Hotels with Pool & Resorts in Winchester from NZ$211

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Check availability on Winchester Hotels with Pool

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 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
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, (2346)
"Nice hotel and great location."
United States
James Earl
The price is NZ$297
includes taxes & fees
29 Dec - 30 Dec
The Westin Boston Seaport District
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 NZ$255
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, (1733)
"Amazing room, friendly staff"
United States
Ryan
The price is NZ$319
includes taxes & fees
30 Dec - 31 Dec
Hyatt Regency Boston
Indoor pool, open 6:00 AM to 11:00 PM, pool loungers
Boston Marriott Copley Place

Boston Marriott Copley Place

Boston Marriott Copley Place
4.0 star property
Back Bay
9.2 out of 10, Wonderful, (1711)
"Clean rooms, helpful and friendly staff"
United States
Tammy
The price is NZ$377
includes taxes & fees
29 Dec - 30 Dec
Boston Marriott Copley Place
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, (2735)
"Great stay"
United States
Katerina
The price is NZ$252
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn Boston Seaport District
Indoor pool, open 5:00 AM to 11:00 PM, pool loungers
Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel

Sheraton Boston, a Marriott Hotel
4.0 star property
Back Bay
8.6 out of 10, Excellent, (1733)
"The staff and the hotel over all is excellent, can’t wait to come back!"
United States
Don
The price is NZ$297
includes taxes & fees
29 Dec - 30 Dec
Sheraton Boston, a Marriott Hotel
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, (1005)
"The room so clean and the staff so nice..I like it."
United States
Sari wijaya
The price is NZ$211
includes taxes & fees
5 Jan - 6 Jan 2026
DoubleTree by Hilton Boston - Downtown
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, (1970)
"Everything about this hotel was wonderful "
United States
Alicia
The price is NZ$258
includes taxes & fees
4 Jan - 5 Jan 2026
The Verb Hotel
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, (4339)
"Staff and room was incredible Def would stay again "
United States
Mark
The price is NZ$356
includes taxes & fees
1 Jan - 2 Jan 2026
Omni Boston Hotel at the Seaport
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 NZ$248
includes taxes & fees
30 Dec - 31 Dec
Element 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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Top Winchester Hotel Reviews

Boston Harbor Hotel

Boston Harbor Hotel

10/10 Excellent
"The whole experience was amazing from the staff assistance to the complementary room upgrade. 10/10 would stay there again. "
Heather 2-night trip
Posted 1 day ago
Boston Harbor 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.