TOP Hotels with Pool in Winchester, MA for 2026

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

Harborside Inn Of Boston : Hotel, 4-minute walk from Boston Harbor. Provides a sauna, an indoor pool and complimentary high-speed (wired) Internet access. The Revolution Hotel : Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool and a full-service spa. The Langham, Boston : 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 located near New England Aquarium. Provides 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

Brad

฿4,725 total

includes taxes & fees

22 Feb - 23 Feb

Hyatt Regency Boston

Downtown Boston

Yohlman

฿5,812 total

includes taxes & fees

23 Feb - 24 Feb

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

The Verb Hotel

Fenway–Kenmore

julie

฿4,676 total

includes taxes & fees

23 Feb - 24 Feb

Omni Boston Hotel at the Seaport

Seaport District

Suzanne

฿5,938 total

includes taxes & fees

1 Mar - 2 Mar

The Westin Boston Seaport District

Seaport District

Monique

฿7,208 total

includes taxes & fees

22 Feb - 23 Feb

Aloft by Marriott, Boston Seaport District

Seaport District

Bianca

฿4,709 total

includes taxes & fees

8 Mar - 9 Mar

Sonesta Select Boston Danvers

Danvers

Kevin

฿3,509 total

includes taxes & fees

2 Mar - 3 Mar

Boston Marriott Long Wharf

North End

Lida

฿6,807 total

includes taxes & fees

1 Mar - 2 Mar

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Top Winchester Hotel Reviews

The Dagny Boston

10/10 Excellent

"The service was phenomenal. I’ve stayed at so many hotels/resorts this hotels service stood out to me. They went above & beyond to make us feel welcome & comfortable. The property location was perfect for walking downtown. The cafe wasn’t great despite the good reviews but everything else was 5/5 stars for me & my family. "

Frequently asked questions

What are some accommodation options with pools in Winchester?

Harborside Inn Of Boston: Hotel, 4-minute walk from Boston Harbor. Provides a sauna, an indoor pool and complimentary high-speed (wired) Internet access. The Revolution Hotel: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Features 4 restaurants, an outdoor pool and a full-service spa. The Langham, Boston: 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 located near New England Aquarium. Provides 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 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 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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