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Top hotels and accommodation in Winchester

The Revolution Hotel

3.5 star property
8.8 out of 10, Excellent, (1861)
"The hotel was great- all staff were really nice and accommodating! Beds were incredibly comfy. We had a room with a shared bathroom. It was always clean and we never had to wait to use it. Will definitely be back! "
The price is AU$158
includes taxes & fees
5 Jan - 6 Jan
The Revolution Hotel

The Dagny Boston

4.0 star property
9.4 out of 10, Exceptional, (5191)
"Great room staff is smiling and helpful "
The price is AU$345
includes taxes & fees
5 Jan - 6 Jan
The Dagny Boston

The Godfrey Hotel Boston

4.0 star property
9.4 out of 10, Exceptional, (3662)
"Great all around"
The Godfrey Hotel Boston

Harborside Inn Of Boston

4.0 star property
9.2 out of 10, Wonderful, (4512)
"The hotel is great. Clean. Friendly. Incredible location. Great value. Only real issue is the "Cabin" rooms are in the basement and have no windows. Yes, after i checked in i re-reviewed my booking and it does say "No Windows" but i feel it ahould be pointed out better somehow. Again, not sure how they could point it out better. It wasnt a big deal for us, but could be for others. I'll stay here next time in Boston, but opt for a room with windows. "
The price is AU$205
includes taxes & fees
5 Jan - 6 Jan
Harborside Inn Of Boston

Hilton Boston Park Plaza

4.0 star property
8.4 out of 10, Very good, (3293)
"Only disappointed for our stay was the size of the room. It was so small. The shower snd toilet facility one of the smallest i have been to. If we were large people, we would have struggled both using shower and toilet. Apart from that, the hotel and all that it offers is fantastic. We only stayed 1 night so was able to cope with room size. Apart from that, the hotel and a"
The price is AU$275
includes taxes & fees
19 Jan - 20 Jan
Hilton Boston Park Plaza

citizenM Boston Back Bay

4.0 star property
9.2 out of 10, Wonderful, (522)
"Hannah the women who checked me in was fantastic, friendly and helpful. Top notch."
The price is AU$223
includes taxes & fees
5 Jan - 6 Jan
citizenM Boston Back Bay

citizenM Boston North Station

4.0 star property
9.2 out of 10, Wonderful, (2910)
"Please add a review "
The price is AU$223
includes taxes & fees
5 Jan - 6 Jan
citizenM Boston North Station

Omni Boston Hotel at the Seaport

4.0 star property
9.2 out of 10, Wonderful, (3081)
"Clean and comfortable. Beautiful view from our room. Friendly and efficient staff"
The price is AU$340
includes taxes & fees
18 Jan - 19 Jan
Omni Boston Hotel at the Seaport

Omni Parker House

4.0 star property
8.8 out of 10, Excellent, (2916)
"Great historic hotel in the heart of Boston."
The price is AU$350
includes taxes & fees
10 Jan - 11 Jan
Omni Parker House

Encore Boston Harbor

5.0 star property
9.6 out of 10, Exceptional, (2608)
"Fantastic "
The price is AU$456
includes taxes & fees
2 Feb - 3 Feb
Encore Boston Harbor

Seaport Hotel Boston

4.0 star property
9.6 out of 10, Exceptional, (2667)
"Everything was great"
The price is AU$311
includes taxes & fees
4 Jan - 5 Jan
Seaport Hotel Boston

Hampton Inn Boston Seaport District

3.0 star property
9.2 out of 10, Wonderful, (2035)
"Very nice "
The price is AU$252
includes taxes & fees
9 Jan - 10 Jan
Hampton Inn Boston Seaport District

Copley Square Hotel, a FOUND Hotel

4.0 star property
8.6 out of 10, Excellent, (3207)
"Great staff "
The price is AU$186
includes taxes & fees
20 Jan - 21 Jan
Copley Square Hotel, a FOUND Hotel

