Photo by mike dobias

Find hotels in Windsor, VT from 2.115.990 ₫

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 prices for these dates

Tonight
20 Dec - 21 Dec
Tomorrow
21 Dec - 22 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Windsor hotels

Exterior
Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (12)
"An absolutely stunning property! The cabin was clean, well stocked and perfectly located to see the gorgeous sunrise. So very grateful for our quick trip at Fat Sheep Farm. Looking forward to returning! "
United States
Jasmine
Fat Sheep Farm & Cabins
Restaurant
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
Victorian charm awaits at this quiet Woodstock B&B where travellers rave about the delicious morning meal. Relax in the garden, enjoy evening drinks at the bar, or explore nearby Union Arena and Five Elm Arches from this peaceful retreat.
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Exterior
Kedron Valley Inn

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (329)
Located in South Woodstock, this inn features the Ransom Tavern for dinner and a cosy bar/lounge with terrace. Free WiFi and parking add convenience while Union Arena and VINS Nature Centre provide nearby exploration options.
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
The price is 5.791.280 ₫
6.370.408 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Kedron Valley Inn
Hallway
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
Discover a tranquil retreat near the train station in Woodstock featuring an indoor pool, hot tub, and on-site 506 Bistro and Lounge. Guests love the helpful staff, complimentary breakfast, and convenient access to Union Arena Community Centre.
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is 5.078.795 ₫
6.551.646 ₫ total
includes taxes & fees
21 Dec - 22 Dec
On The River Inn
Comfort Townhome | In-room dining
Brook Road Condo

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is 4.841.960 ₫
7.880.290 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Brook Road Condo
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
This cosy Woodstock B&B offers free continental breakfast daily, plus convenient WiFi and parking. Explore nearby attractions like Billings Park and Trail or Red Wagon Toy Company, then return to this welcoming retreat.
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is 6.552.435 ₫
7.207.678 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Stay At Jimmy's
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (181)
Surrounded by mountain splendour, this family-friendly retreat offers Kent Bistro dining and relaxing amenities including a sauna. Just minutes from Killington Resort and Pico Mountain skiing, guests consistently praise the attentive staff.
"All round fantastic place to stay "
United Kingdom
Stephen
The price is 5.760.354 ₫
6.994.264 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Meadows Lodge
Standard Room, 2 Double Beds | Desk, blackout curtains, iron/ironing board, free WiFi
Royal Inn Claremont

Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.6 out of 10, (318)
Located in Claremont, this welcoming motel offers convenient amenities including complimentary WiFi and self parking. Nearby hiking trails and kayaking spots provide outdoor adventure, while Tremont Square and Claremont Opera House are just minutes away.
"Affordable"
United States
Cheryl
The price is 2.894.650 ₫
3.140.695 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Royal Inn Claremont
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
This charming B&B offers free WiFi and parking with a daily buffet breakfast. Outdoor enthusiasts will love the nearby hiking trails and mountain biking, while popular attractions like Bonnie's Bundles Dolls are just minutes away.
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is 5.496.703 ₫
5.991.407 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Stone Hearth Inn and Eatery
Front of property – evening/night
Main and Mountain Bar & Motel

Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (211)
Discover Vermont's beauty at this Ludlow motel offering free WiFi, parking, and an area shuttle to nearby Okemo Mountain Resort. After outdoor fun, unwind at the on-site bar before retiring to comfortable accommodation. Dorsey Park is also located close by.
"The bar was wonderful! Clean and great guest services"
United States
Mariah
The price is 8.099.757 ₫
8.909.733 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Main and Mountain Bar & Motel
Interior
The Inn at Weathersfield

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
This inviting Perkinsville inn offers free Wi-Fi, breakfast and parking. Unwind with drinks at the bar/lounge or savour a meal at the restaurant. North Springfield Lake and Stoughton Pond Recreation Areas await nearby.
"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
The Inn at Weathersfield
Lobby sitting area
The Hartness House

The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (328)
Beautifully situated with easy access to transport, this charming hotel offers free WiFi and parking. Outdoor enthusiasts will appreciate nearby hiking trails, kayaking, and mountain biking opportunities, with Muckross State Park just a short drive away.
"nice folks, practical place to stay. "
United States
Mark
The price is 4.633.024 ₫
5.096.326 ₫ total
includes taxes & fees
21 Dec - 22 Dec
The Hartness House
Exterior
Best Western Springfield Hotel

