The Best Family Hotels in Windsor, VT from NT$5,219 in 2026

A snow-covered river valley with a bridge and a town.

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Our top choices for Windsor family-friendly hotels

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

NT$4,306

NT$5,220 total

includes taxes & fees

Sep 20 - Sep 21

Standard Room, 2 Double Beds, Accessible, Non Smoking | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels

Desk, iron/ironing board, cribs (free), WiFi (free)

2. Best Western West Lebanon-Hanover Hotel

West Lebanon

Family vacations made special with an outdoor pool, kids' play spaces, and nearby aquatic center adventures await.

NT$5,802

NT$6,295 total

includes taxes & fees

Oct 18 - Oct 19

Combined shower/tub, eco-friendly toiletries, hair dryer, towels

3. Align Inn Vermont

Quechee

Family-friendly Vermont retreat makes a splash with indoor pool steps from Quechee State Park for all-weather fun.

NT$7,013

NT$7,715 total

includes taxes & fees

Sep 20 - Sep 21

4. Hotel Coolidge

White River Junction

Historic hotel offers family adventures with child-friendly amenities and nostalgic charm near water activities.

NT$4,744

NT$5,219 total

includes taxes & fees

Sep 20 - Sep 21

Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer

Desk, blackout drapes, iron/ironing board, WiFi (free)

Deluxe Suite | Desk, blackout drapes, iron/ironing board, WiFi (free)

5. Sleep Woodstock Motel

Woodstock

Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.

NT$4,334

NT$5,996 total

includes taxes & fees

Sep 24 - Sep 25

6. Comfort Inn White River Junction

White River Junction

Family-friendly adventure near Dartmouth College with a fitness center, premium TV, and complimentary breakfast each morning.

NT$5,024

NT$5,526 total

includes taxes & fees

Oct 19 - Oct 20

Mansion Suite (Room 12) | Bathroom | Free toiletries, hair dryer, towels

Mansion Suite (Room 2) | Living area | 32-inch flat-screen TV with digital channels, TV, streaming services

7. The Hartness House

Springfield

NT$5,637

NT$6,200 total

includes taxes & fees

Sep 21 - Sep 22

8. Hilton Garden Inn Hanover Lebanon

Lebanon

NT$5,999

NT$6,508 total

includes taxes & fees

Sep 20 - Sep 21

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Choose what matters most at family-friendly hotels in Windsor

Breakfast included

Pool

All-inclusive

4 stars

5 stars

Top Windsor Hotel Reviews

Mountain Meadows Lodge

8/10 Good

"The property is very comfortable with beautiful view of the lake. The evening bon fire proved to be a way to meet fellow travelers. There are many public rooms to keep you engaged. Site manager is very helpful and friendly."

Woodstock Inn & Resort

8/10 Good

"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."

Hotel Coolidge

8/10 Good

"This is a very old hotel on the national historic record. Because of that the doors and floors creak and the floors slope. The bathroom has older fixtures but work fine. Our room was actually two rooms; one with a queen bed and one with a small couch and sink. Both rooms had TVs. We had a small fridge. Bed was comfortable. They had an elevator that was very slow but since we had heavy items we were very grateful for it. The stairway and moldings were beautiful. If you enjoy historic architecture you will appreciate this hotel. The parking seemed a bit sketchy but was actually fine. They had a fireplace and a Keurig in lobby so tea, coffee and hot chocolate available 24/7. Also had vouchers for discounts at neighboring breakfast sites. They are dog friendly, but only for specified rooms. They also had a refundable $100 charge for any damage done due to the dog. There was a $25 charge for the dog which is pretty standard. All in all it was a fine place to stay."

On The River Inn

8/10 Good

"Housekeeping was a bit lax. No tissues and only one hand towel. The rest of the Inn was great!"

The Mountain Inn at Killington

10/10 Excellent

"Stay was great, they have bike lockers to keep bikes at night super close to Killington lifts"

Pointe at Castle Hill Resort

10/10 Excellent

"I loved that they have 2 room suites with a full kitchen. Everyone who worked there was beyond efficient and friendly. The fact that its dog friendly was great as I had been on the road almost 3 weeks and was missing my pups ."

The Shire Woodstock

10/10 Excellent

"Na"

White River Inn and Suites

8/10 Good

"Keith helped us at the front desk and we had such a good experience bc of his help with some booking issues we had."

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good

"Stayed here because of the hot tub!!! Love that it was open until 11pm but wished it was open by like 8 am so we could have used it before we started our day !!"

Frequently asked questions

What's Windsor like for family-friendly vacations?

The destination of Windsor is a good option if you've been considering a getaway with the kids. The sledding, golfing, and forests are just a few things that make this an attractive family vacation spot. Arrange a flight into Lebanon, NH (LEB-Lebanon Municipal), which is located 10.7 mi (17.3 km) from the city center.

When's the best time to book a family-friendly vacation in Windsor?

The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.

What's there to see and do with your family in Windsor?

While you and your family are staying in Windsor, you might want to visit some family-friendly attractions such as Brownsville Trail, Windsor Public Library, and Weathersfield Proctor Library. Make sure you have lots of time for activities like Claremont Opera House and Maple Lanes.

What's the best way for us to get around Windsor?

To see more of the larger area, hop aboard a train at Windsor Station. Windsor might not have very many public transportation choices so consider a car rental to maximize your time.

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Change your mind

Treat yourself

Be picky

Check availability on Windsor Family Hotels

Our top choices for Windsor family-friendly hotels

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG