Name: The Revolution Hotel
Price range: CA $88
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.

Maverick Suites at 245 Newbury St

Back Bay

CA $1,069

per person

Mar 18 - Mar 24

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

8.2/10 Very Good! (151 reviews)

Room was clean and a good size. Location was perfect - walking distance to where I needed to be.

Reviewed on Dec 2, 2025

Boston Harbor Hotel

North End

CA $1,490

per person

Apr 3 - Apr 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Charles Hotel

West Cambridge

CA $1,566

per person

Mar 12 - Mar 16

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Boston (BOS)

9.4/10 Exceptional! (1,003 reviews)

Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

Raffles Boston

Back Bay

CA $2,384

per person

Apr 23 - Apr 26

found 1 day ago

Roundtrip flight included

Halifax (YHZ) to Boston (BOS)

9.6/10 Exceptional! (181 reviews)

Everything was great — room was immaculate, hotel was very nice. Would return!

Reviewed on Feb 1, 2026

Ready to book your vacation to Winchester?

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Winchester Hotel Deals

Hilton Boston Park Plaza

50 Park Plaza Boston MA

Fully refundableReserve now, pay when you stay

CA $137

CA $216 total

Feb 22 - Feb 23

includes taxes & fees

8.2/10 Very Good! (3,113 reviews)

The hotel itself is beautiful. The lobby is grand with a vibrant bar, restaurant in the center. The staff is friendly. This was a weekend away for me and my 10 year old daughter and we wanted something luxurious. Since it was so cold outside I knew we were going to be in the room a lot. I know the ...

Reviewed on Feb 6, 2026

Harborside Inn Of Boston

185 State St Boston MA

CA $147

CA $171 total

Feb 8 - Feb 9

includes taxes & fees

9.2/10 Wonderful! (6,199 reviews)

Best price for the location! Always clean and great staff!

Reviewed on Feb 4, 2026

The Revolution Hotel

40 Berkeley Street Boston MA

Fully refundableReserve now, pay when you stay

CA $88

CA $103 total

Feb 9 - Feb 10

includes taxes & fees

9/10 Wonderful! (2,439 reviews)

Excellent customer service, beautiful room!!

Reviewed on Jan 31, 2026

See all 4,224 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.