Bespokeusatravel - Vacation Rentals in Windsor County

Property Image From US $164
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Windsor County

Over 2028+ Luxury Places to Stay in or Near Windsor County
Property Image From US $3,623
         

10.0 (34 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $3,336
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $3,151
         

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8.0 (31 Reviews)
Apartment
  • Parking
  • Pool
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Windsor County

Over 533+ Top-Rated Vacation Rentals with a Pool in or Near Windsor County

Pet-Friendly Vacation Rentals in Windsor County

Over 493+ Pet-Friendly Vacation Rentals in or Near Windsor County
Property Image From US $322
         

Property Image From US $145
         

9.6 (542 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $1,364
         

Large Vacation Homes & Villas in Windsor County

Over 503+ Large Vacation Homes & Villas in or Near Windsor County
Property Image From US $500
         

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10.0 (2 Reviews)
House
  • Parking
  • Pool
  • Private Pool
Property Image From US $435
         

9.4 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From US $810
         

9.4 (23 Reviews)
Ski Chalet
  • Parking
  • TV
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Windsor County

Over 91+ Wheelchair Accessible Vacation Homes in or Near Windsor County
Property Image From US $185
         

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9.7 (30 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
Property Image From US $338
         

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10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From US $482
         

10.0 (3 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From US $279
         

Windsor County Varoom and Airbnb Places to Stay Under $200

Over 233+ Windsor County Varoom and Airbnb Places to Stay Under $200
Property Image From US $192
         

10.0 (33 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From US $193
         

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10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • Security/Safety
  • Sports/Activities
Property Image From US $193
         

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9.8 (251 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From US $191
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From US $135
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Windsor County

Over 1080+ Instantly Bookable Vacation Homes in or Near Windsor County
Property Image From US $372
         

10.0 (8 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Balcony/Terrace

About Windsor County Vacation Rentals

With more than 2037 Windsor County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Windsor County, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor County. Places to stay near Windsor County are 1122.39 ft² on average, with prices averaging $580 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Windsor County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windsor County

Type Count
Vacation Homes 1019
Holiday Apartments 184
Hotels with Suites 137
Cabin Rentals 114
Ski Chalet Rentals 57
Others 39
Cottages 38
B&B 30
Resorts 18
Villas 6

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

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor County.

Weather in Windsor County

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