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

Winchester Hotel Guide - Hotels with 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 Pool

Tonight
16 Aug - 17 Aug
Tomorrow
17 Aug - 18 Aug
Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug

Our top choices for Winchester hotels with a pool

Indoor pool
Standard Room, 2 Queen Beds, Non Smoking, Refrigerator
Free daily buffet breakfast
Lobby

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
includes taxes & fees
23 Aug - 24 Aug
Best Western Plus New Englander
Indoor pool
Premium bedding, down duvets, desk, blackout curtains
Bar (on property)
Premium bedding, down duvets, desk, blackout curtains

2. 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.
€130
includes taxes & fees
30 Aug - 31 Aug
Hyatt Place Boston/Medford
Indoor pool
Bar (on property)
Terrace/patio
Reception

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.
€126
includes taxes & fees
30 Aug - 31 Aug
Hilton Boston/Woburn
Indoor pool
Lobby
Bar (on property)
Bar (on property)

4. 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
includes taxes & fees
23 Aug - 24 Aug
Courtyard by Marriott Woburn/Boston North
Indoor pool
Ballroom
Exterior
Exterior

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.
€110
includes taxes & fees
7 Sept - 8 Sept
Crowne Plaza Boston - Woburn by IHG
Indoor pool
Terrace/patio
Lobby lounge
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.
€127
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Boston Woburn
Indoor pool
Terrace/patio
Reception
Exterior

7. Homewood Suites by Hilton Boston Woburn

Homewood Suites by Hilton Boston Woburn
Woburn
  • Dip into refreshing relaxation with an indoor pool, 24-hour fitness centre, and BBQ area.
€136
includes taxes & fees
23 Aug - 24 Aug
Homewood Suites by Hilton Boston Woburn
Terrace/patio
Bar (on property)
Lounge
Terrace/patio

8. 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.
€130
includes taxes & fees
28 Aug - 29 Aug
Boston Marriott Burlington
Seasonal outdoor pool
Lobby
Free daily continental breakfast
Lobby

9. 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.
€106
includes taxes & fees
23 Aug - 24 Aug
Fairfield Inn by Marriott Boston Woburn-Burlington
Seasonal outdoor pool
Exterior
Bar (on property)
Exterior

10. 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.
€134
includes taxes & fees
7 Sept - 8 Sept
HYATT house Boston/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

Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

10/10 Excellent
"Great stay for a Red Sox weekend! Awesome location, great people, clean room…lots of fantastic restaurants close by."
paul 2-night trip
Posted less than an hour ago
Copley Square Hotel, a FOUND Hotel
The Dagny Boston

The Dagny Boston

10/10 Excellent
"From the beautiful building to the welcoming staff to the great location, we thoroughly enjoyed our stay at The Dagny."
Aurora 1-night trip
Posted 2 hours ago
The Dagny Boston
Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"Beautiful hotel, excellent location within the Seaport district."
Michelle 1-night trip
Posted 7 hours ago
Seaport Hotel Boston
Doubletree By Hilton Boston Logan Airport Chelsea

Doubletree By Hilton Boston Logan Airport Chelsea

10/10 Excellent
"Room was well maintained & clean! Evelyn & Crabtree shampoo, conditioner & lotion— wish there was also body soap… Staff very nice & helpful; Great location ! Few steps from commuter train; Burger King & Dunkin Donut, etc"
ELIZABETH 3-night trip
Posted 14 hours ago
Doubletree By Hilton Boston Logan Airport Chelsea
Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Loved this cute boutique hotel. Location was fantastic and rooms were so nice! Loved the furnishings."
Renee 1-night trip
Posted 15 hours ago
Harborside Inn Of Boston

Frequently asked questions

What are some accommodation options 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 centre.
What is there to see and do in Winchester?
While you're in the area, consider exploring places such as TD Garden, Fenway Park and Encore Boston Harbor. Make a point to visit attractions such as 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 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.