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$190

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Check availability on Winchester Family Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Winchester family-friendly hotels

A modern restaurant with a central counter, multiple dining tables, and chairs.
A hotel room with a desk, two beds, a TV, a lamp, and a painting on the wall.
An indoor swimming pool with a tiled ceiling, lounge chairs, and a view of the outdoors.
A modern hotel lobby with a seating area featuring blue upholstered sofas, a coffee table with a vase of flowers, and a large flat-screen TV mounted on a dark wall.

1. Best Western Plus New Englander

Best Western Plus New Englander
Woburn
AU$220
includes taxes & fees
27 Sept - 28 Sept
Best Western Plus New Englander
A modern dining area with tables and chairs, a kitchen counter, and a sign that reads "Delight in the day".
A hotel room with a desk, chair, bed, and a sofa.
A reception area with a wooden reception desk, a green rug, and two orange chairs.
A modern bathroom with a bathtub, a shower, a sink, and a mirror.

2. Spark by Hilton Woburn Boston

Spark by Hilton Woburn Boston
Woburn
AU$244
includes taxes & fees
27 Sept - 28 Sept
Spark by Hilton Woburn Boston
A hotel lobby with a staircase, seating area, and patterned carpet.
A modern bar area with a flat-screen TV, bar stools, and a variety of bottles on shelves.
A modern bar area with a large TV, a fireplace, and a patterned carpet.
A hotel lobby with a patterned carpet, seating area with armchairs and sofas, a staircase, and a cityscape painting on the wall.

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$270
includes taxes & fees
4 Oct - 5 Oct
Courtyard by Marriott Woburn/Boston North
A modern lounge area with a glass wall, a central fire feature, and seating arrangements.
An outdoor seating area with modern furniture and a fire feature.
A modern hotel with a swimming pool, multiple balconies, and a glass facade.
A modern bar area with a long counter, multiple bar stools, and a variety of bottles and glasses on shelves.

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$259
includes taxes & fees
4 Oct - 5 Oct
Hilton Boston/Woburn
A restaurant area with a counter, stools, a refrigerated display case with beverages, and menu boards.
A modern hotel building with a white facade, multiple floors, and a central entrance.
A swimming pool with clear blue water, surrounded by lounge chairs and a large window.

5. 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$340
includes taxes & fees
4 Oct - 5 Oct
Hyatt Place Boston/Medford
A modern hotel with a covered entrance, multiple floors, and a landscaped area in front.
A modern hotel room with a sectional sofa, armchairs, a flat-screen TV, and large windows with curtains.
A modern kitchen with a bar area, bar stools, pendant lighting, and a large TV.
A modern building with large windows, outdoor seating, and a well-maintained garden.

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$238
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn Boston Woburn
A hotel entrance with a glass door, illuminated pillars, and a paved walkway.
A modern bathroom with a glass-enclosed shower, a toilet, a sink, and a large mirror.
A living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a kitchen area visible in the background.
A buffet area with various food options, including fruits, vegetables, and prepared dishes.

7. Crowne Plaza Boston - Woburn by IHG

Crowne Plaza Boston - Woburn by IHG
Woburn
AU$265
includes taxes & fees
4 Oct - 5 Oct
Crowne Plaza Boston - Woburn by IHG
A spacious kitchen with a long counter, bar stools, and modern pendant lighting.
A bathroom with a bathtub, toilet, and sink.
A modern hotel with a prominent 'HYATT house' sign, a covered entrance, and well-maintained landscaping.
An outdoor patio area with a stone fire pit, wicker furniture, and a pergola.

8. HYATT house Boston/Burlington

HYATT house Boston/Burlington
Burlington
  • Family-friendly fun with seasonal outdoor pool and free breakfast near Burlington Ice Palace.
AU$268
includes taxes & fees
4 Oct - 5 Oct
HYATT house Boston/Burlington
An outdoor patio area with a sofa set, a dining table, and a large umbrella.
A modern bar area with a long counter, multiple stools, and a variety of bottles and glasses.
A modern reception area with a curved desk, seating, and a large mirror wall.

9. 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$275
includes taxes & fees
27 Sept - 28 Sept
Boston Marriott Burlington
A hotel room with a large bed, a desk, a chair, a television, and a wardrobe.
A hotel lobby with a reception desk, a Red Roof Plus sign, and a bench.
A hallway with a vending machine and a Coca-Cola refrigerator.
A compact kitchen with a refrigerator, a coffee machine, and a washing machine.

10. Red Roof Inn PLUS+ Boston - Woburn/ Burlington

Red Roof Inn PLUS+ Boston - Woburn/ Burlington
Woburn
  • Rooms equipped with cosy sofa beds, cots, and premium TV channels offer the perfect family retreat near Woburn Bowladrome.
AU$190
includes taxes & fees
29 Sept - 30 Sept
Red Roof Inn PLUS+ Boston - Woburn/ Burlington
View all properties

Choose what matters most at family-friendly hotels in Winchester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Winchester Hotel Reviews

The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

8/10 Good
"a little pricey for what it is, but great location, easy parking, room was clean and quiet"
Daniel 1-night trip
Posted 1 hour ago
The Midtown Hotel MOD Collection by Sonesta
The Godfrey Hotel Boston

The Godfrey Hotel Boston

10/10 Excellent
"Great walkable location, close to the Freedom Trail, restaurants and shops."
Thomas H 2-night trip
Posted 1 hour ago
The Godfrey Hotel Boston
Hilton Boston Park Plaza

Hilton Boston Park Plaza

8/10 Good
"Rooms are on small side but overall great location and friendly staff."
Lesley 1-night trip
Posted 1 hour ago
Hilton Boston Park Plaza
The Dagny Boston

The Dagny Boston

10/10 Excellent
"We had a great stay at the Dagny, it is a beautiful hotel!"
Ashley 1-night trip
Posted 2 hours ago
The Dagny Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

10/10 Excellent
"Great place. Highly recommended!"
Steven 4-night trip
Posted 15 hours ago
Hyatt Regency Boston/Cambridge
Hyatt Regency Boston Harbor

Hyatt Regency Boston Harbor

10/10 Excellent
"My husband and I loved our stay!!! Our room view was awesome every night and morning! You could also sit outside by the harbor and enjoy a walk with the stunning view! My husband called ahead for our anniversary and they did this beautiful presentation on the bed! The bed was comfortable, loved the bathroom lighting. The clam chowder was so lovely. The closeness to the airport was a plus with the shuttle and you didn’t hear any airplane noise inside. We used the shuttle for the train station as well and all of our shuttle drivers were a delight. A special shoutout to CHAD!!!! Chad is the man!! Hotel provided water as well."
Glory 3-night trip
Posted 23 hours ago
Hyatt Regency Boston Harbor
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

10/10 Excellent
"VANESSA THE FRONT DESK WAS VERY GOOD!"
Jaime 1-night trip
Posted 1 day ago
Hilton Garden Inn Tewksbury Andover
The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent
"."
Markisha 3-night trip
Posted 3 days ago
The Westin Copley Place, Boston, a Marriott Hotel

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, football matches and wildlife 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?
Winter Pond and Griffin Photography Museum 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 Fenway Park, Encore Boston Harbor and Harvard Square.
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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