
Isle of Wight Holiday Rentals
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Our top choices for Isle of Wight holiday rentals

1. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
2. Shore Point Cottages
Shore Point Cottages
3. Ocean City Townhome by Beach Bayside
Ocean City Townhome by Beach Bayside
4. Canal front with boat slip, boat ramp, WiFi, and roku streaming TV
Canal front with boat slip, boat ramp, WiFi, and roku streaming TV
5. Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
Ocean City Maryland Condo, The Mermaid Lounge! Ocean side 50 steps to the beach!
6. On Main Street - Apartment C - Berlin, MD
On Main Street - Apartment C - Berlin, MD
7. Beach Paradise 105 - Beach Home at Broad Marsh OC
Beach Paradise 105 - Beach Home at Broad Marsh OC
8. Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
Beach Days & Bay Sunsets. Your Easy OCMD Escape! Raffles Unit 339 N
9. Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View
10. BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
11. Beach Paradise VI-Downtown Waterfront Bayview, Luxury Boardwalk Condo with POOL!
Beach Paradise VI-Downtown Waterfront Bayview, Luxury Boardwalk Condo with POOL!
12. Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
Studio Charm w/ Deck, Fireplace & Fooseball!: Walk to Beach, Boardwalk & Dining!
13. Pet-Friendly Cottage on 1.5 Acres Near Beaches!
Pet-Friendly Cottage on 1.5 Acres Near Beaches!
14. BeachBox® II • Panoramic Inlet Views • Bayside Pool • Assateague House 411
BeachBox® II • Panoramic Inlet Views • Bayside Pool • Assateague House 411
15. ⛱Beach Days & Quiet Nights | 3BR Home Near Bethany
⛱Beach Days & Quiet Nights | 3BR Home Near Bethany
16. BeachBox® V • 5th-Floor Oceanfront • Expansive Views • East Winds 502
BeachBox® V • 5th-Floor Oceanfront • Expansive Views • East Winds 502
17. Direct Oceanfront condo- AMAZING VIEWS & GREAT AMENITIES!
Direct Oceanfront condo- AMAZING VIEWS & GREAT AMENITIES!
18. Clean, modern and well-equipped Ocean City condo
Clean, modern and well-equipped Ocean City condo
19. Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
20. Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding ReviewsFind holiday rentals that suit your style
Top Isle of Wight Hotel Reviews

Holiday Inn Ocean City by IHG
Find out more about Isle of Wight
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Isle of Wight holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Isle of Wight. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Isle of Wight. Seeing all the best attractions is bound to make you fall in love with Isle of Wight. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Isle of Wight short-term rentals, that won’t be hard to do.
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- Visit Deal Island
- Visit Fruitland
- Visit Ocean Pines
- Bordeleau Winery
- Roland E. Powell Convention Center
- Baja Amusements
- Choptank River Lighthouse
- Ward Museum of Wildfowl Art
- Christ Episcopal Church
- Assawoman Bay
- Poplar Hill Mansion
- Glenriddle Golf Club
- Jolly Roger Amusement Park
- Bill Burton Fishing Pier State Park
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