Find Hotels with a Pool in Winchester, MA

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Top Winchester Hotels with a Pool

Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers
The Verb Hotel

The Verb Hotel

3.5 star property
Fenway–Kenmore
9.6 out of 10, Exceptional, (1958)
"Love staying here. Get amenities, clean and great restaurant "
United States
michelle
$118 nightly
The price is $138
Dec 16 - Dec 17
Total with taxes and fees
The Verb Hotel
Indoor pool
Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District

3.0 star property
Seaport District
9.0 out of 10, Wonderful, (1374)
"Room was nice and clean reception staff was very friendly."
United States
Ede
$118 nightly
The price is $138
Dec 21 - Dec 22
Total with taxes and fees
Aloft by Marriott, Boston Seaport District
Indoor pool
InterContinental Boston by IHG

InterContinental Boston by IHG

5.0 star property
Downtown Boston
9.4 out of 10, Exceptional, (1019)
"Beautiful hotel, great location, gracious staff."
United States
Amalia
$167 nightly
The price is $195
Dec 22 - Dec 23
Total with taxes and fees
InterContinental Boston by IHG
Indoor pool
Hyatt Regency Boston

Hyatt Regency Boston

4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1702)
"Great visit, staff very helpful and accommodating!"
United States
Shanae
$157 nightly
The price is $183
Dec 19 - Dec 20
Total with taxes and fees
Hyatt Regency Boston
Indoor pool
The Westin Boston Seaport District

The Westin Boston Seaport District

4.0 star property
Seaport District
9.2 out of 10, Wonderful, (2315)
"Great hotel!"
United States
Eric
$131 nightly
The price is $153
Dec 22 - Dec 23
Total with taxes and fees
The Westin Boston Seaport District
Indoor pool
Seaport Hotel Boston

Seaport Hotel Boston

4.0 star property
Seaport District
9.6 out of 10, Exceptional, (3773)
"Great location and stay!"
United States
Krithika
$153 nightly
The price is $178
Dec 4 - Dec 5
Total with taxes and fees
Seaport Hotel Boston
Indoor pool
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
$120 nightly
The price is $140
Dec 21 - Dec 22
Total with taxes and fees
Element by Marriott, Boston Seaport District
Outdoor pool, sun loungers
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5.0 star property
Seaport District
9.2 out of 10, Wonderful, (4277)
"beautiful hotel "
United States
stacy
$174 nightly
The price is $203
Dec 14 - Dec 15
Total with taxes and fees
Omni Boston Hotel at the Seaport
Indoor pool
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2695)
"Good room, fantastic breakfast all very clean."
United States
Andres
$107 nightly
The price is $125
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Inn Boston Seaport District
Indoor pool
Renaissance® Boston Seaport District

Renaissance® Boston Seaport District

4.0 star property
Seaport District
9.0 out of 10, Wonderful, (1006)
"Nice room and very kind staff!"
United States
Sydney
$170 nightly
The price is $198
Dec 18 - Dec 19
Total with taxes and fees
Renaissance® 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

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"From valet to the front desk staff and the turn down service this is a hotel that will become a go to for our family vacations. Higgly recommend!"
Noelle 2-night trip
Posted 12 hours ago
Seaport Hotel Boston

Frequently asked questions

What are some accommodations with pools in Winchester?
CitizenM Boston North Station: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Offers 4 restaurants, an outdoor pool, and a full-service spa. Omni Boston Hotel at the Seaport: Hotel, 9-minute walk from Boston Convention and Exhibition Center. Offers 2 restaurants, an indoor pool, and a health club. The Revolution Hotel: Hotel located near New England Aquarium. Provides a 24-hour fitness center, an indoor pool, and flat-screen televisions. Harborside Inn Of Boston: Hotel, 10-minute walk from Harvard University. Offers a rooftop terrace, an indoor pool, and a snack bar/deli. Seaport Hotel Boston: 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.

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