Family Hotels & Resorts in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester Family Hotels

Best Winchester Family Hotels

Nantasket Beach Resort
Exterior

Nantasket Beach Resort

3.0 star property
8.4 out of 10, Very good, (1019)
"Such a small island feel. Very nice hotel. Perfect location. Pool is great. Everyone is so nice. We will return. "
Kesha
The price is AU$371
includes taxes & fees
30 July - 31 July
Nantasket Beach Resort
Salem Waterfront Hotel & Suites
Indoor pool

Salem Waterfront Hotel & Suites

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Very nice. Clean and great location. We were in town for a wedding and rented a large king suite. We had a large living area that was a great space to visit with
family
. "
Jennifer
The price is AU$461
includes taxes & fees
30 July - 31 July
Salem Waterfront Hotel & Suites
Hawthorne Hotel
2 restaurants, breakfast, lunch, dinner served; American cuisine

Hawthorne Hotel

3.5 star property
9.4 out of 10, Exceptional, (1301)
"Beautiful hotel. Very
kid-friendly
, our
kids
found it very fancy, but very friendly. The staff was so nice. All the food was really good (simple and well-prepared enough for picky eaters) and well-priced, I thought. The location was the best aspect, right across the way from the Salem Witch Museum and also the big park as well as all the shops; very picturesque. We don’t usually spring for a pricier hotel, but this was worthwhile! "
Rosemary
Hawthorne Hotel
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
Apartment (0 Bedroom) | Interior

1 Mi to Downtown Salem: Studio w/ Fire Pit Access

3.0 star property
9.0 out of 10, Wonderful, (2)
"Very nice place to stay. Super cute and clean. So many extras. Unfortunately not ideal for my tall husband. The shower was a bit small for his size but just right for me. The roses in the yard smelled great. Thanks for a great stay. "
Rebecca
The price is AU$461
includes taxes & fees
5 Aug - 6 Aug
1 Mi to Downtown Salem: Studio w/ Fire Pit Access
1 Mi to Downtown: Salem Vacation Rental!
Apartment (1 Bedroom) | Interior

1 Mi to Downtown: Salem Vacation Rental!

3.0 star property
The price is AU$468
includes taxes & fees
30 July - 31 July
1 Mi to Downtown: Salem Vacation Rental!
The Bell Inn
Honeymoon Room | In-room dining

The Bell Inn

5.0 star property
9.4 out of 10, Exceptional, (170)
"Wonderful staff. Really neat accommodations. They make you feel like
family
. "
Craig
The Bell Inn
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
3 bedrooms, in-room safe, desk, travel cot

37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse

9.0 out of 10, Wonderful, (31)
"This was a great home away from home that accomodated my entire
family
. The host was friendly and responsive, and the property was clean and had all the essentials for a great stay. We will definitely rent this property again when we visit Boston!"
Candice M.
The price is AU$741
includes taxes & fees
11 Aug - 12 Aug
37-SPRING GETAWAY EARLY BIRD 10%! Greater Boston Cozy Townhouse
Howard Johnson by Wyndham Quincy/Boston
BBQ/picnic area

Howard Johnson by Wyndham Quincy/Boston

2.0 star property
7.8 out of 10, Good, (1015)
"The hotel was decent, needs minor repairs. Light breakfast was a treat. Showers were the best, strong pressure. Love the diversity of pillows. Disappointed the front desk could not give change for the vending machines."
Laura
The price is AU$210
includes taxes & fees
17 Aug - 18 Aug
Howard Johnson by Wyndham Quincy/Boston
Hyatt Place Boston/Braintree
Reception

Hyatt Place Boston/Braintree

3.5 star property
9.0 out of 10, Wonderful, (2444)
"Excellent hotel to stay in surrounded by restaurants and shopping mall. "
John
The price is AU$225
includes taxes & fees
17 Aug - 18 Aug
Hyatt Place Boston/Braintree
Comfort Inn Randolph - Boston
Free daily buffet breakfast

Comfort Inn Randolph - Boston

2.5 star property
7.8 out of 10, Good, (1027)
"Good location and it was great that breakfast was included."
Maly
The price is AU$206
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn Randolph - Boston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Winchester Hotel Reviews

Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"We love staying here when we travel to Ireland as it’s a great place to stay overnight with plenty to do. Every time we stay, we find something new that we haven’t yet experienced. We are originslly from this area but moved to North Carolina so this is a great welcome home and we enjoy our stay every time we are here. "
Karen 1-night trip
Posted 2 days ago
Hyatt Regency Boston Harbor

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 sporting events 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?
Middlesex Fells Reservation 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 New England Aquarium.
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.