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.

The Langham, Boston

Downtown Boston

CA $1,281

per person

Jul 30 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Boston (BOS)

9.8/10 Exceptional! (1,015 reviews)

No restaurant on site for evening meals

Reviewed on Jun 27, 2026

Boston Harbor Hotel

North End

CA $1,416

per person

Jul 31 - Aug 3

found 1 day 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 21 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 Charles Hotel

West Cambridge

CA $1,763

per person

Aug 5 - Aug 10

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.4/10 Exceptional! (1,002 reviews)

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

Reviewed on Jun 22, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

CA $4,487

per person

Aug 22 - Aug 26

found 10 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Boston (BOS)

10/10 Exceptional! (9 reviews)

thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Ready to book your vacation to Winchester?

Choose your dates

Winchester Hotel Deals

Hyatt Regency Boston/Cambridge

575 Memorial Drive Cambridge MA

Fully refundableReserve now, pay when you stay

CA $237

CA $318 total

Jul 1 - Jul 2

includes taxes & fees

9/10 Wonderful! (2,393 reviews)

"I like everything"

Reviewed on Jun 27, 2026

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $268

CA $361 total

Jul 5 - Jul 6

includes taxes & fees

9.6/10 Exceptional! (4,484 reviews)

"Clean"

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! (2,703 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.