Glenwood Vacation Packages

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Top Holiday Package Deals in Glenwood

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

The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,544

per person

Oct 17 - Oct 20

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (262 reviews)

The Langham, Boston

Downtown Boston

CA $2,083

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (1,002 reviews)

Underwhelming. Place was clean and well maintained. But not worth additional cost above other business class hotels. Gym looks glamorous in pics and was awful. Pool small and dirty.

Reviewed on Aug 21, 2026

Iris Hotel Boston

Coolidge Corner

CA $1,885

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.4/10 Exceptional! (656 reviews)

Furnished Apartment Near Longwood

North Brookline

CA $1,697

per person

Oct 7 - Oct 12

found 23 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Boston (BOS)

6.8/10 (5 reviews)

This is more like university housing than anything else. The building is full of students and poorly maintained, with visitors following others into the entrance. Carpeting is stained, paint is chipping, blinds are broken, the a/c didn't work, the hallway smells. Communication with the Evonify owners was poor, and we had to go through Hotels.com to receive our access code/registration in time for our arrival and, ultimately, a refund. We left a few minutes after we entered the unit. Not recommended. It is not the sunny, pristine, and secure apartment that appears in the photos.

Reviewed on Jul 6, 2026

Four Seasons Hotel Boston

Bay Village

CA $2,280

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (478 reviews)

Perfect stay with our kids!

Reviewed on Aug 19, 2026

Where to stay in Glenwood

Find the best Glenwood areas and neighborhoods for the activities you enjoy most. Learn more about Glenwood

A nighttime street scene with illuminated trees, a market stall, and historic buildings.

Downtown Boston

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

A historic building with ornate architecture, a staircase, and a tree in front.

Back Bay

1 out of top 10 points of interest in this area

Victorian brownstone homes and cultural institutions like the Boston Public Library define this area. Shop at Newbury Street, Prudential Center, and Copley Place, or explore sights like Trinity Church and the John Hancock Tower.

A city skyline with modern high-rise buildings, a historic bridge, and a river with boats.

Seaport District

1 out of top 10 points of interest in this area

Experience a transformed industrial area with office towers, innovation labs, and 78 restaurants. Visit the Institute of Contemporary Art and easily access Downtown Boston via the Evelyn Moakley Bridge.

A street lamp with a lit bulb, surrounded by trees and a brick building.

Beacon Hill

1 out of top 10 points of interest in this area

Historic Federal-style rowhouses, gaslit streets, and brick sidewalks create a charming atmosphere. Explore the Boston African American National Historic Site, shop on Charles Street, and easily access MBTA stations.

A bustling riverside area with a prominent building featuring a large arched entrance, a dock with a boat, and a crowd of people.

North End

Indulge in Italian cuisine at numerous restaurants and bakeries, explore historic sites like Old North Church and Paul Revere House, and enjoy performances at NEMPAC and Improv Asylum Theater. Easily accessible via MBTA lines, buses, and ferries.

Glenwood Hotel Deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $260

CA $350 total

Sep 6 - Sep 7

includes taxes & fees

9.6/10 Exceptional! (4,828 reviews)

"Nice hotel. Room was clean and spacious. Great location near the Seaport."

Reviewed on Aug 22, 2026

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $187

CA $218 total

Aug 26 - Aug 27

includes taxes & fees

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

CA $280

CA $382 total

Aug 27 - Aug 28

includes taxes & fees

See all 4,092 properties in Glenwood

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.