Name: The Godfrey Hotel Boston
Price range: CA $379
Rating: 9.4

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 Atlas Hotel

Allston

CA $1,092

per person

Jul 13 - Jul 17

found 11 hours ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

9.8/10 Exceptional! (44 reviews)

Excellent staff, lovely room. Quiet, comfortable and upscale.

Reviewed on Apr 28, 2026

The Langham, Boston

Downtown Boston

CA $1,886

per person

Jun 16 - Jun 19

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

9.6/10 Exceptional! (1,005 reviews)

Private lounge offered three meals, wine, hard liquor, coffee, fruit, ice cream, etc. Well stocked & staff was superb

Reviewed on Apr 26, 2026

Hilton Boston Park Plaza

Bay Village

CA $1,186

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

8.4/10 Very Good! (3,127 reviews)

Everything was great except for the shower, which is too small.

Reviewed on Apr 29, 2026

Raffles Boston

Back Bay

CA $2,884

per person

Jun 16 - Jun 19

found 1 day ago

Roundtrip flight included

Buffalo (BUF) to Boston (BOS)

9.6/10 Exceptional! (253 reviews)

The photos doesn’t give this place justice.

Reviewed on Mar 24, 2026

By the Sea Guests Bed & Breakfast & Suites

CA $1,309

per person

Jul 15 - Jul 19

found 21 hours 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

Ready to book your vacation to Winchester?

Choose your dates

Winchester Hotel Deals

Seaport Hotel Boston

1 Seaport Lane Boston MA

Fully refundableReserve now, pay when you stay

CA $231

CA $316 total

May 3 - May 4

includes taxes & fees

9.6/10 Exceptional! (4,245 reviews)

Clean rooms and really good food.

Reviewed on Apr 29, 2026

Omni Boston Hotel at the Seaport

450 Summer Street Boston MA

Fully refundableReserve now, pay when you stay

CA $265

CA $365 total

May 1 - May 2

includes taxes & fees

9.2/10 Wonderful! (4,607 reviews)

Great hotel

Reviewed on Apr 27, 2026

The Godfrey Hotel Boston

505 Washington Street Boston MA

Fully refundableReserve now, pay when you stay

CA $379

CA $497 total

May 2 - May 3

includes taxes & fees

9.4/10 Exceptional! (5,026 reviews)

Great location! Everyone was super helpful and we enjoyed the snacks plus the water machine. Bonus points for the adjacent coffee shop & restaurant.

Reviewed on Apr 29, 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.