A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Hotels with Swimming Pool in Winchester, Boston

  • 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

Tonight
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Winchester hotels with a pool

An indoor swimming pool with a tiled ceiling, lounge chairs, and a view of the outdoors.
A modern hotel lobby with a seating area featuring blue upholstered sofas, a coffee table with a vase of flowers, and a large flat-screen TV mounted on a dark wall.
A modern hotel entrance with a covered walkway, a glass facade, and a landscaped area with shrubs and trees.
A modern restaurant with a central counter, multiple dining tables, and chairs.

1. Best Western Plus New Englander

Best Western Plus New Englander
Woburn
  • Modern hotel offers year-round indoor swimming, unaffected by New England's seasonal changes.
P7,131
P7,966 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus New Englander
An indoor swimming pool with clear reflections, large windows, and a tiled border.
A hotel lobby with a staircase, seating area, and patterned carpet.
A modern bar area with a large TV, a fireplace, and a patterned carpet.
A hotel lobby with a patterned carpet, seating area with armchairs and sofas, a staircase, and a cityscape painting on the wall.

2. Courtyard by Marriott Woburn/Boston North

Courtyard by Marriott Woburn/Boston North
Woburn
  • Splash into year-round bliss at this Woburn hotel with an indoor pool for anytime swimming.
P7,689
P8,589 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Woburn/Boston North
Pool
A modern living room with a flat-screen TV, two blue armchairs, a grey sofa, and a round coffee table.
A conference room with rows of chairs, a projection screen displaying 'HYATT PLACE', and a large window with curtains.
A bar area with a granite countertop, bar stools, a coffee machine, and shelves with bottles and glasses.

3. Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
Medford
  • Splash into serene poolside bliss with a year-round indoor swimming haven at this Boston-area retreat.
P8,732
P9,754 total
includes taxes & fees
Nov 11 - Nov 12
Hyatt Place Boston/Medford
An indoor swimming pool with clear glass walls, wooden flooring, and blue chairs along the side.
A modern kitchen with a bar area, bar stools, pendant lighting, and a large TV.
A modern building with large windows, outdoor seating, and a well-maintained garden.
A modern hotel room with a sectional sofa, armchairs, a flat-screen TV, and large windows with curtains.

4. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
  • Splash into seasonal bliss at this refreshing indoor pool oasis with spotless aquatic amenities.
P8,088
P9,034 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn Boston Woburn
An indoor swimming pool with clear glass walls, wooden paneling, and blue chairs along the side.
A modern hotel lobby with a large sofa, ottomans, a fireplace, and a TV mounted on the wall.
A modern outdoor patio with a wooden table, chairs, a grill, and a pergola.
A modern hotel with a central courtyard, multiple floors, and a flagpole.

5. Homewood Suites by Hilton Boston Woburn

Homewood Suites by Hilton Boston Woburn
Woburn
  • Dip into refreshing relaxation with an indoor pool, 24-hour fitness center, and BBQ area.
P8,916
P9,959 total
includes taxes & fees
Nov 8 - Nov 9
Homewood Suites by Hilton Boston Woburn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with multiple windows.
A conference room with multiple tables and chairs, equipped with water bottles and a projector screen.
A modern dining area with a mix of seating options including tables, chairs, and a bench.
A gym with treadmills, elliptical machines, and dumbbells.

6. HYATT house Boston/Burlington

HYATT house Boston/Burlington
Burlington
  • Splash into summer fun with a seasonal outdoor pool and explore Boston's attractions from this suburban hotel's convenient locale.
P8,732
P9,754 total
includes taxes & fees
Nov 1 - Nov 2
HYATT house Boston/Burlington
An indoor swimming pool with lounge chairs and a towel rack.
A banquet hall with round tables, clear chairs, and floral centerpieces.
A hotel entrance with a glass door, illuminated pillars, and a paved walkway.
A buffet area with various food options, including fruits, vegetables, and prepared dishes.

7. Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
Woburn
  • Dive into year-round swimming at this hotel's indoor pool, open until 10 PM daily for refreshing aquatic escapes.
P7,162
P7,999 total
includes taxes & fees
Nov 9 - Nov 10
Crowne Plaza Boston - Woburn by IHG
A modern hotel with a swimming pool, multiple balconies, and a glass facade.
A modern bar area with a long counter, multiple bar stools, and a variety of bottles and glasses on shelves.
An outdoor seating area with modern furniture and a fire feature.
A modern lobby with a central seating area, a reception desk, and a unique wall display.

8. Hilton Boston/Woburn

Hilton Boston/Woburn
Woburn
  • Splash into a year-round aquatic retreat at this Boston-area hotel with an indoor pool and inviting terrace lounge.
P8,490
P9,484 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Boston/Woburn
An indoor swimming pool with lounge chairs and a view of the outside.
A modern kitchen with a central island, bar stools, and a dining area with chairs.
A modern kitchen with a large island, bar stools, and a dining table.
A multi-story hotel with a brick facade, multiple windows, and a visible entrance.

9. Residence Inn by Marriott Boston Burlington

Residence Inn by Marriott Boston Burlington
Burlington
  • Splash into refreshing relaxation with an indoor pool and hot tub at this Burlington hotel, steps from premium shopping.
P10,931
P12,210 total
includes taxes & fees
Nov 6 - Nov 7
Residence Inn by Marriott Boston Burlington
A swimming pool with lane markers, a blue deck, and yellow sun loungers.
A hotel dining area with wooden tables and chairs, a kitchen in the background, and a blue patterned carpet.
A stone fireplace with a black shelf, a large window with a forest view, and a dining area with wooden furniture.
A reception area with a wooden reception desk, a green accent wall, and a patterned rug.

10. Fairfield Inn by Marriott Boston Woburn-Burlington

Fairfield Inn by Marriott Boston Woburn-Burlington
Woburn
  • Dive into a refreshing poolside escape at this Woburn-Burlington hotel, where summer days unfold at the seasonal outdoor oasis.
P6,888
P7,694 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn by Marriott Boston Woburn-Burlington
View all properties

Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Great location close to historic sites and easy access to the T. Well maintained and clean property and room."
Johnathan 4-night trip
Posted less than an hour ago
Harborside Inn Of Boston
Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Location to airport and cruise ships. Local bars and restaurants"
Patricia 1-night trip
Posted less than an hour ago
Seaport Hotel Boston
Hyatt Regency Boston

Hyatt Regency Boston

10/10 Excellent
"Great hotel. Close to the Macy and downtown Boston."
Robert 4-night trip
Posted 5 hours ago
Hyatt Regency Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"Clean room. Comfy beds and pillows. Bathroom fans were super loud in our room. Convenient walking distance everywhere. Use bus or subway to get around. A reflection pool across street. Limited junk pre packaged items for breakfast. These will quickly raise your blood sugar. Room has fridge, hair dryer. Too expensive but offered little amenity. They were updating hall carpets. A convenient filtered water refill station near the main lobby. They charge you for parking."
thomas 3-night trip
Posted 18 hours ago
The Midtown Hotel MOD Collection by Sonesta
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent
"10/10 stay!"
Mary 2-night trip
Posted 2 days ago
The Westin Copley Place, Boston, a Marriott Hotel

Frequently asked questions

What are some accommodations 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. Seaport Hotel Boston: Hotel, 9-minute walk from Boston Convention and Exhibition Center. Offers 2 restaurants, an indoor pool, and a health club. The Revolution Hotel: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Features 2 bars, an indoor pool, and a snack bar/deli. Hilton Boston Park Plaza: Provides free self parking, an indoor pool, and complimentary wireless internet access. The Dagny Boston: Hotel, 12-minute walk from Massachusetts Institute of Technology. Offers a snack bar/deli, an indoor pool, and complimentary wireless internet access.
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. Make a point to visit attractions like Winter Pond and Griffin Photography Museum.
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