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Aug 14 - Aug 16
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Top hotels in Winter Hill

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $254 total per night from Aug 30 to Aug 31
$254 total
Aug 30 - Aug 31
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
"Had a great stay! Front desk staff was attentive and helpful!"

Reviewed on Aug 13, 2026

Opens in a new windowSeaport Hotel Boston
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
$286 nightly
The price is $320 total per night from Sep 2 to Sep 3
$320 total
Sep 2 - Sep 3
Total with taxes and fees
This luxury hotel features a casino, a full-service spa, and a nightclub. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, ...
"Our favorite place to stay in Boston area! Excellent service and great food!"

Reviewed on Aug 13, 2026

Opens in a new windowEncore Boston Harbor
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
$199 nightly
The price is $232 total per night from Aug 16 to Aug 17
$232 total
Aug 16 - Aug 17
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A business center, express check-in, and express check-out are also on ...
"Small but adequate rooms. Great location. Just remember that they don’t service rooms unless you ask for it that morning!"

Reviewed on Aug 13, 2026

Opens in a new windowHarborside Inn Of Boston
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $176 total per night from Aug 16 to Aug 17
$176 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are ...
"Beautiful"

Reviewed on Aug 13, 2026

Opens in a new windowThe Revolution Hotel
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $250 total per night from Aug 23 to Aug 24
$250 total
Aug 23 - Aug 24
Total with taxes and fees
This luxury hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a 24-hour business ...
"El loby y área de restaurant se veía muy bien, buen servicio de comida, las habitaciones muy pequeñas, muy mal amuebladas, mala calidad, el servicio de valet parking muy grosero, no nos pudo ayudar porque llegamos en motocicleta, nos gritó y trató mal, la gerente en turno nos comentó que no sabían ..."

Reviewed on Aug 13, 2026

Opens in a new windowHilton Boston Park Plaza
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $220 total per night from Aug 16 to Aug 17
$220 total
Aug 16 - Aug 17
Total with taxes and fees
A gym is featured at this hotel, along with self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. There's a fireplace ...
"Very well located in South End close to shopping, restaurants and public transportation"

Reviewed on Aug 13, 2026

Opens in a new windowThe Midtown Hotel MOD Collection by Sonesta
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $315 total per night from Aug 20 to Aug 21
$315 total
Aug 20 - Aug 21
Total with taxes and fees
A full-service spa, 4 restaurants, and an outdoor pool are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like ...
Opens in a new windowOmni Boston Hotel at the Seaport
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street Boston MA
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $290 total per night from Aug 30 to Aug 31
$290 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, ...
Opens in a new windowThe Dagny Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
425 Summer St Boston MA
$210 nightly
The price is $245 total per night from Sep 7 to Sep 8
$245 total
Sep 7 - Sep 8
Total with taxes and fees
The hotel's indoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free ...
Opens in a new windowThe Westin Boston Seaport District
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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.

Winter Hill Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Winter Hill area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Winter Hill to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Winter Hill are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Winter Hill hotel reviews by fellow wanderers

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

4 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Very well located in South End close to shopping, restaurants and public transportation"
A verified traveler stayed at The Midtown Hotel MOD Collection by Sonesta
The Midtown Hotel MOD Collection by Sonesta

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