Photo by Darrell Bumbala

Find Family Hotels in Jamaica, VT

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Jamaica Family Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Jamaica Family Hotels

Fridge, microwave, oven, stovetop
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods

Jamaica
9.0 out of 10, Wonderful, (6)
"Great location. House was recently updated but has some older charm in parts. Fun and cozy. Hot tub was great the first day but smell seemed off the next day. Perhaps more chlorine was needed. Great time , great trip. Pet friendly is a bonus and the house looks never used so the cleaning crew is doing great work. Will rent again next year perhaps !"
United States
Michael C.
The price is SAR 1,239
SAR 2,709 total
includes taxes & fees
8 Dec - 9 Dec
Family-friendly A-Frame near Stratton, Bromley & Magic — hot tub retreat in the quiet, peaceful woods
Interior detail
The White House Inn

The White House Inn

3.5 star property
Wilmington
9.2 out of 10, Wonderful, (260)
"The room was beautiful and the historic charm was wonderful "
United States
Karin
The price is SAR 622
SAR 684 total
includes taxes & fees
4 Jan - 5 January 2026
The White House Inn
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (737)
"Staff was friendly and pool was nice"
United States
Joshua
The price is SAR 432
SAR 475 total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn & Suites Brattleboro I-91
Children's activities
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (574)
"Nice old Inn!"
United States
Daniel
The price is SAR 615
SAR 886 total
includes taxes & fees
11 Dec - 12 Dec
The Equinox Golf Resort & Spa
Property grounds
The Putney Inn

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very Good, (1001)
"Nice motel. "
United States
Richard
The Putney Inn
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (13)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Exterior
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3.0 star property
Manchester Center
8.4 out of 10, Very Good, (861)
"Room was fantastic, had a lovely stay."
United States
Cody
The price is SAR 402
SAR 504 total
includes taxes & fees
14 Dec - 15 Dec
The Palmer House Resort, an Ascend Collection Hotel
Arcade
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (938)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
The price is SAR 653
SAR 790 total
includes taxes & fees
7 Jan - 8 January 2026
The Black Bear Lodge at Stratton Mountain Resort
Sundeck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (628)
"Clean room, beautiful location"
United States
Marcie
The price is SAR 571
SAR 620 total
includes taxes & fees
5 Jan - 6 January 2026
Riverside Hotel, an Ascend Collection Hotel
Outdoor dining
Stanford House

Stanford House

2.5 star property
Manchester Center
9.0 out of 10, Wonderful, (66)
"This was a great comfortable place to stay with outstanding views."
United States
David
The price is SAR 357
SAR 429 total
includes taxes & fees
8 Dec - 9 Dec
Stanford House
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 Jamaica Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 22 hours ago
Pointe at Castle Hill Resort

Explore a world of travel with Expedia

Frequently asked questions

What's Jamaica like for family-friendly vacations?
The destination of Jamaica is a great choice if you've been thinking about a vacation with your kids. The horseback riding, sledding, and parks are just a few things that make this an attractive vacation spot for families. Fly into Springfield, VT (VSF-Hartness State), which is located 21.1 mi (34 km) from the city center.
When's the best time to book a family-friendly vacation in Jamaica?
The hottest months are usually July and August with an average temp of 64°F, while the coldest months are January and February with an average of 24°F. The snowiest months in Jamaica are January, March, November, and February, with each month seeing an average of 9 inches of snowfall.
What's there to see and do with your family in Jamaica?
Jamaica State Park, Hot Glass Works, and Margie's Muse Handweaving & Gallery are interesting attractions you and your family will enjoy exploring while you are staying in Jamaica. Make sure you have plenty of time to take in activities in the area like Stratton Mountain Resort and Mount Snow.