Name: citizenM Boston North Station
Price range: CA $253
Rating: 9.2

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.

Boston Lodge and Suites

Dorchester

CA $705

per person

Nov 21 - Nov 25

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

8.4/10 Very Good! (186 reviews)

Raffles Boston

Back Bay

CA $2,394

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

9.6/10 Exceptional! (154 reviews)

I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.

Reviewed on Aug. 28, 2025

Boston Harbor Hotel

North End

CA $3,006

per person

Oct 12 - Oct 17

found 16 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Boston (BOS)

9.8/10 Exceptional! (1,013 reviews)

Favorite place to stay

Reviewed on Aug. 28, 2025

Studio Allston Hotel

Brighton

CA $1,539

per person

Oct 13 - Oct 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Boston (BOS)

8.6/10 Excellent! (1,098 reviews)

Simple but very nice.

Reviewed on Aug. 29, 2025

Sesuit Harbor House

CA $911

per person

Oct 23 - Oct 27

found 15 hours ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.6/10 Exceptional! (168 reviews)

We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!

Reviewed on Aug. 25, 2025

Ready to book your vacation to Winchester?

Choose your dates

Winchester Hotel Deals

Seaport Hotel Boston

1 Seaport Lane, Boston, MA

CA $211

CA $253 total

Sep 1 - Sep 2

includes taxes & fees

Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Fully refundableReserve now, pay when you stay

CA $267

CA $366 total

Sep 1 - Sep 2

includes taxes & fees

citizenM Boston North Station

80-120 Causeway Street, Boston, MA

Fully refundableReserve now, pay when you stay

CA $253

CA $294 total

Sep 1 - Sep 2

includes taxes & fees

9.2/10 Wonderful! (3,709 reviews)

"So modern, clean and comfortable"

Reviewed on Aug. 27, 2025

See all 3,766 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.