Find Hotels with a Pool in Winchester, MA

  • 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 a Pool

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Our top choices for Winchester hotels with a pool

Indoor pool

Hyatt Regency Boston

Hyatt Regency Boston
4.0 star property
Downtown Boston
9.0 out of 10, Wonderful, (2,034 reviews)
  • cleanliness
    Swim year-round in Boston's downtown retreat with an indoor pool and wellness amenities.
"The pool is large and a wonderful amenity."
United States
Gail
The price is ₩317,155
₩422,439 total
includes taxes & fees
May 31 - Jun 1
Hyatt Regency Boston
Indoor pool

Seaport Hotel Boston

Seaport Hotel Boston
4.0 star property
Seaport District
9.6 out of 10, Exceptional, (4,367 reviews)
  • cleanliness
    Dive into serenity at this indoor oasis with a steam room and poolside lounging for total aquatic escape.
"We had a great breakfast, had a fun time in the pool, &nice clean room with a view."
United States
Jessica
The price is ₩312,510
₩415,679 total
includes taxes & fees
May 29 - May 30
Seaport Hotel 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, (2,405 reviews)
  • cleanliness
    Dive into aquatic relaxation at this Boston seaport hotel, where an indoor pool and hot tub create a rejuvenating urban oasis.
"The pool was busy but still enjoyable."
United States
Glendaly
The price is ₩408,357
₩546,216 total
includes taxes & fees
Jun 14 - Jun 15
The Westin 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, (4,656 reviews)
  • cleanliness
    Sparkling rooftop pool sanctuary offers skyline views and poolside cocktails at this modern waterfront Boston retreat.
"The pool was an unexpected treat!"
United States
sara
The price is ₩271,934
₩378,523 total
includes taxes & fees
May 29 - May 30
Omni Boston Hotel at the Seaport
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, (2,042 reviews)
  • cleanliness
    Heated outdoor pool becomes an urban oasis at this rock-n-roll hotel near Fenway Park.
"the heated pool was amazing"
United States
Heather
The price is ₩285,439
₩403,078 total
includes taxes & fees
May 31 - Jun 1
The Verb Hotel
Indoor pool

Renaissance® Boston Seaport District

Renaissance® Boston Seaport District
4.0 star property
Seaport District
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Serene indoor pool haven in Boston's Seaport District offers year-round aquatic relaxation.
"The breakfast was great and there was a nice pool for babies there"
Canada
M Mehdi
The price is ₩393,030
₩519,543 total
includes taxes & fees
May 29 - May 30
Renaissance® Boston Seaport District
Seasonal outdoor pool

Sonesta Select Boston Danvers

Sonesta Select Boston Danvers
3.0 star property
Danvers
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Seasonal outdoor pool creates the perfect summer oasis at this clean, comfortable hotel with fitness center and garden setting.
"Beautiful pool."
United States
Mary Linda
The price is ₩210,931
₩235,605 total
includes taxes & fees
May 26 - May 27
Sonesta Select Boston Danvers
Indoor pool

Nantasket Beach Resort

Nantasket Beach Resort
3.0 star property
Nantasket Beach
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Splash year-round at vibrant indoor and outdoor pools with beachfront views at this coastal escape.
"Nice clean room friendly staff beautiful pool"
United States
Victoria
The price is ₩182,842
₩241,524 total
includes taxes & fees
Jun 4 - Jun 5
Nantasket Beach Resort
Indoor pool

DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore
4.0 star property
Danvers
8.2 out of 10, Very Good, (2,435 reviews)
  • cleanliness
    Dive into refreshing relaxation at this hotel's indoor pool sanctuary, complete with sauna, steam room, and massage services.
"Very nice pool area"
United States
Charles
The price is ₩195,756
₩218,655 total
includes taxes & fees
May 27 - May 28
DoubleTree by Hilton Boston North Shore
Indoor pool

Hampton by Hilton at the Boston Seaport District

Hampton by Hilton at the Boston Seaport District
3.0 star property
Seaport District
9.2 out of 10, Wonderful, (2,865 reviews)
  • cleanliness
    Dive into the indoor pool experience at this waterfront hotel, perfect for a refreshing escape after sightseeing in Boston.
"Great indoor pool, excellent breakfast, staff very friendly."
United States
GELVIN
The price is ₩309,932
₩360,920 total
includes taxes & fees
May 31 - Jun 1
Hampton by Hilton at the 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

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Great location , clean and pleasant helpful staff"
Suzanne T. 2-night trip
Posted less than an hour ago
Harborside Inn Of Boston

Frequently asked questions

What are some accommodations with pools in Winchester?
Seaport Hotel Boston: Hotel, 11-minute walk from Boston Harbor. Features 2 restaurants, an indoor pool, and a health club. The Revolution Hotel: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Provides 4 restaurants, an outdoor pool, and a full-service spa. Omni Boston Hotel at the Seaport: Hotel located near New England Aquarium. Features a 24-hour fitness center, an indoor pool, and flat-screen televisions. The Godfrey Hotel Boston: Hotel, 1-minute walk from Massachusetts General Hospital. Features complimentary wireless internet access, a seasonal outdoor pool, and a 24-hour fitness center. Club Quarters Hotel Faneuil Hall, Boston: Hotel, 4-minute walk from Hynes Convention Center. Features 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, 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 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.