Find Hotels with a Pool in Winchester, MA

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Check availability on Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

Indoor pool
Hyatt Regency Boston

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1699)
"Convenient location to mass transit "
United States
todd
The price is NT$3,793
NT$5,509 total
includes taxes & fees
Dec 14 - Dec 15
Hyatt Regency Boston
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, (1372)
"Room was nice and clean reception staff was very friendly."
United States
Ede
The price is NT$3,213
NT$4,650 total
includes taxes & fees
Dec 21 - Dec 22
Aloft by Marriott, Boston Seaport District
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 NT$3,962
NT$5,885 total
includes taxes & fees
Dec 19 - Dec 20
Renaissance® 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, (2320)
"Nice hotel and great location."
United States
James Earl
The price is NT$3,527
NT$5,197 total
includes taxes & fees
Dec 22 - Dec 23
The Westin Boston Seaport District
Indoor pool
Seaport Hotel Boston

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (3796)
"Great weekend stay!"
United States
Amanda
The price is NT$4,505
NT$5,402 total
includes taxes & fees
Dec 16 - Dec 17
Seaport Hotel Boston
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, (2701)
"Good room, fantastic breakfast all very clean."
United States
Andres
The price is NT$3,932
NT$4,579 total
includes taxes & fees
Jan 1 - 2026/1/2
Hampton Inn Boston Seaport District
Courtyard
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, (1002)
"Clean very nice room amd great staff"
United States
James
The price is NT$2,788
NT$3,247 total
includes taxes & fees
Jan 4 - 2026/1/5
DoubleTree by Hilton Boston - Downtown
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers
The Verb Hotel

The Verb Hotel

The Verb Hotel
3.5 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (1949)
"Breakfast very limited, but otherwise nice place to stay."
United States
Gemma
The price is NT$3,060
NT$5,017 total
includes taxes & fees
Jan 1 - 2026/1/2
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, (1000)
"Room was clean and comfortable. Staff was friendly and helpful."
United States
Michael
The price is NT$3,088
NT$4,376 total
includes taxes & fees
Dec 21 - Dec 22
Element by Marriott, 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, (1003)
"Room was clean, loved the pool, and the food was delicious! "
United States
Heather
The price is NT$5,241
NT$7,520 total
includes taxes & fees
Dec 22 - Dec 23
InterContinental Boston by IHG
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

The Dagny Boston

The Dagny Boston

10/10 Excellent
"We intentionally stay at the Dagny Boston for so many reasons, but top of my list is the absolutely delightful friendliness we experience with EVERYONE on staff at the hotel. From being greeted at the door in arrival to the smiles from housekeeping staff, everyone is WONDERFUL!!! Thank you so much for a fabulous stay!!!!"
Megan 2-night trip
Posted 1 day ago
The Dagny Boston

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Frequently asked questions

What are some accommodations with pools in Winchester?
Seaport Hotel Boston: Hotel, 9-minute walk from Boston Convention and Exhibition Center. Features 2 restaurants, an indoor pool, and a health club. Omni Boston Hotel at the Seaport: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Offers 4 restaurants, an outdoor pool, and a full-service spa. CitizenM Boston North Station: Hotel, 7-minute walk from New England Aquarium. Features a sauna, an indoor pool, and complimentary wired internet access. Harborside Inn Of Boston: Hotel located near New England Aquarium. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. The Revolution Hotel: Hotel, 2-minute walk from Massachusetts General Hospital. Features complimentary wireless internet access, a seasonal outdoor pool, and a 24-hour fitness center.
What is there to see and do in Winchester?
While you're in the area, consider exploring places like Fenway Park, Harvard Square, and TD Garden. 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 an accommodation that has an outdoor pool if you will be visiting Winchester in the hottest months of July, August, or June when the average temperature is 69°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or December when the average temp is 33°F.
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 explore the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station. Winchester might not have many public transit options to choose from so consider a car rental to maximize your time.