Name: The Dagny Boston
Price range: $330 total
Rating: 9.4

Your Winter Hill Vacation

Take the fuss out of organizing your next escape by booking a Winter Hill vacation package. Immerse yourself in the sounds and sights of this wonderful neighborhood and experience what it has to offer. When it's time to take in the sights, you'll find lots of popular attractions nearby including Assembly Row, LEGOLAND® Discovery Center and Somerville Theatre. Visit one, two or all during your trip to Winter Hill. No matter your travel plans or budget, booking your dream Winter Hill vacation is simple with Expedia.

The Latest Winter Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.

The Revolution Hotel

South End

Save 100% on your flight

$184

per person

Dec 6 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9/10 Wonderful! (2,149 reviews)

No parking. The room had a smell like it was painted gave me a headache but nice and cute little hotel. The staff was so nice!!!!

Reviewed on Oct 14, 2025

Boston Lodge and Suites

Dorchester

$302

per person

Dec 6 - Dec 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

8.4/10 Very Good! (186 reviews)

Raffles Boston

Back Bay

$806

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (160 reviews)

I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.

Reviewed on Oct 7, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

Save 100% on your flight

$771

per person

Dec 18 - Dec 22

found 3 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.6/10 Exceptional! (244 reviews)

I was hoping it would be a very nice place from the pictures I saw online. I was not at all disappointed, everything was wonderful, the room was so beautiful, very clean and the linens were so comfy. The area around the Inn is lovely, very walkable, with plenty of shopping and restaurants.

Reviewed on Aug 12, 2025

Beacon Hill Hotel

Beacon Hill

Save 100% on your flight

$1,059

per person

Dec 7 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

9/10 Wonderful! (246 reviews)

Lean room, nice staff but the elevator broke and it took a while to fix it

Reviewed on Oct 1, 2025

Where to stay in Winter Hill

Find the best Winter Hill areas and neighborhoods for the activities you enjoy most. Learn more about Winter Hill

Downtown Boston

4.5/5(2,415 area reviews)

Densely packed with highrise buildings, this area boasts landmarks like Custom House Tower and is close to Quincy Market, Faneuil Hall, and the Old State House. Find headquarters of major banks, hotels, and investment firms here.

Winter Hill Hotel Deals

The Revolution Hotel

40 Berkeley Street, Boston, MA

Fully refundableReserve now, pay when you stay

$129 nightly

$150 total

Nov 9 - Nov 10

Total with taxes and fees

8.8/10 Excellent! (2,159 reviews)

"The staff were incredibly helpful! Accommodation, although slightly unuasal, not having a en-suite bathroom in the room, it was easy, safe, convenient having it down the hall. This arrangement made the cost about half of a compreable room elsewhere and the condition and decor of the rooms and hotel ..."

Reviewed on Oct 9, 2025

citizenM Boston North Station

70 Causeway Street, Boston, MA

Fully refundableReserve now, pay when you stay

$219 nightly

$255 total

Nov 9 - Nov 10

Total with taxes and fees

9.2/10 Wonderful! (3,907 reviews)

"."

Reviewed on Oct 11, 2025

The Dagny Boston

89 Broad Street, Boston, MA

Fully refundableReserve now, pay when you stay

$284 nightly

$330 total

Oct 31 - Nov 1

Total with taxes and fees

9.4/10 Exceptional! (6,593 reviews)

"Clean, nice hotel in a great area. Would definitely recommend."

Reviewed on Oct 13, 2025

See all 3,747 properties in Winter Hill

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.