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (806)
Tucked away in Springfield, this tranquil hotel offers a refreshing indoor swimming experience and fitness centre. Guests can explore nearby Baltimore Covered Bridge while enjoying free breakfast, WiFi, and parking throughout their stay.
"so clean and friendly it was a perfect stay!"
United States
Colette
The price is 4.002.775 ₫
4.403.053 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Springfield Hotel
Interior
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm
3.0 star property
Quechee
9.0 out of 10, Wonderful, (1000)
Set along Wilderness Trails in scenic Quechee, this historic inn offers complimentary gourmet breakfast and convenient access to Vermont Institute of Natural Science. Enjoy dining at the acclaimed restaurant, unwind in the garden, or sip drinks at the welcoming bar.
"Beautiful historic property. We had dinner at the hotel restaurant and it was fantastic!"
United States
Dion
The price is 4.002.511 ₫
4.402.762 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
The Quechee Inn at Marshland Farm
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9)
Tucked in charming Goshen, this welcoming cottage offers a private garden and fully equipped kitchen for your rural escape. Explore nearby Olive G. Pettis Library and Gunnison Lake, then return to relax with Smart TV entertainment.
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin
Interior
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
Surrounded by seasonal adventure, this charming 3-star B&B offers complimentary continental breakfast, WiFi, and parking. Winter enthusiasts will love the cross-country skiing and snowboarding options, with Billings Park and Dana House Museum just minutes away.
"Charming bed and breakfast"
United States
Nicholas
The price is 4.440.656 ₫
4.884.853 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Vesper
Interior entrance
The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (370)
Set along the Connecticut River, this welcoming retreat offers complimentary breakfast and parking. Unwind at the bar after exploring nearby attractions, or relax in the hot tub. Clean rooms include refrigerators and microwaves for added convenience.
"Great place to stay! "
United States
Candace M
The price is 3.292.007 ₫
3.571.735 ₫ total
includes taxes & fees
30 Dec - 31 Dec
The Common Man Inn & Restaurant
Exterior
Killington Grand Hotel

Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
8.8 out of 10, Excellent, (193)
This ski-in/ski-out hotel sits at the base of Killington Resort, offering direct mountain access. Unwind in 2 hot tubs or the outdoor pool after hitting the slopes. The full-service spa provides rejuvenating deep-tissue massages, while the restaurant and bar complete your alpine retreat.
"Fantastic....Perfect place for a fall getaway."
United States
Justin
Killington Grand Hotel
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
Enjoy a peaceful retreat near Killington and Sugarbush ski resorts. This well-maintained motel offers clean rooms and friendly staff in a beautiful Vermont setting. Free WiFi and parking make it easy to explore Ottaquechee River and local hiking trails.
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is 2.178.882 ₫
4.041.458 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel
Deluxe Double Room | Free WiFi
Newport Motel

Newport Motel

Newport Motel
2.0 star property
Newport
8.8 out of 10, Excellent, (267)
Just 36 minutes from Lebanon Municipal Airport, this clean motel offers complimentary WiFi and parking. Close to Wendell Marsh Wildlife Management Area and Newport Historical Society for local exploration.
"Nice place to short stay "
Mexico
Vanessa
The price is 2.770.969 ₫
3.006.502 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Newport Motel
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Windsor attractions

Bowers Covered Bridge - Vermont

Brownsville Trail

This challenging 5.2-mile trail rewards hikers with panoramic views and the historic Norcross Quarry from the early 1900s. Pack water and wear sturdy boots for the 2,395-foot ascent through Vermont's forests.
See properties
La rivière Otter Creek pour aller à Vergennes, Vermont.

Paradise Park

Paradise Park offers diverse ecosystems around Lake Runnemede, with well-maintained trails through forests and meadows. Observe abundant wildlife including birds, turtles, and beavers in this peaceful natural sanctuary.
See properties

Learn more about Windsor

Step back in time at the American Precision Museum, where industrial history comes alive through fascinating exhibits. Afterwards, savour craft brews at Harpoon Brewery or hike the scenic trails of Mt Ascutney State Park for breathtaking views.

See all hotels in Windsor
Cornish Windsor Covered Bridge

Top Windsor Hotel Reviews

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

10/10 Excellent
"The people who work there are great! Very attentive. The location is very accessible and a rocks throw from the entrance to MT Sunapee Ski Area."
Kevin 1-night trip
Posted 7 days ago
Hideaway Inn Mt.Sunapee

More cheap stays in Windsor

Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

442 North Hartland Rd White River Junction VT
The price is 1.923.627 ₫ per night from 3 Jan to 4 Jan
1.923.627 ₫
2.115.990 ₫ total
3 Jan - 4 Jan 2026
includes taxes & fees
6.2/10 (1,000 reviews)

Hotels in Windsor with star rating

Frequently asked questions

What's the weather like in Windsor?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -6°C. The snowiest months in Windsor are March, January, November and February, with each month seeing an average of 38 cm of snowfall.