Pleasure Point Tours

Visit Pleasure Point

Activities

Holliston Travel Guide

Plan a trip to see Pleasure Point

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

Wayfinder Newport

Save 100% on your flight

$709

per person

May 28 - Jun 2

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Providence (PVD)

8/10 Very Good! (1,007 reviews)

Hotel was great and smelled so good!

Reviewed on Mar 13, 2026

The Langham, Boston

Downtown Boston

Save 100% on your flight

$1,099

per person

Jun 7 - Jun 10

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

9.6/10 Exceptional! (1,004 reviews)

Great location within walking distance to many of Boston’s best spots including Faneuil Market, North End “little Italy,” and more! The hotel staff were welcoming and kind during our visit, and our room was well kept. No complaints.

Reviewed on Mar 14, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$1,163

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Boston (BOS)

9.8/10 Exceptional! (1,001 reviews)

Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!

Reviewed on Mar 14, 2026

Popular places to visit

Framingham City Hall

5/5(1 review)

Framingham City Hall is just one of the places to see in Framingham, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the lively bars while you're in the area.

Stoddard Park

Why not spend a lazy afternoon at Stoddard Park during your trip to Holliston? Wander the lakeside and beaches while you're in the area.

Pinecrest Golf Club

Enjoy a round of golf in Holliston at Pinecrest Golf Club. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Rocky Narrows

Enjoy an outing to Rocky Narrows during your stay in Sherborn. Stroll along the riverfront or seek out the jogging trails.

Bridge Island Meadows

Commune with nature and explore the great outdoors at Bridge Island Meadows during your travels in Millis. Experience the area's great live music or attend a sporting event.

Ashland State Park

3.5/5(2 reviews)

You can take time to visit Ashland State Park during your travels to Ashland. While you're in the area, wander around the parks.

Best Lodging Options Near Pleasure Point

Check availability on hotels close to Pleasure Point

Sheraton Boston Needham Hotel

100 Cabot St Needham MA

Embassy Suites by Hilton Boston Marlborough

123 Boston Post Rd W Marlborough MA

Boston Marriott Newton

2345 Commonwealth Avenue Newton MA

Four Points by Sheraton Boston Newton

320 Washington Street Newton MA

Hampton Inn & Suites Boston/Waltham

135 2nd Ave Waltham MA

Hampton Inn & Suites Watertown Boston

25 Bond Street Watertown MA

Arcadian Hotel

1200 Beacon St Brookline MA

Courtyard by Marriott Boston-Cambridge

777 Memorial Dr Cambridge MA

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA

See all 4,761 properties in Pleasure Point

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.