Club Quarters Hotel Faneuil Hall, Boston

4.0 star property
8.8 out of 10, Excellent, (2451)
"It was ok"
The price is AU$242
includes taxes & fees
5 Jan - 6 Jan
Club Quarters Hotel Faneuil Hall, Boston

The Arcadian powered by Sonder

3.5 star property
8.0 out of 10, Very good, (2853)
"The staff at The Arcadian were exceptionally welcoming and friendly, making for a pleasant stay. The hotel offers free all-day breakfast, which is a fantastic perk, and the gym is well-equipped with dumbbells, a few machines, and treadmills. The room was clean, comfortable, and thoughtfully maintained. The location is another highlight—it’s in a walkable area and just a short distance from Fenway Park, making it an ideal choice for catching a Red Sox game. Plus, the T (Boston subway line) is...
The price is AU$253
includes taxes & fees
24 Jan - 25 Jan
The Arcadian powered by Sonder

Hyatt Regency Boston

4.0 star property
8.8 out of 10, Excellent, (1302)
"Awesome property "
The price is AU$325
includes taxes & fees
17 Jan - 18 Jan
Hyatt Regency Boston

YOTEL Boston

4.0 star property
8.4 out of 10, Very good, (1855)
"Not bad overall. Small rooms and no wash cloths in the bathroom. Friendly people and beautiful rooftop view with bar and food. "
The price is AU$261
includes taxes & fees
16 Jan - 17 Jan
YOTEL Boston

The Westin Boston Seaport District

4.0 star property
9.0 out of 10, Wonderful, (1730)
"My family and I spent New Year's Eve as guests. We were upgraded to city view. This allowed us to see the fireworks! The kids loved the pool and the parents loved the Starbucks in the lobby. Would absolutely recommend! "
The price is AU$336
includes taxes & fees
5 Jan - 6 Jan
The Westin Boston Seaport District

Hyatt Place Boston/Seaport District

3.0 star property
9.4 out of 10, Exceptional, (1855)
"The room was nice and had a good view of the harbor, which we enjoyed. Staff was friendly and helpful."
The price is AU$269
includes taxes & fees
5 Jan - 6 Jan
Hyatt Place Boston/Seaport District

Aloft by Marriott, Boston Seaport District

3.0 star property
9.0 out of 10, Wonderful, (1143)
"Very nice, perfect for our one night stay! "
The price is AU$231
includes taxes & fees
6 Jan - 7 Jan
Aloft by Marriott, Boston Seaport District
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.
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Frequently asked questions

What's the best place to stay in Winchester?

Located 8.7 mi (14 km) from the heart of Winchester, Omni Boston Hotel at the Seaport is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Hilton Boston Park Plaza and The Dagny Boston. See all available top hotels, or vacation rentals in Winchester.

What are some of the best holiday rentals that Winchester has to offer?

Centrally located in the heart of Boston near T: This holiday home rental outside of Winchester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Winchester.

If I need to cancel my hotel reservation in Winchester, will I receive a refund?

Yes, most hotel bookings are fully refundable if cancelled before the hotel’s cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

What are some accommodation options with pools in Winchester?

Embassy Suites Boston Logan Airport: 3.5-star hotel located near New England Aquarium. Features a snack bar, an indoor pool and free buffet breakfast. Seaport Hotel Boston and Hilton Boston Logan Airport are two additional hotels with an on-site pool. View all hotels with pools in Winchester.

What is staying in Winchester like?

Visitors can enjoy all that Winchester has to offer, including the football matches and lake views. Boston Common, TD Garden and Fenway Park are some of the top sights around the area. In Winchester, there are 2 hotels and other accommodation options to choose from. Find out more about Winchester.

What should I do while I'm visiting Winchester?

A couple of favourite places to visit are Winter Pond and Middlesex Fells Reservation. Additionally, you'll find Boston Common and TD Garden in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.

How can I get around Winchester?

To venture out into the surrounding area, ride one of the trains from Winchester Station or Winchester Wedgemere Station. If you want to venture out around the area, you may want a rental car in Winchester for your journey.

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.