TOP Hotels with Pool in Winchester, MA for 2026

Q: What are some accommodation options with pools in Winchester?

Omni Boston Hotel at the Seaport : Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool and a full-service spa. Hilton Boston Park Plaza : Hotel, 11-minute walk from Boston Harbor. Provides 2 restaurants, an indoor pool and a health club. Seaport Hotel Boston : Hotel located near New England Aquarium. Offers a 24-hour fitness centre, an indoor pool and flat-screen televisions. Harborside Inn Of Boston : Hotel, 4-minute walk from Hynes Convention Center. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions. The Dagny Boston : Hotel, 5-minute walk from Boston Common. Features a health club, an indoor pool and a snack bar/deli.

Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA.

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Our top choices for Winchester hotels with a pool

Seaport Hotel Boston

Seaport District

Ettore

Rp3.098.348 total

includes taxes & fees

5 Apr - 6 Apr

Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, pool loungers

The Verb Hotel

Fenway–Kenmore

Chad

Rp4.159.734 total

includes taxes & fees

13 Apr - 14 Apr

Hyatt Regency Boston

Downtown Boston

Alina

Rp3.446.135 total

includes taxes & fees

5 Apr - 6 Apr

Sonesta Select Boston Danvers

Danvers

Iola

Rp2.287.378 total

includes taxes & fees

2 Apr - 3 Apr

Renaissance® Boston Seaport District

Seaport District

Matthew

Rp3.361.489 total

includes taxes & fees

5 Apr - 6 Apr

Omni Boston Hotel at the Seaport

Seaport District

Reza

Rp3.745.982 total

includes taxes & fees

5 Apr - 6 Apr

Hampton Inn Boston Seaport District

Seaport District

Aditya Dadasaheb

Rp2.726.298 total

includes taxes & fees

12 Apr - 13 Apr

Homewood Suites by Hilton Boston Seaport District

Seaport District

Rahul

Rp2.944.951 total

includes taxes & fees

5 Apr - 6 Apr

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Top Winchester Hotel Reviews

Hilton Boston Logan Airport

10/10 Excellent

"Is walking distance to the airport. "

Hyatt Regency Boston/Cambridge

2/10 Terrible

"The experience was terrible. Hotel is so dated and in dire need of a massive overhaul. The restaurant sucks. Front desk is not helpful and needs to be trained properly. The attitude overall is tired and like you’re a nuisance. Arguably one of the worst hotels I stayed at. And it says it’s a 4 star hotel is comical. A 3 star is a stretch. Stay far away. Never again will me or my companies employees stay at Hyatt regency. "

Frequently asked questions

What are some accommodation options with pools in Winchester?

Omni Boston Hotel at the Seaport: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool and a full-service spa. Hilton Boston Park Plaza: Hotel, 11-minute walk from Boston Harbor. Provides 2 restaurants, an indoor pool and a health club. Seaport Hotel Boston: Hotel located near New England Aquarium. Offers a 24-hour fitness centre, an indoor pool and flat-screen televisions. Harborside Inn Of Boston: Hotel, 4-minute walk from Hynes Convention Center. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions. The Dagny Boston: Hotel, 5-minute walk from Boston Common. Features 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 such as 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 accommodation with an outdoor swimming pool if you're planning to visit Winchester in the hottest months of July, August or June, when the average temperature is 21°C. Accommodation with an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temp is 0°C.

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 see more of the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station. Winchester may not have many public transport options to choose from, so consider a car rental to maximise your time.

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