1975+ Hotel & Resort Deals in Windsor County |
  1. USA
  2. Vermont
  3. Windsor County

Windsor County Hotels, Resorts, and Rentals

About Windsor County Vacation Rentals

There are more than 1975 places to stay in Windsor County that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Windsor County.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Windsor County, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Windsor County. Places to stay near Windsor County are 1127.66 ft² on average, with prices averaging US $537 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Windsor County with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

Show more
Show less

Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Windsor County

Type Count
Vacation Homes 985
Holiday Apartments 197
Cabin Rentals 104
Ski Chalet Rentals 55
Others 37
Cottages 36
B&B 26
Villas 5
Unique Vacation Rentals 4

Use these Quick Filters to Find a Vacation Rental in Windsor County

★ Pro Tip: Hotala has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Windsor County.

Weather in Windsor County, VT

View the weather forecast for Windsor County before booking your Windsor County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Windsor County's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of Windsor County's top attractions, neighborhoods, and points of interest.


Okemo Mountain Resort
Quechee Gorge
Jackson Gore Ski Resort at Okemo
King Arthur Flour
Quechee Gorge Village
Little Pico Mountain
Weston Playhouse
Suicide Six Ski Area
Weston Priory
Mt Ascutney State Park
Upper Valley Aquatic Center
Sugarbush Farm
Simon Pearce Mill
Mount Ascutney
Woodstock Country Club
Billings Farm and Museum
Okemo Valley Golf Club
Silver Lake State Park
Vermont River Tubing
Woodstock Town Hall Theatre
Briggs Opera House
Montshire Museum of Science
Wilderness Trails
Buttermilk Falls
Long Trail Brewing Company
Calvin Coolidge Historic Site
Mount Tom Peak
Vermont Institiute of Natural Science
Calvin Coolidge Homestead
Harpoon Brewery

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Ludlow 675 Properties
Bridgewater Corners 113 Properties
West Bridgewater 91 Properties
Cavendish 82 Properties
Woodstock 81 Properties
Quechee 72 Properties
Chester 60 Properties
Chester Depot 60 Properties
Plymouth 56 Properties
Proctorsville 45 Properties
Weston 35 Properties
Andover 29 Properties

Complexes around Windsor County, VT


Cedarbrook 29 Properties
Winterplace Ludlow 22 Properties
Located 20 Properties
Okemo Mountain Lodge 13 Properties
Efficiency Sofa 8 Properties
Kettle Brook 8 Properties
Hotel 6 Properties
Br Of Ski Lift 4 Properties
Ghia Farm Road 4 Properties
Comfort Inn White River Junction 3 Properties
Hampton Inn White River Junction 3 Properties
Holiday Inn Club Vacations Mount Ascutney Resort Ihg Hotel 3 Properties
Holiday Inn Express Hotel White River Junction Ihg 3 Properties
Hotel Coolidge 3 Properties
Mountain Lodge At Renovated 3 Properties
See More Complexes

Frequently Asked Questions About Windsor County?

What are the top hotels or resorts in Windsor County?

You have a lot of choices in or near Windsor County. If you need a hotel in the Windsor County area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Windsor County:

How many vacation rentals have private pools in Windsor County?

There are 59 accommodation options with private pools in or near Windsor County. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

Which hotel or resort in Windsor County is best for families?

If you are looking for a family-friendly hotel, resort, or vacation home in Windsor County, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in Windsor County:

How many hotels, resorts, or rentals are available in Windsor County?

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 1975 in the Windsor County area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Windsor County.


People Also Ask

There are 139 hotels in Windsor County 18 resorts, and 1291 rentals

Recently Booked Hotels, Resorts, or Rentals in Windsor County