bedrooms
7 Bathrooms
49 Guests
5381.95 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
US $1,950
/Night
7 Nights - $13,650
New
Apartment
4 Bedrooms
4 Bathrooms
16 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $1,891
/Night
7 Nights - $13,238
Condo
15 Bedrooms
7 Bathrooms
36 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $1,649
/Night
7 Nights - $11,542
House
10.0
(
2 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
3500 ft²
-
Private Pool -
Hot Tub -
Parking
-
Pool
US $1,461
/Night
7 Nights - $10,229
House
9.4
(
82 Reviews
)
6 Bedrooms
4 Bathrooms
9 Guests
6000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $1,453
/Night
7 Nights - $10,169
Apartment
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
16 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $1,430
/Night
7 Nights - $10,009
New
House
4 Bedrooms
2 Bathrooms
16 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $1,379
/Night
7 Nights - $9,656
Find More Chestnut Hill Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chestnut Hill
Over 65+
Top-Rated Vacation Rentals with a Pool in or Near Chestnut Hill
Hostel
10.0
(
30 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $178
/Night
7 Nights - $1,247
House
10.0
(
12 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
4000 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $913
/Night
7 Nights - $6,392
Condo
9.8
(
89 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
900 ft²
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $164
/Night
7 Nights - $1,151
Hostel
9.8
(
30 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $178
/Night
7 Nights - $1,247
Bed & Breakfast
9.6
(
75 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $172
/Night
7 Nights - $1,203
House
9.6
(
29 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
2350 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $752
/Night
7 Nights - $5,266
Hostel
9.6
(
29 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $178
/Night
7 Nights - $1,247
Hotel
9.2
(
1004 Reviews
)
-
Breakfast -
Parking
-
Pool
-
Kitchen
US $356
/Night
7 Nights - $2,494
Pet-Friendly Vacation Rentals in Chestnut Hill
Over 249+
Pet-Friendly Vacation Rentals in or Near Chestnut Hill
House
10.0
(
20 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
560 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $258
/Night
7 Nights - $1,809
Apartment
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
495.14 ft²
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
US $89
/Night
7 Nights - $623
Apartment
3.6
(
4 Reviews
)
1 Bedroom
1 Bathroom
1 Guest
-
Kitchen
-
Internet
-
Pet Friendly
-
Child Friendly
US $163
/Night
7 Nights - $1,141
Apartment
10.0
(
12 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $153
/Night
7 Nights - $1,074
House
10.0
(
9 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1350 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $396
/Night
7 Nights - $2,769
New
Apartment
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $545
/Night
7 Nights - $3,812
Apartment
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $259
/Night
7 Nights - $1,813
Apartment
10.0
(
1 Review
)
3 Bedrooms
1 Bathroom
6 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $926
/Night
7 Nights - $6,481
See More Pet-Friendly Vacation Rentals in Chestnut Hill on PetFriendly.io
Large Vacation Homes & Villas in Chestnut Hill
Over 74+
Large Vacation Homes & Villas in or Near Chestnut Hill
House
10.0
(
10 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
2610 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,042
/Night
7 Nights - $7,294
Bed & Breakfast
9.4
(
109 Reviews
)
8 Bedrooms
13 Bathrooms
18 Guests
156.07 ft²
-
Balcony/Terrace
-
View
-
Air Conditioner
-
Internet
US $308
/Night
7 Nights - $2,156
Condo
10.0
(
4 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
1001 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $725
/Night
7 Nights - $5,073
Condo
10.0
(
3 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $465
/Night
7 Nights - $3,253
Condo
10.0
(
1 Review
)
10 Bedrooms
5 Bathrooms
24 Guests
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $1,007
/Night
7 Nights - $7,049
House
9.8
(
59 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2300 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $663
/Night
7 Nights - $4,643
Condo
9.4
(
13 Reviews
)
5 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $437
/Night
7 Nights - $3,058
Apartment
9.2
(
45 Reviews
)
4 Bedrooms
2 Bathrooms
12 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $637
/Night
7 Nights - $4,461
See More Family Vacation Rentals in Chestnut Hill on FVR
Wheelchair Accessible Vacation Homes in Chestnut Hill
Over 224+
Wheelchair Accessible Vacation Homes in or Near Chestnut Hill
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $479
/Night
7 Nights - $3,354
Apartment
7.8
(
46 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
301.39 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Wheelchair Accessible
US $481
/Night
7 Nights - $3,367
