Hotels with Swimming Pool in Winchester, Boston

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Swimming Pool

Our top choices for Winchester hotels with a pool

Indoor pool
Seaport Hotel Boston

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (3,885 reviews)
"Great accommodations and friendly staff!"
United States
Nicholas
The price is P7,152
P10,350 total
includes taxes & fees
Jan 18 - Jan 19
Seaport Hotel Boston
Indoor pool
Hyatt Regency Boston

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (1,778 reviews)
"Wonderful stay"
United States
sujata
The price is P7,538
P10,852 total
includes taxes & fees
Jan 31 - Feb 1
Hyatt Regency Boston
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, (1,984 reviews)
"This hotel is quirky and awesome. Loved our stay tremendously. "
United States
Irene
The price is P5,280
P8,909 total
includes taxes & fees
Jan 14 - Jan 15
The Verb Hotel
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, (1,397 reviews)
"Clean room, great bar and breakfast options and good location. "
United States
Bianca
The price is P6,341
P9,109 total
includes taxes & fees
Jan 25 - Jan 26
Aloft by Marriott, Boston Seaport District
Outdoor pool, sun 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, (4,372 reviews)
"Good place to stay "
United States
Richard
The price is P9,268
P13,208 total
includes taxes & fees
Jan 25 - Jan 26
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, (1,001 reviews)
"Staff was very friendly. "
United States
Jean
The price is P7,704
P11,386 total
includes taxes & fees
Jan 19 - Jan 20
Renaissance® Boston Seaport District
Indoor pool
Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (1,415 reviews)
"Clean, good breakfast, location is good too"
United States
Carla
The price is P7,001
P8,048 total
includes taxes & fees
Jan 25 - Jan 26
Homewood Suites by Hilton 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, (2,785 reviews)
"Excellent hotel and stay"
United States
Ana
The price is P7,469
P8,698 total
includes taxes & fees
Jan 25 - Jan 26
Hampton Inn Boston Seaport District
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, (1,001 reviews)
"Everything about the hotel was great and will be staying again "
United States
Zuri
The price is P6,341
P8,865 total
includes taxes & fees
Jan 22 - Jan 23
Element by Marriott, Boston Seaport District
Seasonal outdoor pool, open 10:00 AM to 9:00 PM, pool umbrellas
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill
3.5 star property
West End
7.8 out of 10, Good, (2,050 reviews)
"Great location for a very reasonable price!"
United States
Mark
The price is P7,505
P8,740 total
includes taxes & fees
Feb 1 - Feb 2
Wyndham Boston Beacon Hill
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

Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"Room was clean and staff was friendly!"
Narifa 3-night trip
Posted 2 days ago
Hyatt Regency Boston

Frequently asked questions

What are some accommodations 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. Features 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 wired internet access. Seaport Hotel Boston: Hotel located near New England Aquarium. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. The Dagny Boston: Hotel, 9-minute walk from Boston Common. Offers a health club, an indoor pool, and a snack bar/deli.
What is there to see and do in Winchester?
While you're in the area, consider exploring places like TD Garden, Fenway Park, and Encore Boston Harbor. 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.

Explore a world of travel with Expedia