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

Find Hotels with a Pool in Winchester, MA

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Check availability on Winchester Hotels with a Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 hotel room with a desk, two beds, a TV, a lamp, and a painting on the wall.
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.
$114 nightly
$127 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Plus New Englander
An indoor swimming pool with clear reflections, large windows, and a tiled border.
A hotel lobby with a patterned carpet, seating area with armchairs and sofas, a staircase, and a cityscape painting on the wall.
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.

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.
$122 nightly
$137 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Woburn/Boston North
A modern hotel with a swimming pool, multiple balconies, and a glass facade.
An outdoor seating area with modern furniture and a fire feature.
A modern lounge area with a glass wall, a central fire feature, and seating arrangements.
A modern lobby with a central seating area, a reception desk, and a unique wall display.

3. 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.
$137 nightly
$154 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Boston/Woburn
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 hotel with a covered entrance, multiple floors, and a landscaped area in front.
A modern building with large windows, outdoor seating, and a well-maintained garden.

4. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
  • Splash into seasonal bliss at this refreshing indoor pool oasis with spotless aquatic amenities.
$132 nightly
$148 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Boston Woburn
An indoor swimming pool with lounge chairs and a towel rack.
A banquet hall with round tables, clear chairs, and floral centerpieces.
A living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a kitchen area visible in the background.
A hotel entrance with a glass door, illuminated pillars, and a paved walkway.

5. 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.
$118 nightly
$132 total
Nov 1 - Nov 2
Total with taxes and fees
Crowne Plaza Boston - Woburn by IHG
A swimming pool with clear blue water, surrounded by lounge chairs and a large window.
A modern living room with a flat-screen TV, two blue armchairs, a grey sofa, and a round coffee table.
Exterior
Property entrance

6. 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.
$176 nightly
$197 total
Nov 1 - Nov 2
Total with taxes and fees
Hyatt Place Boston/Medford
An outdoor patio area with a sofa set, a dining table, and a large umbrella.
An outdoor patio with tables and chairs, umbrellas, and potted plants.
A modern reception area with a curved desk, seating, and a large mirror wall.
A modern bar area with a long counter, multiple stools, and a variety of bottles and glasses.

7. Boston Marriott Burlington

Boston Marriott Burlington
Burlington Town Center
  • Dive into dual-pool luxury with indoor and outdoor swimming options at this upscale Boston-area retreat with pool loungers.
$183 nightly
$204 total
Oct 4 - Oct 5
Total with taxes and fees
Boston Marriott Burlington
A swimming pool with lane markers, a blue deck, and yellow sun loungers.
A reception area with a wooden reception desk, a green accent wall, and a patterned rug.
A hotel dining area with wooden tables and chairs, a kitchen in the background, and a blue patterned carpet.
A modern living room with two green sofas, a round coffee table, a stone fireplace, and large windows with sheer curtains.

8. 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.
$125 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn by Marriott Boston Woburn-Burlington
An outdoor patio area with a stone fire pit, wicker furniture, and a pergola.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and potted plants.
A modern kitchen with built-in appliances, a flat-screen TV, and a variety of storage cabinets.
A buffet setup with various food items and containers.

9. 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.
$139 nightly
$155 total
Nov 1 - Nov 2
Total with taxes and fees
HYATT house Boston/Burlington
A swimming pool with clear water, surrounded by lounge chairs and a view of trees through large windows.
A modern breakfast buffet with a marble island, glass display cases, and a variety of food and drink options.
An outdoor seating area with wicker furniture and a central fire feature, adjacent to a modern building with large windows.
A modern bar area with a central island, bar stools, and a chandelier.

10. AC Hotel by Marriott Boston Cambridge

AC Hotel by Marriott Boston Cambridge
North Cambridge
  • Refreshing indoor pool oasis creates year-round aquatic paradise in this Boston area gem.
$173 nightly
$201 total
Nov 1 - Nov 2
Total with taxes and fees
AC Hotel by Marriott Boston Cambridge
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Choose what matters most at hotels with a pool in Winchester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Winchester Hotel Reviews

Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

10/10 Excellent
"I had a wonderful stay at this property in Morristown. The location was perfect for exploring the area, and the accommodations were clean and comfortable. I would definitely recommend it to other travelers!"
Diwakar 1-night trip
Posted 1 hour ago
Hilton Garden Inn Tewksbury Andover
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Very helpful staff"
Brett Tyson 5-night trip
Posted 2 hours ago
Hyatt Regency Boston/Cambridge
Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"It was in a great location. They stored our bags before check in and the bed was reasonably comfy."
Dallin 2-night trip
Posted 8 hours ago
Harborside Inn Of Boston
The Dagny Boston

The Dagny Boston

10/10 Excellent
"Great hotel and great city."
David 4-night trip
Posted 1 day ago
The Dagny Boston
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"I love the location and the dining options."
Run 1-night trip
Posted 2 days ago
Hyatt Regency Boston Harbor

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.

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