Name: The Revolution Hotel
Price range: CA $203
Rating: 9

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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.

Good Hotels Boston

South End

CA $886

per person

Jul 27 - Jul 30

found 14 hours ago

Roundtrip flight included

Québec (YQB) to Boston (BOS)

8/10 Very good! (55 reviews)

This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Boston Harbor Hotel

North End

CA $1,416

per person

Jul 31 - Aug 3

found 14 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Boston (BOS)

9.8/10 Exceptional! (1,009 reviews)

We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on Jun 15, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

CA $1,326

per person

Aug 1 - Aug 5

found 10 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (256 reviews)

Quaint, lovely place to stay

Reviewed on Jun 24, 2026

The Langham, Boston

Downtown Boston

CA $1,281

per person

Jul 30 - Aug 2

found 14 hours ago

Roundtrip non-stop flight included

Québec (YQB) to Boston (BOS)

9.8/10 Exceptional! (1,015 reviews)

Expensive 2 star hotel. Stayed here twice and 2 star is the highest I could rate it. Not value for money. Trying to be something it is not and hiking the prices up for the World Cup is shameful. Tired dated and an average hotel

Reviewed on Jun 23, 2026

The Charles Hotel

West Cambridge

CA $1,763

per person

Aug 5 - Aug 10

found 15 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.4/10 Exceptional! (1,001 reviews)

had a delicious muffin and coffee. Parking was safe and convenient.

Reviewed on Jun 22, 2026

Ready to book your vacation to Winchester?

Choose your dates

Winchester Hotel Deals

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA

CA $237

CA $318 total

Jul 1 - Jul 2

includes taxes & fees

9/10 Wonderful! (2,392 reviews)

"Loved the room layout and high ceilings. The restaurant in the hotel was excellent too."

Reviewed on Jun 27, 2026

Seaport Hotel Boston

1 Seaport Lane Boston MA

CA $268

CA $361 total

Jul 5 - Jul 6

includes taxes & fees

9.6/10 Exceptional! (4,478 reviews)

"Hotel was lovely. Room had everything in it you needed. Walking distance to Downtown Boston."

Reviewed on Jun 27, 2026

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $203

CA $237 total

Jun 30 - Jul 1

includes taxes & fees

9/10 Wonderful! (2,702 reviews)

"A beautiful place to lodge anytime anyday. I love the environment and thr general atmosphere"

Reviewed on Jun 27, 2026

See all 4,192 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.