Explore top 2026 4 Star Hotels in Winchester
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Top Winchester 4 Star hotels
Seaport Hotel Boston
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 ...
9.6/10 Exceptional! (4,804 reviews)
"Great 2 night stay in Seaport. Close to things to do nearby or grab a bite. Loved their cafe and the overall service was great, staff was accommodating and friendly. Hotel was beautiful , would absolutely stay again when in Boston area."
Reviewed on Aug 18, 2026
Hilton Boston Park Plaza
50 Park Plaza Boston MA
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $250 total per night from Sep 7 to Sep 8
$250 total
Sep 7 - Sep 8
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 ...
8.4/10 Very Good! (3,058 reviews)
"This hotel had one of the worst bathroom setups I have ever encountered. The sink had no counter space or area to place personal items—it was literally just a sink. There wasn’t even a soap dish or a box of tissues provided. The shower had no tub, door, or barrier other than a curtain, which allowed ..."
Reviewed on Aug 18, 2026
The Dagny Boston
89 Broad Street Boston MA
Fully refundableReserve now, pay when you stay
$244 nightly
The price is $284 total per night from Aug 30 to Aug 31
$284 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, ...
9.6/10 Exceptional! (7,475 reviews)
"I am so glad our family stayed here when we visited Boston. All the staff, valet were so friendly and helpful. It’s a beautiful hotel and so walkable to some great food, sites."
Reviewed on Aug 18, 2026
Omni Parker House
60 School St Boston MA
Fully refundableReserve now, pay when you stay
$324 nightly
The price is $377 total per night from Aug 30 to Aug 31
$377 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 24-hour business center, free WiFi in public ...
9/10 Wonderful! (3,673 reviews)
"This is an elegant and beautiful old hotel that has recently undergone some lovely renovations. It is in an absolutely perfect location for exploring the city, right in the heart of the freedom trail and close to subway stations. The public rooms are beautiful, and the service from all staff members, ..."
Reviewed on Aug 18, 2026
The Westin Boston Seaport District
425 Summer St Boston MA
$201 nightly
The price is $234 total per night from Sep 7 to Sep 8
$234 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 ...
Hyatt Regency Boston/Cambridge
575 Memorial Drive Cambridge MA
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $186 total per night from Sep 7 to Sep 8
$186 total
Sep 7 - Sep 8
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-in, ...
9/10 Wonderful! (2,602 reviews)
"Very good stay uber ride to town varied about $15 to $25 easier than parking in Boston. Parking fee at hotel excessive if staying there $48 or $58 overnight. Beds comfortable and clean. Came to Boston from Florida for a wedding would possible find something closer to town next time"
Reviewed on Aug 18, 2026
Harborside Inn Of Boston
185 State St Boston MA
$209 nightly
The price is $243 total per night from Aug 27 to Aug 28
$243 total
Aug 27 - Aug 28
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 ...
9.2/10 Wonderful! (6,909 reviews)
"Hotel was easy to find hard to park but the hotel provided all available options they were super friendly and cool"
Reviewed on Aug 18, 2026
citizenM Boston Back Bay
408 Newbury street Boston MA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $219 total per night from Aug 30 to Aug 31
$219 total
Aug 30 - Aug 31
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 coffee shop, a communal living room, and express check-in ...
9.4/10 Exceptional! (3,030 reviews)
"Citizen M hotels are fun, unique places. Interesting decor, up beat vibe, clean compact room design, great for our overnight stay. Very close to Fenway park, lots of nearby food choices@"
Reviewed on Aug 18, 2026
The Westin Copley Place, Boston, a Marriott Hotel
10 Huntington Ave Boston MA
Fully refundableReserve now, pay when you stay
$259 nightly
The price is $302 total per night from Aug 30 to Aug 31
$302 total
Aug 30 - Aug 31
Total with taxes and fees
This smoke-free hotel features 5 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi ...
9.2/10 Wonderful! (1,509 reviews)
"Very nice hotel. Great location. Be sure to take advantage of all benefits of the “Destination Fee” that they charge each day. We were able to get wifi access, 2 tickets to View Boston observation deck at the Prudential building, two tickets to tour Trinity Church, and a $20 per day credit at the ..."
Reviewed on Aug 18, 2026
The Royal Sonesta Boston
40 Edwin H. Land Boulevard Cambridge MA
Fully refundableReserve now, pay when you stay
$221 nightly
The price is $256 total per night from Aug 30 to Aug 31
$256 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 18 conference rooms, along with free WiFi in ...
8.8/10 Excellent! (1,911 reviews)
"Super chill. Great food/drink options. Room and bathroom spacious. AC on point (after Europe that was a God send)."
Reviewed on Aug 18, 2026
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.
4 Star Hotels Winchester
Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?
Come on, you deserve it!
The best part about staying in Winchester 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.
Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.
The best four star hotels in Winchester will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!
If you’re looking for 4 star hotels in Winchester, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.
Recent Winchester hotel reviews by fellow wanderers
The Dagny Boston
5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"I am so glad our family stayed here when we visited Boston. All the staff, valet were so friendly and helpful. It’s a beautiful hotel and so walkable to some great food, sites."
A verified traveler stayed at The Dagny Boston
