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Check availability on Winchester Family-Friendly Hotels

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Winchester Family-Friendly Hotels

Breakfast area
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

2.5 star property
Peterborough
  • Parking included
  • Free WiFi
  • Microwave
9.4 out of 10, Exceptional, (433)
Spacious rooms provide quiet comfort for families exploring nearby Greenfield State Park, just a 12-minute drive away. Modern perks include free WiFi, Hulu access for evening entertainment, microwaves for snacks, and ample outdoor seating overlooking the river.
The price is 3.303.534 ₫
3.870.131 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Riverhouse by Weekender (Formerly Jack Daniels Inn)
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
  • Indoor pool
8.6 out of 10, Excellent, (732)
The price is 3.183.310 ₫
3.501.641 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn & Suites Brattleboro I-91
Property grounds
The Putney Inn

The Putney Inn

2.5 star property
Putney
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
8.4 out of 10, Very good, (1005)
Spacious accommodation feature kid-friendly essentials like microwaves and refrigerators for convenient family meals. Just a 21-minute drive from North Shore Town Beach, this clean, quiet hotel offers free breakfast and well-lit parking for stress-free family escapes.
The Putney Inn
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
  • Cots/infant beds provided
  • Indoor pool
8.4 out of 10, Very good, (1006)
Splash-filled days await at this hotel's supervised indoor pool, where kids can play while parents unwind. Premium TV channels, pay films, and proximity to Cheshire Children's Museum create an ideal family retreat with comfortable rooms and a hearty breakfast buffet.
The price is 3.664.735 ₫
3.976.369 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Keene Hotel
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
Keene
  • Cots/infant beds provided
8.8 out of 10, Excellent, (754)
Young guests delight in nearby Cheshire Children's Museum while parents appreciate the complimentary breakfast buffet and comfortable accommodation. Spacious rooms feature sofa beds, blackout drapes, and premium TV channels for family film nights.
The price is 4.347.588 ₫
4.717.133 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Fairfield Inn & Suites by Marriott Keene Downtown
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
9.8 out of 10, Exceptional, (13)
Four Columns Inn
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
  • Business services
  • Housekeeping
9.6 out of 10, Exceptional, (628)
Spacious, immaculately clean rooms overlook serene river views, creating a peaceful family retreat. Children delight in cable TV entertainment while parents appreciate the refrigerator, laundry service, and proximity to Brattleboro Bowl, just 18 minutes away on foot.
The price is 4.011.435 ₫
4.352.407 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Riverside Hotel, an Ascend Collection Hotel
Reception
Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

2.5 star property
Brattleboro
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Room service
  • 24/7 front desk
6.0 out of 10, (736)
The price is 1.770.410 ₫
1.947.451 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Travelodge by Wyndham Brattleboro VT
Lunch and dinner served, American cuisine
Colonial Motel And Spa

Colonial Motel And Spa

3.0 star property
Brattleboro
  • 2 indoor pools
6.8 out of 10, (1005)
Splashing in dual indoor pools creates perfect family memories at this welcoming retreat. Children enjoy supervised swimming while parents indulge in the hot tub or sauna. Conveniently located near Brattleboro Bowl for additional entertainment, this motel provides comfortable rooms with refrigerators and microwaves.
The price is 3.163.800 ₫
3.480.182 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Colonial Motel And Spa
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.
View all properties

Top Winchester Hotel Reviews

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Great place. Historic—not for people who want fancy but clean with comfortable beds, very walkable to everything. Loved it!"
Heather 1-night trip
Posted 4 days ago
Latchis Hotel

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Frequently asked questions

What's Winchester like for family-friendly holidays?
The relaxing destination of Winchester is a great choice if you've been considering a holiday with the children. The boating, canoeing and kayaking spots are just a few things that make this an attractive holiday destination for families.
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 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Winchester are January, March, February and November, with each month seeing an average of 26 cm of snowfall.
What's there to see and do with your family in Winchester?
While you and your family are holidaying in Winchester, you may want to visit some family-friendly attractions such as Conant Public Library and Rhododendron State Park. Make sure that you have lots of time for activities such as Vermont Marketplace and The Stone Church.