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

Family Hotels & Resorts in Winchester from AU$174

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Check availability on Winchester Family Hotels

Tonight
9 Aug - 10 Aug
Tomorrow
10 Aug - 11 Aug
Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug

Our top choices for Winchester family-friendly hotels

1. Best Western Plus New Englander

Best Western Plus New Englander
Woburn
AU$187
includes taxes & fees
13 Aug - 14 Aug
Best Western Plus New Englander

2. Hyatt Place Boston/Medford

Hyatt Place Boston/Medford
Medford
  • Family holidays bloom at this Boston escape with spacious rooms, an indoor pool, and 24/7 amenities for all ages.
AU$202
includes taxes & fees
16 Aug - 17 Aug
Hyatt Place Boston/Medford

3. Courtyard by Marriott Woburn/Boston North

Courtyard by Marriott Woburn/Boston North
Woburn
  • Splash into family-friendly adventures with an indoor pool, premium entertainment, and nearby attractions for all ages to enjoy together.
AU$200
includes taxes & fees
16 Aug - 17 Aug
Courtyard by Marriott Woburn/Boston North

4. Hilton Boston/Woburn

Hilton Boston/Woburn
Woburn
  • Family holiday perfection at Hilton Boston/Woburn with indoor pool and convenient access to local attractions.
AU$206
includes taxes & fees
16 Aug - 17 Aug
Hilton Boston/Woburn

5. Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
Woburn
AU$174
includes taxes & fees
7 Sept - 8 Sept
Crowne Plaza Boston - Woburn by IHG

6. Hampton Inn Boston Woburn

Hampton Inn Boston Woburn
Woburn
  • Explore this welcoming family haven where kids splash in the heated indoor pool and enjoy free perks while parents relax in comfort.
AU$206
includes taxes & fees
23 Aug - 24 Aug
Hampton Inn Boston Woburn

7. HYATT house Boston/Burlington

HYATT house Boston/Burlington
Burlington
  • Family-friendly fun with seasonal outdoor pool and free breakfast near Burlington Ice Palace.
AU$228
includes taxes & fees
22 Aug - 23 Aug
HYATT house Boston/Burlington

8. Boston Marriott Burlington

Boston Marriott Burlington
Burlington Town Center
  • Splash into family adventures with indoor and outdoor pools, free parking, and Netflix for kids at this hotel near Boston.
AU$213
includes taxes & fees
21 Aug - 22 Aug
Boston Marriott Burlington

9. Homewood Suites by Hilton Boston Woburn

Homewood Suites by Hilton Boston Woburn
Woburn
AU$207
includes taxes & fees
16 Aug - 17 Aug
Homewood Suites by Hilton Boston Woburn

10. Residence Inn by Marriott Boston Woburn

Residence Inn by Marriott Boston Woburn
Woburn
AU$240
includes taxes & fees
23 Aug - 24 Aug
Residence Inn by Marriott Boston Woburn
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Choose what matters most at family-friendly hotels in Winchester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Winchester Hotel Reviews

Seaport Hotel Boston

Seaport Hotel Boston

10/10 Excellent
"The hotel was located in a great area for walking to many restaurants and sites. Ver comfortable and friendly staff"
Steve 1-night trip
Posted less than an hour ago
Seaport Hotel Boston
The Westin Boston Seaport District

The Westin Boston Seaport District

10/10 Excellent
"Staff was amazing. Rooms were clean."
Jeffrey 3-night trip
Posted 2 hours ago
The Westin Boston Seaport District
Hilton Boston Park Plaza

Hilton Boston Park Plaza

10/10 Excellent
"Beautiful hotel in the heart of Boston."
Nathaniel 1-night trip
Posted 2 hours ago
Hilton Boston Park Plaza
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

8/10 Good
"The hotel is centrally located, the staff was amazing the waiting room downstairs was fabulous and the adjoining bar was a bonus. The only drawback for me was room size, but we did not spend alot of time in the room, so it was tolerable."
Corey 1-night trip
Posted 2 hours ago
Club Quarters Hotel Faneuil Hall, Boston
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent
"The hotel was very clean and the staff was very helpful. I highly recommend it!!"
Melissa 1-night trip
Posted 3 hours ago
The Midtown Hotel MOD Collection by Sonesta
Copley Square Hotel, a FOUND Hotel

Copley Square Hotel, a FOUND Hotel

8/10 Good
"Met our needs small room but we spent our time out and about. Sox game and Duck boat. Nice bar to finish off day"
Stephen 2-night trip
Posted 4 hours ago
Copley Square Hotel, a FOUND Hotel
Wyndham Boston Beacon Hill

Wyndham Boston Beacon Hill

10/10 Excellent
"Check-in process was wonderful. Props to the front desk. 🙏"
Andres G 1-night trip
Posted 6 hours ago
Wyndham Boston Beacon Hill
Harborside Inn Of Boston

Harborside Inn Of Boston

10/10 Excellent
"Amazing location & clean and comfortable."
Kylie 2-night trip
Posted 8 hours ago
Harborside Inn Of Boston
The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"The staff is all very helpful and friendly. The property is very clean. The beds are nice. Free water and snacks in the room. Good location."
MELINDA 1-night trip
Posted 8 hours ago
The Godfrey Hotel Boston

Frequently asked questions

What's Winchester like for family-friendly holidays?
The destination of Winchester is a good option if you've been considering a getaway with the children. The lake views, wildlife and football matches are just a few things that make this an attractive holiday destination for families. Fly into Bedford, MA (BED-Laurence G. Hanscom Field), which is the closest airport, or Boston, MA (BNH-Boston Harbor Seaplane Base), which is located 8.4 mi (13.5 km) from the city centre.
When's the best time to book a family-friendly holiday in Winchester?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Winchester are January, February, March and April, with each month seeing an average of 13 cm of snowfall.
What's there to see and do with your family in Winchester?
Griffin Photography Museum and Winter Pond are interesting attractions that you and your family may enjoy exploring while you are staying in Winchester. Make sure that you have plenty of time to take in activities in the area such as TD Garden, Fenway Park and Encore Boston Harbor.
What's the best way for us to get around Winchester?
To explore the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station. Winchester may not have many public transport choices, so consider renting a car to explore more.

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