Hotel
9.4
(
1092 Reviews
)
-
Breakfast
-
Parking
-
Kitchen
-
Air Conditioner
US $174
/Night
7 Nights - $1,216
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $398
/Night
7 Nights - $2,784
Apartment
10.0
(
1 Review
)
2 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $262
/Night
7 Nights - $1,837
Apartment
9.6
(
4 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $441
/Night
7 Nights - $3,087
Apartment
9.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $341
/Night
7 Nights - $2,388
Apartment
8.6
(
4 Reviews
)
3 Bedrooms
1 Bathroom
4 Guests
904 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Pet Friendly
US $420
/Night
7 Nights - $2,940
Chestnut Hill Vacation Rentals and Airbnb Places to Stay Under $200
Over 232+
Chestnut Hill Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
700 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $153
/Night
7 Nights - $1,071
Apartment
9.1
(
12 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
904.17 ft²
-
Parking
-
View
-
Internet
-
Child Friendly
US $157
/Night
7 Nights - $1,099
Bed & Breakfast
10.0
(
72 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
US $151
/Night
7 Nights - $1,057
Bed & Breakfast
9.0
(
14 Reviews
)
1 Bedroom
1 Bathroom
1 Guest
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $178
/Night
7 Nights - $1,247
Apartment
9.0
(
10 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
US $181
/Night
7 Nights - $1,270
Apartment
2 Bedrooms
1 Bathroom
4 Guests
1060 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $198
/Night
7 Nights - $1,384
Apartment
2 Bedrooms
2 Bathrooms
4 Guests
1047 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $196
/Night
7 Nights - $1,374
Apartment
2 Bedrooms
1 Bathroom
4 Guests
734 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $182
/Night
7 Nights - $1,277
See More Chestnut Hill Vacation Rental Deals
Instantly Bookable Vacation Homes in Chestnut Hill
Over 370+
Instantly Bookable Vacation Homes in or Near Chestnut Hill
Apartment
10.0
(
130 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Kitchen
-
Air Conditioner
US $428
/Night
7 Nights - $2,997
Apartment
10.0
(
31 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $985
/Night
7 Nights - $6,892
Apartment
10.0
(
18 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $513
/Night
7 Nights - $3,593
Apartment
10.0
(
15 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
US $463
/Night
7 Nights - $3,243
House
10.0
(
5 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $1,352
/Night
7 Nights - $9,467
House
10.0
(
5 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $358
/Night
7 Nights - $2,507
House
10.0
(
3 Reviews
)
3 Bedrooms
3 Bathrooms
9 Guests
4200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $1,191
/Night
7 Nights - $8,335
Apartment
10.0
(
2 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $326
/Night
7 Nights - $2,285
About Chestnut Hill Vacation Rentals
With more than 2 Chestnut Hill vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chestnut Hill.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Chestnut Hill, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chestnut Hill. Places to stay near Chestnut Hill are 2614.28 ft² on average, with prices averaging US $865 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Chestnut Hill with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Chestnut Hill
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chestnut Hill.
Weather in Chestnut Hill
View the weather forecast for Chestnut Hill before booking your Chestnut Hill Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Chestnut Hill, MA
Estiavillas offers a large selection of top attractions around Chestnut Hill. Research things to do on your vacation before you visit Chestnut Hill.
Boston College
Alumni Stadium
McMullen Museum
Osher Clinical Center
Fenway Park
Boston University
Harvard University
TD Garden
Boston Common
Faneuil Hall Marketplace
Boston Convention and Exhibition Center
Gillette Stadium
New England Aquarium
Northeastern University
Boston Museum of Fine Arts
Copley Square
Harvard Square
Massachusetts General Hospital
Museum of Science
Hynes Convention Center
Other Places to Stay Near Chestnut Hill, MA
Chestnut Hill Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chestnut Hill?
There are a lot of options in Chestnut Hill. If you plan on staying in the Chestnut Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chestnut Hill:
How many vacation rentals have private pools in Chestnut Hill?
There are 9 vacation rentals with private pools near Chestnut Hill. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chestnut Hill are best for families?
If you are looking for a family-friendly vacation home in Chestnut Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestnut Hill:
How many vacation rentals are available in Chestnut Hill?
Currently, the total number of properties listed in 2026 is over 2 in the Chestnut Hill area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chestnut Hill.
