Name: The Revolution Hotel
Price range: CA $307
Rating: 9

Your Winchester Vacation

Book a Winchester vacation package that includes everything you need and nothing you don't. Great for nightlife, shopping and bars and pubs, consider staying in the neighborhood of Downtown Boston. A trip to Winchester is a terrific opportunity to see the sights. Be sure to look around renowned attractions like Harvard Square, Harvard University and Bentley College. Stop dreaming and start traveling. Browse the broad range of options on Expedia today and finally put your Winchester vacation plans into gear!

Top Winchester Vacation Deals

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

Hotel Ivy Boston Common

Bay Village

CA $960

per person

Jul 3 - Jul 6

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

8.4/10 Very Good! (1,430 reviews)

The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.

Reviewed on May 8, 2026

By the Sea Guests Bed & Breakfast & Suites

CA $963

per person

Jul 20 - Jul 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.2/10 Wonderful! (185 reviews)

Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Nantucket Inn

CA $1,925

per person

Jul 27 - Jul 31

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9/10 Wonderful! (670 reviews)

Room was clean upon arrival, but there was no "service" daily .... No bed making, no clean towels, no kleenex, etc. We've stayed at Nantucket Inn several time and always like it. We were very disappointed with the daily service this time.

Reviewed on May 8, 2026

Chatham Tides

CA $2,018

per person

Jul 20 - Jul 24

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.4/10 Exceptional! (687 reviews)

Will go back very quaint and relaxing

Reviewed on May 8, 2026

The Ritz-Carlton, Boston

Downtown Boston

CA $3,563

per person

Jun 16 - Jun 21

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Boston (BOS)

9/10 Wonderful! (453 reviews)

Top notch. Every member of the staff was a credit to his or her profession.

Reviewed on May 3, 2026

Ready to book your vacation to Winchester?

Choose your dates

Winchester Hotel Deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

CA $317

per night

May 25 - May 26

9.6/10 Exceptional! (4,304 reviews)

The breakfast very good

Reviewed on May 9, 2026

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

CA $283

per night

May 25 - May 26

9.2/10 Wonderful! (4,646 reviews)

We were at an event that was for over 900 people, the food came out hot and delicious. The wait staff were extremely friendly and helpful. The entire event was flawless.

Reviewed on May 9, 2026

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $307

per night

May 21 - May 22

9/10 Wonderful! (2,607 reviews)

A perfect location in the Back Bay area!

Reviewed on May 9, 2026

See all 4,170 properties in Winchester

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.