Chestnut Hill Reservation Tours and Activities

Plan a trip to see Chestnut Hill Reservation

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug. 3, 2025

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
per person
Sep 6 - Sep 9
found 20 hours ago
Roundtrip flight included
Toronto (YTZ) to Boston (BOS)
9.4/10 Exceptional! (435 reviews)
Not my favorite Four Seasons. I requested that they remove any alcohol from my room and they didn’t accommodate that simple request. They seemed hurried. B-

Reviewed on Jun. 22, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug. 5, 2025

Tours & day trips

See all 251 activities
Boston Old Town Trolley Hop-on Hop-Off City Tour

Boston Old Town Trolley Hop-on Hop-Off City Tour

Activity duration is 1 day
8.8 out of 10 with 720 reviews
Free cancellation available
Price is CA $72 per adult
Boston Old Town Trolley Hop-on Hop-Off City TourOpens in new tab

Private & custom tours

See all 49 activities
North End Boston Mafia Exploration Game and Tour

North End Boston Mafia Exploration Game and Tour

Activity duration is 2 hours and 40 minutes
9.0 out of 10 with 2 reviews
Free cancellation available
The previous price was CA $16 and current price is CA $12 per adult*
North End Boston Mafia Exploration Game and TourOpens in new tab

Food, drink & nightlife

See all 38 activities
Boston to Martha's Vineyard with Optional Island Tour

Boston to Martha's Vineyard with Optional Island Tour

Activity duration is 13 hours
9.0 out of 10 with 194 reviews
Free cancellation available
Price is CA $172 per adult
Boston to Martha's Vineyard with Optional Island TourOpens in new tab

Attractions

See all 9 activities
Boston CityPASS®: Admission to Top 4 Attractions

Boston CityPASS®: Admission to Top 4 Attractions

Activity duration is 9 days
9.0 out of 10 with 140 reviews
Free cancellation available
Price is CA $109 per adult
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Adventure & outdoor

See all 7 activities
Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

Activity duration is 30 days
9.8 out of 10 with 16 reviews
Price is CA $74 per adult
Go City: Boston Explorer Pass - Choose 2 to 5 AttractionsOpens in new tab

Popular places to visit

Chestnut Hill Reservoir

Chestnut Hill Reservoir

Commune with nature and explore the great outdoors at Chestnut Hill Reservoir during your travels in Boston. Amble around this vibrant area's riverfront or attend a sporting event.

Chestnut Hill Reservoir
Boston College

Boston College

Take a campus tour or just explore the area around Boston College, a top college in Boston. Stroll along the riverfront or attend a sporting event in this vibrant area.

Boston College
Coolidge Corner Theatre

Coolidge Corner Theatre

Get tickets for a show at Coolidge Corner Theatre, a storied theater in Brookline. Experience the acclaimed theater scene and fascinating museums in this vibrant area.

Coolidge Corner Theatre

Alumni Stadium

Catch an event at Alumni Stadium during your trip to Boston. Experience the fascinating museums and acclaimed art scene in this vibrant area.

Alumni Stadium

Osher Clinical Center

Though Osher Clinical Center might be what brings you to town, perhaps you'll have a chance to explore more of Brookline while you are here.

Osher Clinical Center

Conte Forum

Catch an event at Conte Forum during your trip to Boston. Experience the area's art scene and live music.

Conte Forum

Best Lodging Options Near Chestnut Hill Reservation

AC Hotel by Marriott Boston Cleveland Circle

AC Hotel by Marriott Boston Cleveland Circle

3.5 out of 5
395 Chestnut Hill Ave, Boston, MA
AC Hotel by Marriott Boston Cleveland Circle
The Boston Hotel

The Boston Hotel

2 out of 5
40 Mt Hood Road, Boston, MA
The Boston Hotel
The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St, Brookline, MA
The Arcadian Hotel
Beacon Inn 1750

Beacon Inn 1750

3 out of 5
1750 Beacon Street, Brookline, MA
Beacon Inn 1750
"Home Away from Home" is in a Victorian home in a beautiful, safe neighborhood

"Home Away from Home" is in a Victorian home in a beautiful, safe neighborhood

Brookline
"Home Away from Home" is in a Victorian home in a beautiful, safe neighborhood
The Farrington Inn

The Farrington Inn

2 out of 5
23 Farrington Avenue, Boston, MA
The Farrington Inn
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
Hyatt Regency Boston/Cambridge
Courtyard by Marriott Boston Brookline

Courtyard by Marriott Boston Brookline

3 out of 5
40 Webster St, Coolidge Corner, Brookline, MA
Courtyard by Marriott Boston Brookline
Hampton Inn & Suites Watertown Boston

Hampton Inn & Suites Watertown Boston

2.5 out of 5
25 Bond Street, Watertown, MA
Hampton Inn & Suites Watertown Boston
See all 3,159 properties in Chestnut Hill Reservation
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.