Chestnut Hill Reservoir Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Chestnut Hill Reservoir, Boston, Massachusetts, USA

|
10.0 (2 Reviews)
1 Bedroom 4 Guests
From US $528 per night
8.0 (2 Reviews)
5 Bedrooms 11 Guests
From US $432 per night
|
10.0 (1 Review)
4 Bedrooms 8 Guests
From US $151 per night
|
10.0 (56 Reviews)
1 Bedroom 2 Guests
10.0 (10 Reviews)
2 Bedrooms 6 Guests
|
9.9 (9 Reviews)
5 Bedrooms 8 Guests
From US $146 per night
|
8.8 (147 Reviews)
1 Bedroom 2 Guests
10.0 (3 Reviews)
2 Bedrooms 4 Guests
|
9.7 (4 Reviews)
3 Bedrooms 6 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
|
9.6 (7 Reviews)
1 Bedroom 2 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
Bed & Breakfast
From US $308 per night
9.2 (92 Reviews)
8 Bedrooms 18 Guests
10.0 (1 Review)
2 Bedrooms 5 Guests
|
9.0 (10 Reviews)
2 Bedrooms 6 Guests
From US $334 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
|
9.0 (2 Reviews)
3 Bedrooms 6 Guests
From US $283 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
|
9.0 (2 Reviews)
1 Bedroom 4 Guests
10.0 (1 Review)
1 Bedroom 2 Guests
|
9.0 (1 Review)
3 Bedrooms 6 Guests
From US $264 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
|
9.0 (1 Review)
1 Bedroom 2 Guests
From US $251 per night
9.0 (1 Review)
3 Bedrooms 6 Guests
|
8.9 (36 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
2 Bedrooms 6 Guests
|
8.9 (29 Reviews)
1 Bedroom 2 Guests
10.0 (1 Review)
1 Bedroom 4 Guests
|
8.9 (7 Reviews)
1 Bedroom 2 Guests
From US $111 per night
|
8.8 (173 Reviews)
5 Bedrooms 10 Guests
9.6 (59 Reviews)
2 Bedrooms 6 Guests
From US $59 per night
|
8.8 (63 Reviews)
16 Bedrooms 26 Guests
9.6 (39 Reviews)
2 Bedrooms 6 Guests
|
8.8 (62 Reviews)
16 Bedrooms 32 Guests
9.4 (48 Reviews)
1 Bedroom 4 Guests
9.4 (22 Reviews)
1 Bedroom 4 Guests
From US $262 per night
9.4 (3 Reviews)
2 Bedrooms 4 Guests
9.0 (31 Reviews)
1 Bedroom 4 Guests
|
8.8 (19 Reviews)
1 Bedroom 2 Guests
|
8.2 (611 Reviews)
1 Bedroom 2 Guests
|
8.8 (11 Reviews)
1 Bedroom 2 Guests
From US $156 per night
7.8 (747 Reviews)
1 Bedroom 2 Guests
|
8.8 (11 Reviews)
1 Bedroom 2 Guests
From US $145 per night
|
7.4 (721 Reviews)
1 Bedroom 2 Guests
|
8.8 (10 Reviews)
1 Bedroom 4 Guests
|
8.7 (19 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 4 Guests
|
8.6 (43 Reviews)
1 Bedroom 2 Guests
|
8.6 (35 Reviews)
4 Bedrooms 8 Guests
New
1 Bedroom 4 Guests
|
8.6 (32 Reviews)
1 Bedroom 2 Guests
|
8.6 (28 Reviews)
1 Bedroom 2 Guests
|
8.6 (24 Reviews)
1 Bedroom 2 Guests
|
8.6 (15 Reviews)
1 Bedroom 2 Guests
|
8.5 (37 Reviews)
2 Bedrooms 2 Guests

About Chestnut Hill Reservoir Vacation Rentals

With more than 1122 Chestnut Hill Reservoir vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) 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 an RBO property in Chestnut Hill Reservoir.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Chestnut Hill Reservoir, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO 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 (RBOs), and other popular Airbnb-style properties in Chestnut Hill Reservoir. Places to stay near Chestnut Hill Reservoir are 574.66 ft² on average, with prices averaging US $396 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Chestnut Hill Reservoir with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Chestnut Hill Reservoir Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chestnut Hill Reservoir?

How many Rentbyowner vacation rentals are available in Chestnut Hill Reservoir?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1122 in the Chestnut Hill Reservoir area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chestnut Hill Reservoir. 

Nearby Neighborhood (12)

Neighborhood Property Count
Downtown Boston Vacation Rentals in Boston, Massachusetts 364
Back Bay Vacation Rentals in Boston, Massachusetts 291
Fenway–Kenmore Vacation Rentals in Boston, Massachusetts 213
South End Vacation Rentals in Boston, Massachusetts 177
Dorchester Vacation Rentals in Boston, Massachusetts 158
Seaport District Vacation Rentals in Boston, Massachusetts 139
Allston Vacation Rentals in Boston, Massachusetts 74
East Boston Vacation Rentals in Boston, Massachusetts 69
Beacon Hill Vacation Rentals in Boston, Massachusetts 63
North End Vacation Rentals in Boston, Massachusetts 57
Jamaica Plain Vacation Rentals in Boston, Massachusetts 49
South Boston Vacation Rentals in Boston, Massachusetts 43