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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with a Pool

Tonight
Sep 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Winchester hotels with a pool

Indoor pool
Exterior
Lobby
Standard Room, 2 Queen Beds, Non Smoking, Refrigerator | Hypo-allergenic bedding available, desk, laptop workspace

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
Sep 7 - Sep 8
Total with taxes and fees
Best Western Plus New Englander
Indoor pool
Lobby sitting area
Bar (on property)
Lobby

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.
$118 nightly
$132 total
Sep 7 - Sep 8
Total with taxes and fees
Courtyard by Marriott Woburn/Boston North
Indoor pool
Lobby
Terrace/patio
Exterior

3. 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
Sep 10 - Sep 11
Total with taxes and fees
Hampton Inn Boston Woburn
Indoor pool
Reception
Bar (on property)
Exterior

4. 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.
$139 nightly
$155 total
Sep 10 - Sep 11
Total with taxes and fees
Hilton Boston/Woburn
Indoor pool
Reception
Exterior
Lobby

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.
$132 nightly
$147 total
Sep 10 - Sep 11
Total with taxes and fees
Homewood Suites by Hilton Boston Woburn
Restaurant
Exterior
Indoor pool
Exterior

6. 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.
$127 nightly
$142 total
Sep 20 - Sep 21
Total with taxes and fees
Crowne Plaza Boston - Woburn by IHG
Seasonal outdoor pool
Lobby
Free daily continental breakfast
Lobby

7. 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
Sep 7 - Sep 8
Total with taxes and fees
Fairfield Inn by Marriott Boston Woburn-Burlington
Indoor pool
Bar (on property)
Premium bedding, down comforters, desk, blackout drapes
Premium bedding, down comforters, desk, blackout drapes

8. 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.
$189 nightly
$211 total
Sep 7 - Sep 8
Total with taxes and fees
Hyatt Place Boston/Medford
Seasonal outdoor pool
Exterior
Suite, 2 Bedrooms | Pillowtop beds, in-room safe, desk, blackout drapes
Bar (on property)

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.
$152 nightly
$170 total
Sep 10 - Sep 11
Total with taxes and fees
HYATT house Boston/Burlington
Seasonal outdoor pool
Lobby
Lobby sitting area
Lobby

10. Lakeside Inn

Lakeside Inn
Wakefield
  • Immerse in lakeside serenity at this welcoming retreat with a sun-drenched seasonal pool offering peaceful water views.
$101 nightly
$113 total
Sep 7 - Sep 8
Total with taxes and fees
Lakeside Inn
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

The Dagny Boston

The Dagny Boston

8/10 Good
"Beautiful hotel in a very central location, it was easy to walk everywhere. The staff were all super friendly and professional. We had an issue with our mattress and the front desk staff were very accommodating and we were able to switch rooms. They do have to address the issue with their mattresses though, as they are too soft and need to be replaced."
Zoe 5-night trip
Posted less than an hour ago
The Dagny Boston
The Royal Sonesta Boston

The Royal Sonesta Boston

10/10 Excellent
"Pool was closed and you still have to pay destination/ resort fee"
Drazen 4-night trip
Posted 1 hour ago
The Royal Sonesta Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"Very clean establishment Breakfast was limited"
Lyle 3-night trip
Posted 3 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

8/10 Good
"The room I had was a bit less then what I wold expect from a Westin propety. My room had one table with one chair. Scant."
Jerry 2-night trip
Posted 9 hours ago
The Westin Copley Place, Boston, a Marriott Hotel
Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Amazing location. Clean. Great brick wall vibe in hotel room. Classic boston"
Alice 1-night trip
Posted 12 hours ago
Harborside Inn Of Boston
Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Clean rooms, comfortable beds. It was a pleasant stay."
Jennifer 2-night trip
Posted 14 hours ago
Seaport Hotel Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

10/10 Excellent
"The staff was great. Getting the rewards for bonvoy is next to impossible. Still no reply to my email."
Jim 1-night trip
Posted 22 hours ago
The Westin Boston Seaport District

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, 1-minute walk from Massachusetts General Hospital. Offers complimentary wireless internet access, a seasonal outdoor pool, and a 24-hour fitness center. The Midtown Hotel MOD Collection by Sonesta: Hotel located near Encore Boston Harbor. Provides 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 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.

Explore a world of travel with Expedia