5910+ Vacation Rentals Near Cape Windsor |
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Pawleys Island Vacation Rental - Vacation Rentals in Cape Windsor

Ocean Front, North Ocean City, Maryland From US $481
         

10.0 (46 Reviews)
Condo
Ocean Front, North Ocean City, Maryland
  • Air Conditioner
  • Parking
  • Pool

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The Capri From US $87
         

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6.1 (13 Reviews)
Apartment
The Capri
  • Air Conditioner
  • Parking
  • Pool

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2 Mi to Beach: Gem w/Enclosed Patio in Selbyville From US $306
         

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10.0 (3 Reviews)
Apartment
2 Mi to Beach: Gem w/Enclosed Patio in Selbyville
  • Air Conditioner
  • Parking
  • Pool

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Upscale Beach & Golf Getaway At Bayside Resort From US $394
         

9.8 (108 Reviews)
Villa
Upscale Beach & Golf Getaway At Bayside Resort
  • Air Conditioner
  • Parking
  • Pool

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Lighthouse Condos From US $61
         

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7.4 (15 Reviews)
House
Lighthouse Condos
  • Air Conditioner
  • Parking
  • Child Friendly

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Club Ocean Villas II by Coolvacay From US $274
         

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8.6 (59 Reviews)
Apartment
Club Ocean Villas II by Coolvacay
  • Air Conditioner
  • Parking
  • Pool

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Perfect Sunsets-Direct Bay Front Condo! Crab and fish from the large deck. From US $236
         

9.8 (107 Reviews)
Condo
Perfect Sunsets-Direct Bay Front Condo! Crab and fish from the large deck.
  • Air Conditioner
  • Parking
  • TV

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Fenwick Island Home with Canalfront Deck Less Than 1Mi to BCH From US $289
         

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7.0 (1 Review)
House
Fenwick Island Home with Canalfront Deck Less Than 1Mi to BCH
  • Parking
  • View
  • Wheelchair Accessible

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Atlantis 1608 2 Bedroom Condo by RedAwning From US $179
         

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New
Condo
Atlantis 1608 2 Bedroom Condo by RedAwning
  • Pool
  • View
  • Wheelchair Accessible

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🏖️ 5 Bedroom Penthouse Ocean Views, Renovated, Pool, Stunning Ocean Views🏖️ From US $554
         

9.8 (78 Reviews)
Condo
🏖️ 5 Bedroom Penthouse Ocean Views, Renovated, Pool, Stunning Ocean Views🏖️
  • Air Conditioner
  • Parking
  • Pool

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FALL End of Season PRICE DROP⬇️ Get All Remaining Nts from $99 w/Low Fees From US $199
         

10.0 (138 Reviews)
Condo
FALL End of Season PRICE DROP⬇️ Get All Remaining Nts from $99 w/Low Fees
  • Air Conditioner
  • Parking
  • Pool

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Capri Ocean Front Family Beach Vacation Resort From US $375
         

10.0 (47 Reviews)
Condo
Capri Ocean Front Family Beach Vacation Resort
  • Air Conditioner
  • Parking
  • Pool

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BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL! From US $212
         

9.8 (131 Reviews)
Condo
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
  • Air Conditioner
  • Parking
  • Pool

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Charming canal front home, quiet neighborhood, one mile from ocean, Prof. Clean. From US $283
         

10.0 (112 Reviews)
House
Charming canal front home, quiet neighborhood, one mile from ocean, Prof. Clean.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Gorgeous Direct Oceanfront From US $572
         

9.8 (36 Reviews)
Condo
Gorgeous Direct Oceanfront
  • Air Conditioner
  • Parking
  • Pool

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BEST OCEAN&BAY VIEW 2BR2BTH CALL HOST NOW FOR DISCOUNTS JUN JUL AUG. FREE LINENS From US $465
         

9.8 (25 Reviews)
Condo
BEST OCEAN&BAY VIEW 2BR2BTH CALL HOST NOW FOR DISCOUNTS JUN JUL AUG. FREE LINENS
  • Air Conditioner
  • Parking
  • Pool

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Newly Updated Large 3br Bayside Townhome Perfect for Families! From US $434
         

9.6 (48 Reviews)
House
Newly Updated Large 3br Bayside Townhome Perfect for Families!
  • Air Conditioner
  • Parking
  • TV

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Nicely Appointed Beachfront Condo with Incredible Views and Indoor Pool! From US $228
         

9.4 (166 Reviews)
Condo
Nicely Appointed Beachfront Condo with Incredible Views and Indoor Pool!
  • Air Conditioner
  • Parking
  • Pool

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Dazzling Views Perfect Location Ocean Front with Pool Fabulous Balcony Sleeps 6 From US $249
         

9.8 (51 Reviews)
Condo
Dazzling Views Perfect Location Ocean Front with Pool Fabulous Balcony Sleeps 6
  • Air Conditioner
  • Parking
  • Pool

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*Beach View* Free Wifi, Elevator, Lots of Free Parking From US $493
         

9.6 (34 Reviews)
Condo
*Beach View* Free Wifi, Elevator, Lots of Free Parking
  • Air Conditioner
  • Parking
  • TV

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Ocean Front - 3 Bedroom w/2 King Rooms - Amazing Views - Perfect for Families! From US $237
         

10.0 (226 Reviews)
Condo
Ocean Front - 3 Bedroom w/2 King Rooms - Amazing Views - Perfect for Families!
  • Air Conditioner
  • Parking
  • TV

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Sea Watch 1314 is a gorgeous newly remodeled Ocean Front Condo in famous Ocean C From US $428
         

9.8 (58 Reviews)
Condo
Sea Watch 1314 is a gorgeous newly remodeled Ocean Front Condo in famous Ocean C
  • Air Conditioner
  • Parking
  • Pool

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Luxury 2-story, 3 bedrooms plus den house with free WiFi, linen included, backyard for pet friendly, located in a family-friendly neighborhood on the bayside just a few blocks from the beach! From US $346
         

8.6 (22 Reviews)
House
Luxury 2-story, 3 bedrooms plus den house with free WiFi, linen included, backyard for pet friendly, located in a family-friendly neighborhood on the bayside just a few blocks from the beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Affordable 2-Story Penthouse w/Panoramic Ocean And Bay Views From US $272
         

9.6 (86 Reviews)
Condo
Affordable 2-Story Penthouse w/Panoramic Ocean And Bay Views
  • Air Conditioner
  • Parking
  • Pool

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

Weather in Cape Windsor

View the weather forecast for Cape Windsor before booking your Cape 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

Top Attractions Around Cape Windsor, DE

Pawleysislandvacationrental offers a large selection of top attractions around Cape Windsor. Research things to do on your vacation before you visit Cape Windsor.


Ocean City Boardwalk Ocean City Beach Jolly Roger Amusement Park Maryland Beach Bethany Beach Boardwalk Casino at Ocean Downs Roland E. Powell Convention Center Jolly Roger at the Pier Carousel Ice Skating Rink Trimper's Rides Northside Park Ocean City Inlet Main Street Berlin Inlet Park Gold Coast Mall Delaware Seashore State Park Bayside Resort Golf Club Oceanic Fishing Pier Ocean City Life-Saving Station Museum Assawoman Bay

Cape Windsor Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Cape Windsor?

There are a lot of options in Cape Windsor. If you plan on staying in the Cape Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cape Windsor:

How many vacation rentals are available in Cape Windsor?

Currently, the total number of properties listed in 2026 is over 5910 in the Cape Windsor area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cape Windsor.