25+ Vacation Rentals Near Isle of Wight Bay |
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Montgomery Cottages - Vacation Rentals in Isle of Wight Bay

Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette From US $210
         

10.0 (1 Review)
Cottage
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette
  • Air Conditioner
  • TV
  • View

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Shore Point Cottages From US $204
         

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9.0 (447 Reviews)
House
Shore Point Cottages
  • Air Conditioner
  • Parking
  • Pet Friendly

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Shore Point Cottages From US $139
         

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9.4 (303 Reviews)
Cottage
Shore Point Cottages
  • Air Conditioner
  • Parking
  • Pet Friendly

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Charming cottage near beach/boardwalk with modern amenities, AC, WiFi From US $224
         

9.0 (2 Reviews)
Cottage
Charming cottage near beach/boardwalk with modern amenities, AC, WiFi
  • Air Conditioner
  • Parking
  • TV

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208 Cottage 4 Green 2nd unit From US $329
         

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8.8 (8 Reviews)
Apartment
208 Cottage 4 Green 2nd unit
  • Air Conditioner
  • Parking
  • Security/Safety

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Charming cottage near the boardwalk & beach with AC, WiFi, kitchen From US $209
         

5.4 (3 Reviews)
Cottage
Charming cottage near the boardwalk & beach with AC, WiFi, kitchen
  • Air Conditioner
  • TV
  • View

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Cottages on St. Louis #3 From US $509
         

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8.0 (1 Review)
House
Cottages on St. Louis #3
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

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Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms. From US $157
         

10.0 (6 Reviews)
Cottage
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
  • Air Conditioner
  • Pet Friendly
  • Pool

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208 Cottage 3 Green 1st floor unit From US $394
         

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7.8 (14 Reviews)
Apartment
208 Cottage 3 Green 1st floor unit
  • Air Conditioner
  • Parking
  • Security/Safety

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Deluxe Cottage - 2 Bedroom Cabin 4 - Deluxe Cottage with two bedrooms. From US $157
         

10.0 (3 Reviews)
Cottage
Deluxe Cottage - 2 Bedroom Cabin 4 - Deluxe Cottage with two bedrooms.
  • Air Conditioner
  • Pet Friendly
  • Pool

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208 Cottage 5 Yellow 1st unit From US $426
         

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7.8 (12 Reviews)
Apartment
208 Cottage 5 Yellow 1st unit
  • Air Conditioner
  • Parking
  • View

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Deluxe Cottage - 2 Bedroom Cabin 2 - Deluxe Cottage with two bedrooms. From US $157
         

10.0 (3 Reviews)
Cottage
Deluxe Cottage - 2 Bedroom Cabin 2 - Deluxe Cottage with two bedrooms.
  • Air Conditioner
  • Pet Friendly
  • Pool

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Cottages on St. Louis #1 From US $363
         

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1.0 (1 Review)
House
Cottages on St. Louis #1
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility

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Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms. From US $211
         

9.4 (12 Reviews)
Cottage
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
  • Air Conditioner
  • Pet Friendly
  • Pool

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The Cottage From US $438
         

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New
House
The Cottage
  • View
  • Balcony/Terrace
  • Security/Safety

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Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower From US $196
         

8.8 (9 Reviews)
Cottage
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cottages on St. Louis #2 From US $355
         

New
House
Cottages on St. Louis #2
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety

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Deluxe Cottage - 2 Bedroom Cabin 3 - Deluxe Cottage with two bedrooms. From US $157
         

8.0 (3 Reviews)
Cottage
Deluxe Cottage - 2 Bedroom Cabin 3 - Deluxe Cottage with two bedrooms.
  • Air Conditioner
  • Pet Friendly
  • Pool

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Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower From US $292
         

4.6 (7 Reviews)
Cottage
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
  • Air Conditioner
  • Parking
  • Pet Friendly

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Perfect 1 Bedroom Cottage Close to the Famous Ocean City Boardwalk! From US $120
         

4.3 (3 Reviews)
Cottage
Perfect 1 Bedroom Cottage Close to the Famous Ocean City Boardwalk!
  • TV
  • Bedding/Linens
  • Child Friendly

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Charming 3 Bedroom Cottage in Downtown Ocean City Close to Boardwalk! From US $209
         

4.1 (7 Reviews)
Cottage
Charming 3 Bedroom Cottage in Downtown Ocean City Close to Boardwalk!
  • TV
  • Balcony/Terrace
  • Bedding/Linens

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Stunning 2 Bedroom Cottage Close to the Ocean City Boardwalk! From US $124
         

4.0 (5 Reviews)
Cottage
Stunning 2 Bedroom Cottage Close to the Ocean City Boardwalk!
  • TV
  • Bedding/Linens
  • Child Friendly

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Bayside Family Cottages bayside life and easy walk to the beach and boardwalk ! From US $440
         

9.6 (4 Reviews)
Cottage
Bayside Family Cottages bayside life and easy walk to the beach and boardwalk !
  • Air Conditioner
  • Parking
  • Pet Friendly

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STAY SAFE in OC! Bayside Family Cottages walk to the beach and boardwalk . From US $250
         

4.0 (6 Reviews)
Cottage
STAY SAFE in OC! Bayside Family Cottages walk to the beach and boardwalk .
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

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

Weather in Isle of Wight Bay

View the weather forecast for Isle of Wight Bay before booking your Isle of Wight Bay Vacation Rentals to confirm your best time to go.

December - February
High 55°F       Low 28°F
March - May
High 72°F       Low 34°F
June - August
High 88°F       Low 63°F
September - November
High 78°F       Low 35°F

Top Attractions Around Isle of Wight Bay, MD

Montgomerycottages offers a large selection of top attractions around Isle of Wight Bay. Research things to do on your vacation before you visit Isle of Wight Bay.


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

Other Places to Stay Near Isle of Wight Bay, MD


Ocean City 7,920 Properties Roland E. Powell Convention Center 6,035 Properties

Complexes around Isle of Wight Bay, MD


Sea Watch Ocean City 206 Properties Thunder Island 35 Properties Belmont Ocean 29 Properties Ocean Hideaway 26 Properties Sunburst 7 Properties Wilmington Terrace 7 Properties Alameda 4 Properties Frogs 4 Properties White Marlin 4 Properties Alexander 3 Properties Comfort Inn Boardwalk 3 Properties Gateway Hotel 3 Properties Surfcrest 3 Properties Village West 3 Properties Laguna Vista 1 Properties
See More Complexes