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
Aug 19 - Aug 20
Tomorrow
Aug 20 - Aug 21
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Winchester hotels with a pool

Indoor pool
Breakfast area
Standard Room, 2 Queen Beds, Non Smoking, Refrigerator
Exterior

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.
$118 nightly
$132 total
Aug 23 - Aug 24
Total with taxes and fees
Best Western Plus New Englander
Pool
Ballroom
Meeting facility
Exterior

2. 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.
$114 nightly
$127 total
Sep 7 - Sep 8
Total with taxes and fees
Crowne Plaza Boston - Woburn by IHG
Pool
Bar (on property)
Lobby sitting area
Bar (on property)

3. 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.
$127 nightly
$141 total
Aug 30 - Aug 31
Total with taxes and fees
Courtyard by Marriott Woburn/Boston North
Pool
Exterior
Room
Room

4. 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.
$135 nightly
$151 total
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Place Boston/Medford
Pool
Exterior
Terrace/patio
Bar (on property)

5. 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.
$130 nightly
$146 total
Aug 28 - Aug 29
Total with taxes and fees
Hilton Boston/Woburn
Pool
Exterior
Terrace/patio
Lobby

6. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
  • Splash into seasonal bliss at this refreshing indoor pool oasis with spotless aquatic amenities.
$131 nightly
$147 total
Aug 30 - Aug 31
Total with taxes and fees
Hampton Inn Boston Woburn
Terrace/patio
Terrace/patio
Reception
Bar (on property)

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.
$135 nightly
$151 total
Aug 28 - Aug 29
Total with taxes and fees
Boston Marriott Burlington
Outdoor pool
Lobby
Lobby
Breakfast meal

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.
$116 nightly
$130 total
Aug 24 - Aug 25
Total with taxes and fees
Fairfield Inn by Marriott Boston Woburn-Burlington
Pool
Exterior
Suite, 2 Bedrooms
Exterior

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
Sep 7 - Sep 8
Total with taxes and fees
HYATT house Boston/Burlington
Pool
Lobby
Exterior
Terrace/patio

10. 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.
$141 nightly
$158 total
Aug 28 - Aug 29
Total with taxes and fees
Homewood Suites by Hilton Boston Woburn
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

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

10/10 Excellent
"The hotel check in process was a "self check in" with the help of a very pleasant and helpful staff member. The room was clean. Bathroom a bit industrial with the makeup mirror directly over the toilet. Could have used a refrigerator. Overall very pleasant place and convenient to Fanuel Hall and North End."
Thomas 2-night trip
Posted 2 hours ago
Club Quarters Hotel Faneuil Hall, Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Great hotel with nice amenities and friendly staff that are accommodating. Will definitely be back!"
Stephen 2-night trip
Posted 3 hours ago
Hyatt Regency Boston/Cambridge
Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Great staff, warm and welcoming, perfect location! We stay at boutique hotels while frequently traveling in Europe. This is just what we were looking - a continental experience but so close to home."
Ted 1-night trip
Posted 4 hours ago
Harborside Inn Of Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"C’est vraiment un très bon choix pour le prix. L’hôtel est vraiment bien situé dans un quartier super agréable et il y a plusieurs choses à voir et à faire à proximité. Le déjeuner est plutôt nul et consiste en café, jus d’orange Tropicana, pomme et une patisserie beaucoup trop sucrée pour le déjeuner mais, c’est quand même mieux que rien ! Les chambres sont belles et spacieuses. Nous retournerons à cet hôtel sans hésiter."
Karine 2-night trip
Posted 17 hours ago
The Midtown Hotel MOD Collection by Sonesta
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

10/10 Excellent
"Great"
Kevin 1-night trip
Posted 20 hours ago
Wyndham Boston Beacon Hill

Frequently asked questions

What are some accommodations with pools in Winchester?
Seaport Hotel Boston: Hotel, 9-minute walk from Boston Convention and Exhibition Center. 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, 3-minute walk from Boston Convention and Exhibition Center. Offers 2 bars, an indoor pool, and a snack bar/deli. The Dagny Boston: Hotel located near Encore Boston Harbor. Features a snack bar/deli, an indoor pool, and complimentary wireless internet access. The Midtown Hotel MOD Collection by Sonesta: Hotel, 1-minute walk from Massachusetts General Hospital. Offers complimentary wireless internet access, a seasonal outdoor pool, and a 24-hour fitness center.
What is there to see and do in Winchester?
While you're in the area, consider exploring places like TD Garden, Fenway Park, and Encore Boston Harbor. Make a point to visit attractions like Griffin Photography Museum and 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.

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