Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Near the bay, this 2-bedroom condo accommodates 6 guests and features 2 bathrooms. It includes 1 separate living room and 1 hot tub. Enjoy activities like swimming, fishing, and kayaking nearby. Golf enthusiasts can find courses close by, while attractions such as 2nd Time Designs and the Nanticoke Indian Museum await your visit.
Highlights
Made for relaxation
Top-rated for comfort — guests feel right at home here.
Pickleball on-site
A rare find — enjoy pickleball without leaving the property.
2 bedrooms2 bathroomsSleeps 6
Popular amenities
Swimming pool
Onsite parking available
Air-conditioning
Balcony
Washing machine
Hot tub on site
Explore the area
Millsboro, DE
beach near Lingo Point
Place, beach near Lingo Point
2 min drive
Nanticoke Indian Museum
Place, Nanticoke Indian Museum
6 min drive
Baywood Greens
Place, Baywood Greens
7 min drive
Georgetown, DE (GED-Sussex County)
Airport, Georgetown, DE (GED-Sussex County)
26 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 2
1 Queen Bed and 1 Single Bed
Living Room 1
1 Double Sofa Bed
Master Bedroom
1 King Bed
2 bathrooms
Bathroom 2
Towels provided · Bathtub or shower · Bathtub · Toilet
Master Bathroom
Towels provided · Bathtub or shower · Bathtub · Toilet
Spaces
Kitchen
Balcony
Number of living rooms
Outdoor play area
Dining area
About this property
Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach
Come enjoy and relax at The Peninsula - a beautiful and upscale gated country club and golf course community! The East Coast's most award-winning resort community is located on the Indian River Bay close to Rehoboth and Lewes beaches. This perfect blend of sophisticated yet comfortable resort living awaits you! Vacation at The Peninsula in this deluxe two-bedroom, two-bathroom condominium. Enjoy your morning coffee on the screened porch while watching the sun rise. If you prefer to eat in, there is a fully equipped kitchen with gas stove. The condominium comfortably sleeps up to six people. The master suite has a king bed with a sitting area and private bath. The second bedroom provides a queen bed and twin daybed. The Peninsula condominium is excellent for families looking for a worry-free vacation - the 3 indoor/outdoor pools and hot tubs (wave pool and adults-only pool available - from Memorial Day to Labor Day only), game center, playground, tennis, and basketball courts all offer an activity to please the whole group! There is a separate amenities fee for use of the pools and other amenities that is paid to the community association at the Concierge Desk in the Activity Center. For the outdoor-loving guests, the private bay beach is a short walk away. Enjoy fishing and crabbing as well as scenic nature trails. Kayaks and SUP (available for an additional charge) are a perfect way to take in the breathtaking views of the bay. The resort also offers pickle ball, bocce courts, volleyball, children's activities, fitness classes and so much more. Take advantage of casual dining at The Terrace Grille or fine dining (not available to rental guests on Friday or Saturday) at The Clubhouse. For the golfers, here is your chance to play a Jack Nicklaus Signature Golf Course for an additional fee. Guests can drive a short distance to the tax-free shopping at Tanger Outlets, downtown Rehoboth Beach with a boardwalk or Historic Lewes. No smoking allowed. Club Amenity Fees due with final payments. Some Restrictions Apply. Pets are not allowed at this property. Peninsula rules allow for a maximum of 2 cars. We have added 2 bicycles for your use, they are in the garage and there is a picture of them in our listing. Our Community Association requires a 7 day stay from Memorial Day to Labor Day. The rest of the year there is a 3 day minimum stay.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
About the area
Millsboro
Millsboro is home to this condo. While the natural beauty of Cape Henlopen State Park and Rehoboth Beach can be enjoyed by anyone, those looking for an activity can explore Cape May - Lewes Ferry.
2nd Time Designs and Midway Speedway are also worth visiting. With kayaking, fishing and swimming nearby, you'll find plenty of adventures in the water.
Millsboro, DE
What's nearby
beach near Lingo Point - 2 min drive - 1.1 km
2nd Time Designs - 5 min drive - 5.9 km
Nanticoke Indian Museum - 6 min drive - 6.5 km
Baywood Greens - 7 min drive - 7.2 km
Baywood Greens Golf Course - 16 min drive - 18.0 km
Getting around
Georgetown, DE (GED-Sussex County) - 33 min drive
Restaurants
Wawa - 6 min drive
Royal Farms - 7 min drive
McDonald's - 6 min drive
Dunkin' - 6 min drive
Paradise Pub - 9 min drive
Frequently asked questions
Does Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach have a pool?
Yes, this property has a pool.
How much does it cost to stay at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?
As of 2 Sept, 2026, prices found for a 1-night stay for 2 adults at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach on 1 Jan, 2027 start from S$857, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach pet-friendly?
No, pets are not allowed at this property.
How much is parking at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?
On-site parking is available at the property.
What time is check-in at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?
Check-in begins at 3:00 PM.
What time is check-out at Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach?
Checkout is at 10:00 AM.
Where is Windswept Dr Condo in a quiet, golf course community close to Rehoboth Beach located?
Situated in Millsboro, this condo building is 2.9 mi (4.7 km) from 2nd Time Designs and within 6 miles (10 km) of Nanticoke Indian Museum and Baywood Greens. Delaware Seashore State Park and Baywood Greens Golf Course are also within 12 miles (20 km).
About the host
Hosted by John Petrosino
Languages:
English
Premier Host
They consistently provide great experiences for their guests