Rent The Cottages - Vacation Rentals in Windsor

Afton Cabin From US $340
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
Chestnut Inn at Oquaga Lake From US $289
         

9.0 (52 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Mtn-View Catskills Cabin on Delaware River! From US $629
         

10.0 (9 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Welcome to Osborne Creek! From US $107
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • TV

Luxury Places to Stay in Windsor

Over 55+ Luxury Places to Stay in or Near Windsor
Lake Front Oquaga Lake Catskills Upstate NY n5 Bedroom From US $683
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Afton Cabin From US $580
         

10.0 (16 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
West Branch Delaware River Cozy Cabin Retreat! From US $501
         

|
New
House
  • Parking
  • Accessibility
  • Security/Safety
River Views & Covered Deck: Susquehanna Home! From US $430
         

Top-Rated Vacation Rentals with a Pool in Windsor

Over 1+ Top-Rated Vacation Rentals with a Pool in or Near Windsor

Pet-Friendly Vacation Rentals in Windsor

Over 20+ Pet-Friendly Vacation Rentals in or Near Windsor
Your Tranquil Oasis on the Susquehanna River From US $307
         

9.8 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Rivers Edge of the West Branch Delaware River w Private Boat Launch From US $178
         

3 Season Getaway Right on the River! From US $173
         

Relaxing West Branch Cabin From US $316
         

10.0 (24 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Quaint Cottage - Amazing Views, Great Swimming on Oquaga Lake From US $650
         

10.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Windsor on PetFriendly.io

Large Vacation Homes & Villas in Windsor

Over 8+ Large Vacation Homes & Villas in or Near Windsor
Victorian Cottage on Oquaga Lake From US $516
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Parking
  • TV
Waterfront Home w/Deck & Canoe in Afton From US $240
         

8.0 (4 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Tentrr Signature Site - Little Sit Farm Cosmic Glamping Site From US $138
         

5.0 (1 Review)
RV Rental
  • Pet Friendly
  • Balcony/Terrace
  • Child Friendly
Secluded Get Away From US $250
         

4.9 (9 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Oquaga Lake House Rental From US $250
         

4.5 (10 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Spacious 5-bedroom river house in charming Deposit From US $374
         

9.6 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Clean and furnished pet free From US $350
         

New
Other
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Windsor Varoom and Airbnb Places to Stay Under $200

Over 14+ Windsor Varoom and Airbnb Places to Stay Under $200
Riverfront Cabin West Branch Delaware River From US $173
         

9.8 (118 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Waterfront Home with Deck and Canoe in Afton From US $162
         

|
10.0 (1 Review)
House
  • Parking
  • Accessibility
  • Security/Safety
Colonial Brick Inn & Suites From US $112
         

7.6 (482 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Waterfront Properties vacation rental From US $170
         

9.8 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming 3-bedroom cottage in Windsor. From US $181
         

Tentrr Signature Site - Agfa Lake From US $125
         

5.0 (1 Review)
RV Rental
  • Pet Friendly
  • Child Friendly

Instantly Bookable Vacation Homes in Windsor

Over 6+ Instantly Bookable Vacation Homes in or Near Windsor
Riverfront Retreat w/Near Boat Launch in Nineveh! From US $327
         

Hot Tub & Watercrafts: Lakefront Catskills Getaway From US $444
         

Lake Front House on Private lake From US $284
         

9.8 (54 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace

About Windsor Vacation Rentals

With more than 64 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rentthecottages 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.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Rentthecottages Windsor, 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. Places to stay near Windsor are 689.02 ft² on average, with prices averaging $302 a night.

Rentthecottages makes it easy and safe to find and compare vacation rentals in Windsor 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

Type Count
Vacation Homes 31
Cabin Rentals 11
Others 7
Hotels with Suites 5
Cottages 4
Holiday Apartments 2

Use these Quick Filters to Find a Vacation Rental in Windsor

Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages 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.

Weather in Windsor

View the weather forecast for Windsor before booking your Windsor 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