Best Resorts in Winchester

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Check prices for these dates

Next weekend
Jun 12 - Jun 14
In two weeks
Jun 19 - Jun 21
In one month
Jul 3 - Jul 5
In two months
Jul 31 - Aug 2
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Bar (on property)

citizenM Boston Back Bay

citizenM Boston Back Bay
4.0 star property
Fenway–Kenmore
9.4 out of 10, Exceptional, (2,732 reviews)
"Great location, walked to Fenway Park and Newbury St. would stay again for location alone."
United States
Hettie
$197 nightly
The price is $229
Jul 5 - Jul 6
Total with taxes and fees
citizenM Boston Back Bay
Exterior

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (4,410 reviews)
"Great place to stay!!"
United States
Rickey
$219 nightly
The price is $254
Jul 5 - Jul 6
Total with taxes and fees
Seaport Hotel Boston
View from property

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta
3.0 star property
Back Bay
8.2 out of 10, Very Good, (425 reviews)
"Excellent location for a short visit to Boston."
United States
Carlos
$225 nightly
The price is $262
Jul 2 - Jul 3
Total with taxes and fees
The Midtown Hotel MOD Collection by Sonesta
Executive Double Room | Individually decorated, individually furnished, blackout drapes

The Northshore Hotel - Boston/Danvers

The Northshore Hotel - Boston/Danvers
2.0 star property
Danvers
7.6 out of 10, Good, (1,006 reviews)
"Great place to stay. It is a Motel and not a Hotel. Beautifully updated. Great breakfast. Wonderful people."
United States
Mary
$119 nightly
The price is $133
Jun 7 - Jun 8
Total with taxes and fees
The Northshore Hotel - Boston/Danvers
Bar (on property)

Hyatt Place Boston/Seaport District

Hyatt Place Boston/Seaport District
3.0 star property
Seaport District
9.4 out of 10, Exceptional, (2,385 reviews)
"Amazing place to stay!"
United States
Heather
$235 nightly
The price is $274
Jun 7 - Jun 8
Total with taxes and fees
Hyatt Place Boston/Seaport District
Exterior

Hampton by Hilton at the Boston Seaport District

Hampton by Hilton at the Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,874 reviews)
"Great for just an overnight.. clean room and friendly staff."
United States
Barbara
$154 nightly
The price is $180
Jul 5 - Jul 6
Total with taxes and fees
Hampton by Hilton at the Boston Seaport District
Presidential Suite | Premium bedding, down comforters, in-room safe, blackout drapes

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.2 out of 10, Wonderful, (2,052 reviews)
"Awesome stay; amazing staff and great service"
United States
Manjit
$212 nightly
The price is $247
Jul 5 - Jul 6
Total with taxes and fees
Hyatt Regency Boston
Restaurant

Sonesta Select Boston Danvers

Sonesta Select Boston Danvers
3.0 star property
Danvers
8.6 out of 10, Excellent, (1,007 reviews)
"Great stay"
United States
Verinda
$167 nightly
The price is $186
Jun 30 - Jul 1
Total with taxes and fees
Sonesta Select Boston Danvers
View from property

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,010 reviews)
"Very cute, great vacation spot"
United States
sharon
$178 nightly
The price is $199
Jun 7 - Jun 8
Total with taxes and fees
Nantasket Beach Resort
Front of property

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront
4.5 star property
North End
8.8 out of 10, Excellent, (1,849 reviews)
"Great view and friendly staff"
United States
Bryan
$216 nightly
The price is $228
Jun 7 - Jun 8
Total with taxes and fees
Battery Wharf Hotel, Boston Waterfront
Front of property

Harborside Inn Of Boston

Harborside Inn Of Boston
4.0 star property
Downtown Boston
9.2 out of 10, Wonderful, (6,624 reviews)
"Location was excellent, room was nice. Would stay there again"
United States
Anthony
$169 nightly
The price is $197
Jun 7 - Jun 8
Total with taxes and fees
Harborside Inn Of Boston
Rooftop terrace

