Search Hotels with Pool in Winchester

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Check availability on Winchester Hotels with Pool

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

Our top choices for Winchester hotels with a pool

Indoor pool
Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District
3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1387)
"Room was nice and clean reception staff was very friendly."
United States
Ede
The price is Rp1.724.323
Rp2.495.305 total
includes taxes & fees
29 Dec - 30 Dec
Aloft by Marriott, Boston Seaport District
Indoor pool
Hyatt Regency Boston

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1730)
"Amazing room, friendly staff"
United States
Ryan
The price is Rp2.169.634
Rp3.112.473 total
includes taxes & fees
29 Dec - 30 Dec
Hyatt Regency Boston
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, pool loungers
The Verb Hotel

The Verb Hotel

The Verb Hotel
3.5 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (1967)
"Breakfast very limited, but otherwise nice place to stay."
United States
Gemma
The price is Rp1.491.623
Rp2.516.791 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Verb Hotel
Indoor pool
Element by Marriott, Boston Seaport District

Element by Marriott, Boston Seaport District

Element by Marriott, Boston Seaport District
3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1001)
"Everything about the hotel was great and will be staying again "
United States
Zuri
The price is Rp1.724.323
Rp2.426.499 total
includes taxes & fees
29 Dec - 30 Dec
Element by Marriott, Boston Seaport District
Indoor pool
The Westin Boston Seaport District

The Westin Boston Seaport District

The Westin Boston Seaport District
4.0 star property
Seaport District
9.2 out of 10, Wonderful, (2342)
"Nice hotel and great location."
United States
James Earl
The price is Rp1.992.179
Rp2.904.898 total
includes taxes & fees
29 Dec - 30 Dec
The Westin Boston Seaport District
Outdoor pool, pool loungers
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport
5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4336)
"Great location "
United States
Karen
The price is Rp2.397.445
Rp3.474.188 total
includes taxes & fees
2 Jan - 3 Jan 2026
Omni Boston Hotel at the Seaport
Indoor pool
Renaissance® Boston Seaport District

Renaissance® Boston Seaport District

Renaissance® Boston Seaport District
4.0 star property
Seaport District
9.0 out of 10, Wonderful, (1001)
"The room is so clean the hotel is beautiful the restaurant is amazing the service amazing to I recommend 😍"
United States
Marilyn
The price is Rp1.992.655
Rp3.002.974 total
includes taxes & fees
28 Dec - 29 Dec
Renaissance® Boston Seaport District
Indoor pool
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2731)
"Great stay"
United States
Katerina
The price is Rp2.110.540
Rp2.457.664 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn Boston Seaport District
Indoor pool
InterContinental Boston by IHG

InterContinental Boston by IHG

InterContinental Boston by IHG
5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1013)
"Great stay"
United States
Anthony
The price is Rp2.749.709
Rp3.962.412 total
includes taxes & fees
29 Dec - 30 Dec
InterContinental Boston by IHG
Exterior
DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown

DoubleTree by Hilton Boston - Downtown
4.0 star property
Bay Village
8.8 out of 10, Excellent, (1004)
"Clean very nice room amd great staff"
United States
James
The price is Rp1.565.323
Rp1.822.819 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Boston - Downtown
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.
View all properties

Top Winchester Hotel Reviews

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent
"Very conveniently located. Best location if taking Amtrak"
Dunnapar F 2-night trip
Posted 3 days ago
The Westin Copley Place, Boston, a Marriott Hotel

Frequently asked questions

What are some accommodation options with pools in Winchester?
Harborside Inn Of Boston: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Provides 4 restaurants, an outdoor pool and a full-service spa. Hilton Boston Back Bay: Hotel, 9-minute walk from Boston Convention and Exhibition Center. Offers 2 restaurants, an indoor pool and a health club. Omni Boston Hotel at the Seaport: Hotel, 7-minute walk from New England Aquarium. Features a sauna, an indoor pool and complimentary high-speed (wired) Internet access. CitizenM Boston North Station: Hotel located near New England Aquarium. Offers a 24-hour fitness centre, an indoor pool and flat-screen televisions. Seaport Hotel Boston: Hotel, 2-minute walk from Boston Harbor. Features a snack bar/deli, an indoor pool and complimentary wireless Internet access.
What is there to see and do in Winchester?
While you're in the area, consider exploring places such as Fenway Park, Encore Boston Harbor and Harvard Square. Take in the natural beauty with a stop at Winter Pond.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider accommodation with an outdoor swimming pool if you're planning to visit Winchester in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temp is 0°C.
What's the best way to travel around Winchester?
Knowing the transportation options in Winchester can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station. Winchester may not have many public transport options to choose from, so consider a car rental to maximise your time.