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Top hotels and accommodation in Winchester

Exterior
Omni Boston Hotel at the Seaport
4.5 star property
9.0 out of 10, Wonderful, (2047)
"The staff was friendly. Our room was super clean, comfy, and had a great view of the city. I loved the floor to ceiling windows. "
The price is NZ$380
per night
9 Jun - 10 Jun
Omni Boston Hotel at the Seaport
Interior
The Arcadian powered by Sonder
3.5 star property
8.0 out of 10, Very good, (2144)
"Great place and venue"
The price is NZ$363
per night
27 May - 28 May
The Arcadian powered by Sonder
Interior
citizenM Boston North Station
4.0 star property
9.2 out of 10, Wonderful, (2282)
"What a cool property! I’m looking forward to coming back to stay again soon."
The price is NZ$378
per night
27 May - 28 May
citizenM Boston North Station
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Exterior
YOTEL Boston
4.0 star property
8.4 out of 10, Very good, (1669)
"Room was clean and well appointed. Staff was courteous. Fine for our short stay (1 night) but room was extremely small. "
The price is NZ$357
per night
16 Jun - 17 Jun
YOTEL Boston
Front of property
Harborside Inn Of Boston
4.0 star property
9.2 out of 10, Wonderful, (3510)
"The only thing we didn’t like was that we had to pay extra for a room with a window, and then the window was just inside the building. Wish I had know that I wouldn’t have paid extra for it. "
The price is NZ$530
per night
27 May - 28 May
Harborside Inn Of Boston
Apartment, 2 Bedrooms
Encore Boston Harbor
5.0 star property
9.6 out of 10, Exceptional, (2215)
"Fabulous"
The price is NZ$532
per night
23 May - 24 May
Encore Boston Harbor
Restaurant
The Westin Boston Seaport District
4.0 star property
8.8 out of 10, Excellent, (1433)
"The Westin Seaport District is in the perfect area for walking to restaurants, bars, the T, the Bay! You can catch a trolley tour practically in front of the hotel! The staff was friendly, helpful, and professional. Definitely enjoyed my stay here."
The price is NZ$378
per night
26 May - 27 May
The Westin Boston Seaport District
Exterior
The Bostonian Boston
4.0 star property
8.4 out of 10, Very good, (2120)
"10/10 I was super hesitant bc the reviews are mixed but the location is amazing. The room was super spacious. Everything was walking distance -> north end was a 5 min walk. "
The price is NZ$413
per night
27 May - 28 May
The Bostonian Boston
Indoor pool, pool loungers
Sheraton Boston, a Marriott Hotel
4.0 star property
8.4 out of 10, Very good, (1542)
"The property was clean and convenient. I will stay again. "
The price is NZ$418
per night
24 May - 25 May
Sheraton Boston, a Marriott Hotel
Water view
Battery Wharf Hotel, Boston Waterfront
4.5 star property
8.6 out of 10, Excellent, (1478)
"Pleasant place. Housekeeping was excellent and flexible. Lovely location. "
The price is NZ$435
per night
16 Jun - 17 Jun
Battery Wharf Hotel, Boston Waterfront
Exterior
Copley House
3.0 star property
8.6 out of 10, Excellent, (1213)
"It's in a great atea, but the stairs ate an adventure."
The price is NZ$460
per night
23 May - 24 May
Copley House
Meeting facility
Aloft Boston Seaport District
3.0 star property
8.8 out of 10, Excellent, (1004)
"Clean and quiet. Perfect quick stay for a family trip. Staff was very nice"
The price is NZ$319
per night
27 May - 28 May
Aloft Boston Seaport District
Deluxe Room, 1 King Bed (Panorama) | View from room
The Royal Sonesta Boston
4.0 star property
8.2 out of 10, Very good, (1129)
"Stayed here multiple times. Just love the hotel and the surrounding area. Recommend rooms with the river view."
The price is NZ$376
per night
2 Jun - 3 Jun
The Royal Sonesta Boston
Lounge
HI Boston - Hostel
2.0 star property
8.6 out of 10, Excellent, (1000)
"Amazing staff, they speak clearly and communicate well. Fun time getting to know others. Close to real good food and shops. Would visit again "
The price is NZ$375
per night
16 Jun - 17 Jun
HI Boston - Hostel
Reception
Hampton Inn & Suites Boston Crosstown Center
3.0 star property
7.8 out of 10, Good, (1001)
"The staff were very friendly and informative. The shuttle was convenient and breakfast was great! Somewhat disappointed in the pool, it water was cold and it was playing the same add over and over again on the speakers."
The price is NZ$289
per night
27 May - 28 May
Hampton Inn & Suites Boston Crosstown Center
Executive Suite, 1 King Bed
Element Boston Seaport District
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Great for kids, pool was perfect temperature, staff was very friendly and helpful. Breakfast was actually very very tasty and satisfied all of us (no easy feat!). Would recommend and stay again!"
The price is NZ$343
per night
27 May - 28 May
Element Boston Seaport District
Exterior
Hilton Garden Inn Boston Logan Airport
3.0 star property
9.2 out of 10, Wonderful, (1652)
"Very clean property. Staff friendly. Only negative was having to call twice for pickup. They said traffic but 40 minutes is too long when ride to hotel was less than 10 minutes "
The price is NZ$326
per night
28 May - 29 May
Hilton Garden Inn Boston Logan Airport
Reception
Quality Inn Boston - Revere
2.5 star property
7.4 out of 10, Good, (1000)
"Convenient location "
Quality Inn Boston - Revere
Terrace/patio
Homewood Suites by Hilton Boston Seaport District
3.0 star property
9.0 out of 10, Wonderful, (549)
"Just what we needed....quiet rooms, excellent bed and walking distance to the cruise terminal "
The price is NZ$313
per night
27 May - 28 May
Homewood Suites by Hilton Boston Seaport District
Exterior
Ramada by Wyndham Boston
2.5 star property
6.8 out of 10, (1006)
"I loved the stay and the breakfast I had a great time as well!"
The price is NZ$259
per night
2 Jun - 3 Jun
Ramada by Wyndham Boston
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See all available 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.

More cheap accommodation in Winchester

Motel 6 Framingham, MA - Boston West

Motel 6 Framingham, MA - Boston West

1668 Worcester Rd, Framingham, MA
The price is NZ$149 per night from May 20 to May 21
NZ$149
per night
20 May - 21 May
7/10 Good! (1,002 reviews)

Stay near top Winchester attractions

Image for Fenway Park

Fenway Park

4.5/5(9 reviews)

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

See properties
Fenway Park

Winchester hotels information

Number of reviews
6,593
Accommodation
3,263 hotels
Lowest Price
NZ$149
Highest Price
NZ$532

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 The Dagny Boston and Four Points by Sheraton Boston Newton. See all available top hotels, or vacation rentals in Winchester.

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

Beautiful, Cozy Ultra Convenient Salem Home: This holiday home rental outside of Winchester is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 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. TD Garden, Fenway Park and New England Aquarium 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?

The picturesque setting of Middlesex Fells Reservation and Winter Pond exemplify the area's natural beauty. Additionally, you'll find TD Garden and Fenway Park 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, April and March, with each month seeing an average of 15 cm of snowfall.

Recent Reviews in Winchester
Expedia verified reviews

Copley Square Hotel

Copley Square Hotel

5/5 Excellent
"Close to public transit and plenty nearby in walking distance "
A verified traveller stayed at Copley Square Hotel
Posted 8 hours ago
Copley Square Hotel