YOTEL Boston

YOTEL Boston
4.0 star property
Seaport District
8.8 out of 10, Excellent, (2,531 reviews)
"Very cool hotel and location!"
United States
Emily
$229 nightly
The price is $267
Jul 5 - Jul 6
Total with taxes and fees
YOTEL Boston
4 restaurants; breakfast, lunch, and dinner served

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4,687 reviews)
"Great stay."
United States
Cassendra
$250 nightly
The price is $291
Jun 6 - Jun 7
Total with taxes and fees
Omni Boston Hotel at the Seaport
Beach

The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College
3.5 star property
Beverly
9.2 out of 10, Wonderful, (1,171 reviews)
"Top notch place to stay, and the ability to walk to the shore was delightful."
United States
Dirk
$160 nightly
The price is $179
Jun 15 - Jun 16
Total with taxes and fees
The Wylie Inn and Conference Center at Endicott College
Interior

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End
3.0 star property
South End
9.0 out of 10, Wonderful, (1,005 reviews)
"Great location, close to lots of restaurants and shopping. Bar and restaurant were good and convenient. "
United States
Diana
$222 nightly
The price is $259
Jul 5 - Jul 6
Total with taxes and fees
Staypineapple, A Delightful Hotel, South End
Lobby sitting area

The Revolution Hotel

The Revolution Hotel
3.5 star property
South End
9.0 out of 10, Wonderful, (2,651 reviews)
"Great location and easy check in."
United States
Jeff
$137 nightly
The price is $159
Jun 7 - Jun 8
Total with taxes and fees
The Revolution Hotel
Front of property

The Hotel Marblehead

The Hotel Marblehead
3.5 star property
Marblehead
9.2 out of 10, Wonderful, (503 reviews)
"Clean room and comfortable beds!"
United States
Adam
$220 nightly
The price is $245
Jun 7 - Jun 8
Total with taxes and fees
The Hotel Marblehead
Lobby

Aloft by Marriott Boston Seaport District

Aloft by Marriott Boston Seaport District
3.0 star property
Seaport District
8.8 out of 10, Excellent, (1,463 reviews)
"Nice hotel within walking distance of attractions."
United States
Angela
$190 nightly
The price is $221
Jul 5 - Jul 6
Total with taxes and fees
Aloft by Marriott Boston Seaport District
Premium bedding, in-room safe, desk, laptop workspace

Courtyard by Marriott Boston Downtown/North Station

Courtyard by Marriott Boston Downtown/North Station
3.0 star property
West End
9.4 out of 10, Exceptional, (1,350 reviews)
"Great location!"
United States
Jody
$195 nightly
The price is $227
Jun 7 - Jun 8
Total with taxes and fees
Courtyard by Marriott Boston Downtown/North Station
Standard Queen Queen Lake View | Individually furnished, desk, laptop workspace, blackout drapes

Lakeside Inn

Lakeside Inn
2.0 star property
Wakefield
7.6 out of 10, Good, (2,359 reviews)
"Lovely hotel. Clean, quiet, helpful staff."
Canada
Charlene
$103 nightly
The price is $115
Jun 8 - Jun 9
Total with taxes and fees
Lakeside Inn
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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Top Winchester Hotel Reviews

Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"It is within expectations."
Hsan-Jan 1-night trip
Posted 3 hours ago
Hyatt Regency Boston/Cambridge

Find out more about Winchester

Winchester Resorts information

Number of reviews
33,783
Accommodation
0 Resorts
Lowest Price
$115
Highest Price
$274

Frequently asked questions

What can I expect from a resort vacation in Winchester?
Expedia can help you browse resorts and other lodging options that provide similar services and comforts. If you have trouble finding a resort in Winchester that works for you, you can use the search page filters to look for hotels, or search for properties that offer amenities like swimming pools or all-inclusive packages. We make it easy to book great accommodations so you can move on to planning your trip itinerary.
What can I do in Winchester?
Winter Pond offers fun for the whole family, while Fenway Park is one of the most popular places to visit nearby. You'll also find top attractions like Encore Boston Harbor and Harvard Square in the area.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall.
What's the best way to get to and around Winchester?
Fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) away from the heart of the city. Otherwise, you can search for flights to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away. To see more of the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station.

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