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

Top Winchester Hotels with Swimming Pool

Indoor pool
Aloft by Marriott, Boston Seaport District

Aloft by Marriott, Boston Seaport District

3.0 star property
Seaport District
  • Indoor pool
  • Near the beach
9.0 out of 10, Wonderful, (1362)
Swimming continues regardless of weather in the pristine indoor pool, open from early morning until late evening. Minutes from Flynn Cruiseport and the Children's Museum, this hotel balances aquatic relaxation with urban adventure.
The price is P6,718
P9,538 total
includes taxes & fees
Dec 14 - Dec 15
Aloft by Marriott, Boston Seaport District
Indoor pool
Hampton Inn Boston Seaport District

Hampton Inn Boston Seaport District

3.0 star property
Seaport District
  • Indoor pool
9.2 out of 10, Wonderful, (2664)
Swimming enthusiasts appreciate the immaculate indoor pool that offers year-round relaxation regardless of weather. Just steps from Flynn Cruiseport and the Convention Center, this hotel combines aquatic enjoyment with a 24-hour fitness center for complete wellness.
The price is P7,024
P8,180 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn Boston Seaport District
Indoor pool
The Westin Boston Seaport District

The Westin Boston Seaport District

4.0 star property
Seaport District
  • Indoor pool
  • Near the beach
  • Hot tub
9.2 out of 10, Wonderful, (2283)
Swimming enthusiasts discover aquatic bliss in the indoor pool and soothing hot tub, creating perfect relaxation after exploring Boston Harbor attractions. Guests appreciate the 24-hour fitness center with Peloton bikes before enjoying meals at the on-site café.
The price is P7,372
P10,643 total
includes taxes & fees
Nov 23 - Nov 24
The Westin Boston Seaport District
Indoor pool
Hyatt Regency Boston

Hyatt Regency Boston

4.0 star property
Downtown Boston
  • Indoor pool
9.0 out of 10, Wonderful, (1680)
Aquatic relaxation awaits at this urban sanctuary where the indoor pool complements a well-equipped health club. Surrounded by Boston's prime attractions, the hotel balances sightseeing adventures with peaceful poolside moments.
The price is P8,426
P11,875 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Regency Boston
Indoor pool
Hampton Inn & Suites Boston Crosstown Center

Hampton Inn & Suites Boston Crosstown Center

3.0 star property
South End
  • Indoor pool
7.8 out of 10, Good, (1384)
Aquatic relaxation awaits year-round at the indoor pool, open from 8:00 AM to 8:00 PM. After swimming laps, guests can energize in the fitness center or savor the complimentary breakfast buffet before exploring nearby Northeastern University.
The price is P5,138
P5,984 total
includes taxes & fees
Nov 30 - Dec 1
Hampton Inn & Suites Boston Crosstown Center
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
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (1938)
Splash into the heated outdoor pool, a relaxing oasis complemented by comfortable loungers and a poolside bar. Nearby Fenway Park and Boston's cultural attractions await after enjoying the hotel's unique vinyl record players in each spotless room.
The price is P4,909
P8,461 total
includes taxes & fees
Nov 25 - Nov 26
The Verb Hotel
Indoor pool, open 6:00 AM to 11:00 PM, sun loungers
Boston Marriott Copley Place

Boston Marriott Copley Place

4.0 star property
Back Bay
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1715)
Nestled within the urban retreat, an indoor pool beckons with loungers creating an oasis after exploring Boston landmarks. Guests appreciate extended 6:00 AM to 9:30 PM hours, complimenting the 24-hour fitness center and on-site shopping.
The price is P8,839
P12,352 total
includes taxes & fees
Nov 25 - Nov 26
Boston Marriott Copley Place
Indoor pool
Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District

3.0 star property
Seaport District
  • Indoor pool
9.2 out of 10, Wonderful, (1349)
Swimming enthusiasts relish the pristine indoor pool at this waterfront haven, complementing invigorating workouts in the modern fitness center. Spotless accommodations feature full kitchens, while complimentary breakfast energizes guests before exploring nearby Flynn Cruiseport.
The price is P7,260
P8,345 total
includes taxes & fees
Dec 14 - Dec 15
Homewood Suites by Hilton Boston Seaport District
Indoor pool
Renaissance® Boston Seaport District

Renaissance® Boston Seaport District

4.0 star property
Seaport District
  • Indoor pool
  • Near the beach
9.0 out of 10, Wonderful, (1004)
Refreshing waters await in the serene indoor pool, complemented by a rejuvenating sauna and 24-hour fitness center. After swimming, guests savor excellent cuisine at the hotel restaurant while enjoying convenient access to Boston's premier attractions.
The price is P7,955
P11,665 total
includes taxes & fees
Nov 23 - Nov 24
Renaissance® Boston Seaport District
Indoor pool
Element by Marriott, Boston Seaport District

Element by Marriott, Boston Seaport District

3.0 star property
Seaport District
  • Indoor pool
  • Near the beach
9.0 out of 10, Wonderful, (1000)
Sparkling waters beckon in the indoor pool, offering year-round swimming after exploring Boston's cultural attractions. Complimentary bicycles provide scenic waterfront transportation, while evening piano music creates memorable nights.
The price is P6,953
P9,570 total
includes taxes & fees
Nov 23 - Nov 24
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.
View all properties

Top Winchester Hotel Reviews

The Dagny Boston

The Dagny Boston

10/10 Excellent
"Awsome hotel"
Torkild 4-night trip
Posted 20 hours ago
The Dagny Boston

Explore a world of travel with Expedia

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. The Revolution Hotel: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool, and a full-service spa. CitizenM Boston North Station: Hotel located near Revere Beach. Provides daily, an indoor pool, and complimentary wired internet access. Omni Boston Hotel at the Seaport: Hotel, 2-minute walk from Massachusetts General Hospital. Features complimentary wireless internet access, a seasonal outdoor pool, and a 24-hour fitness center. The Dagny Boston: Hotel located near Faneuil Hall Marketplace. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions.
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.