Find Casinos in Winchester, MA

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Check availability on Winchester Casinos

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Winchester hotels with a casino

Standard Room, 1 Queen Bed | Premium bedding, in-room safe, iron/ironing board, free WiFi
Found Hotel Boston Common

Found Hotel Boston Common

Found Hotel Boston Common
2.5 star property
Bay Village
8.2 out of 10, Very Good, (1272)
"The room and the staff were very nice. "
United States
Moritz
The price is NT$2,957
NT$3,444 total
includes taxes & fees
Jan 25 - 2026/1/26
Found Hotel Boston Common
Exterior
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel
4.0 star property
Back Bay
8.6 out of 10, Excellent, (3899)
"Was perfect for my overnight stay in Boston and close to public transportation, Boston Common and Newburry Street!"
United States
Dawn
The price is NT$2,641
NT$3,076 total
includes taxes & fees
Dec 28 - Dec 29
Copley Square Hotel, a FOUND Hotel
Meeting facility
Moxy Boston Downtown

Moxy Boston Downtown

Moxy Boston Downtown
3.5 star property
Bay Village
8.8 out of 10, Excellent, (1006)
"Great amenities and staff- perfect location "
United States
Molly
The price is NT$2,483
NT$4,173 total
includes taxes & fees
Jan 4 - 2026/1/5
Moxy Boston Downtown
Exterior
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill
3.5 star property
West End
7.8 out of 10, Good, (2047)
"Amazing stay "
United States
Tia
The price is NT$4,215
NT$4,909 total
includes taxes & fees
Dec 29 - Dec 30
Wyndham Boston Beacon Hill
Reception
Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront
4.5 star property
North End
8.8 out of 10, Excellent, (1741)
"Everything was wonderful! Had a great stay!"
United States
Melody
Battery Wharf Hotel, Boston Waterfront
Restaurant
Hampton Inn & Suites Boston Crosstown Center

Hampton Inn & Suites Boston Crosstown Center

Hampton Inn & Suites Boston Crosstown Center
3.0 star property
South End
7.8 out of 10, Good, (1461)
"Clean room, polite staff and good breakfast. "
United States
Gunish
The price is NT$2,810
NT$3,272 total
includes taxes & fees
Jan 4 - 2026/1/5
Hampton Inn & Suites Boston Crosstown Center
Lobby
Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport

Comfort Inn & Suites Logan International Airport
2.5 star property
Revere
9.0 out of 10, Wonderful, (2215)
"The room was spotless, and the service was very friendly and very easy to check in."
United States
Rodrigo
The price is NT$3,109
NT$3,661 total
includes taxes & fees
Jan 18 - 2026/1/19
Comfort Inn & Suites Logan International Airport
Free daily continental breakfast
avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG

avid hotel Boston Logan Airport - Revere by IHG
2.5 star property
Revere
9.0 out of 10, Wonderful, (1489)
"Excellent amenities, welcoming staff, comfortable beds and a great breakfast!"
United States
Wendy
The price is NT$3,047
NT$3,403 total
includes taxes & fees
Dec 28 - Dec 29
avid hotel Boston Logan Airport - Revere by IHG
Exterior
SpringHill Suites by Marriott Boston Peabody

SpringHill Suites by Marriott Boston Peabody

SpringHill Suites by Marriott Boston Peabody
3.0 star property
Peabody
7.8 out of 10, Good, (1121)
"Clean room, friendly staff, and lots of amenities."
United States
Rachel
The price is NT$2,645
NT$2,955 total
includes taxes & fees
Jan 11 - 2026/1/12
SpringHill Suites by Marriott Boston Peabody
Exterior
The Newbury Boston

The Newbury Boston

The Newbury Boston
5.0 star property
Back Bay
9.2 out of 10, Wonderful, (552)
"Excellent hotel. "
United Kingdom
Anne
The price is NT$11,432
NT$14,960 total
includes taxes & fees
Dec 29 - Dec 30
The Newbury Boston
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

Frequently asked questions

Searching for casino hotels in Winchester?
You might be interested in the area's popular sights, which include Fenway Park, Encore Boston Harbor, and Harvard Square.
When should I take my casino trip to Winchester?
You might spend a lot of your vacation inside, but if you're planning to venture beyond the casino, taking a look at local weather data can help you. 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 is there to do in Winchester?
You can head to Harvard Square, Burlington Mall, or Assembly Row to shop for the perfect souvenir. Check out Somerville Theatre, Harvard Museum of Natural History, or American Repertory Theater for a taste of local culture. If you're looking to add to your itinerary, you can also visit Winter Pond and Middlesex Fells Reservation.
What are my transportation options for my casino getaway to Winchester?
Getting around Winchester is easier with these transportation options: You can book a flight to the closest airport, which is Bedford, MA (BED-Laurence G. Hanscom Field), located 7.7 mi (12.3 km) from the city center. To see more of the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station.

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