Vacation rentals in Isle of Wight Bay, MD

200 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Isle of Wight Bay, MD

Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more - Isle of Wight Bay, MD

Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more

Apartment, Isle of Wight Bay

Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more is a apartment in Isle of Wight Bay, with easy beach access. This stay gives travelers a comfortable base…

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About Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more

Jamaica Daybreak-Great Location,Cozy studio in amazing Ocean City W/AC,WiFi&more is a apartment in Isle of Wight Bay, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, dryer, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,209.

From$125/night
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Great 2 Bedroom, 1 bath within walking distance to beach and boardwalk - Isle of Wight Bay, MD

Great 2 Bedroom, 1 bath within walking distance to beach and boardwalk

Condo, Isle of Wight Bay

Great 2 Bedroom, 1 bath within walking distance to beach and boardwalk is a condo in Isle of Wight Bay, with easy beach access, kitchen access, and room for a group. This stay gives…

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About Great 2 Bedroom, 1 bath within walking distance to beach and boardwalk

Great 2 Bedroom, 1 bath within walking distance to beach and boardwalk is a condo in Isle of Wight Bay, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,470.

From$131/night
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Water view condo with peaceful balcony, open layout, smart TVs, games, & W/D - Isle of Wight Bay, MD

Water view condo with peaceful balcony, open layout, smart TVs, games, & W/D

Condo, Isle of Wight Bay

Water view condo with peaceful balcony, open layout, smart TVs, games, & W/D is a condo in Isle of Wight Bay, with outdoor space and kitchen access. This stay gives travelers a comfortable…

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About Water view condo with peaceful balcony, open layout, smart TVs, games, & W/D

Water view condo with peaceful balcony, open layout, smart TVs, games, & W/D is a condo in Isle of Wight Bay, with outdoor space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,783.

From$134/night
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Waterfront ground level condo on 28th St. with Boat slip - bring the boat or jet skis! Bayshore #2 - Isle of Wight Bay, MD

Waterfront ground level condo on 28th St. with Boat slip - bring the boat or jet skis! Bayshore #2

Condo, Isle of Wight Bay

Waterfront ground level condo on 28th St. with Boat slip - bring the boat or jet skis! Bayshore #2 is a condo in Isle of Wight Bay, with easy beach access and kitchen access. This stay…

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About Waterfront ground level condo on 28th St. with Boat slip - bring the boat or jet skis! Bayshore #2

Waterfront ground level condo on 28th St. with Boat slip - bring the boat or jet skis! Bayshore #2 is a condo in Isle of Wight Bay, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,561.

From$136/night
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Browse Waterfront Vacation Rentals in Isle of Wight Bay, MD

Discover vacation rentals close to the coast, water, and beach areas around Isle of Wight Bay, MD.

Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC - Isle of Wight Bay, MD

Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC

Holiday Home, Isle of Wight Bay

Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC is a holiday home in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC

Vantage Point 5-Baywater 28th St, Free WiFi, W/D, AC is a holiday home in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,681.

From$182/night
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Lovely direct bayfront two bedroom townhouse with gorgeous views! - Isle of Wight Bay, MD

Lovely direct bayfront two bedroom townhouse with gorgeous views!

Holiday Home, Isle of Wight Bay

Lovely direct bayfront two bedroom townhouse with gorgeous views! is a holiday home in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Lovely direct bayfront two bedroom townhouse with gorgeous views!

Lovely direct bayfront two bedroom townhouse with gorgeous views! is a holiday home in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,959.

From$192/night
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Modernized Bayfront Retreat Near Jolly Roger, Boat Slip Available - Isle of Wight Bay, MD

Modernized Bayfront Retreat Near Jolly Roger, Boat Slip Available

Condo, Isle of Wight Bay

Modernized Bayfront Retreat Near Jolly Roger, Boat Slip Available is a condo in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Modernized Bayfront Retreat Near Jolly Roger, Boat Slip Available

Modernized Bayfront Retreat Near Jolly Roger, Boat Slip Available is a condo in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,898.

From$193/night
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Bayside Waterfront Retreat in Ocean City! - Isle of Wight Bay, MD

Bayside Waterfront Retreat in Ocean City!

Condo, Isle of Wight Bay

Bayside Waterfront Retreat in Ocean City! is a condo in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Bayside Waterfront Retreat in Ocean City!

Bayside Waterfront Retreat in Ocean City! is a condo in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,326.

From$213/night
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Browse Vacation Rentals with a Pool in Isle of Wight Bay, MD

Add a pool to the search when you want an easy place to cool off between outings.

End-unit townhome with resort amenities, water view, balcony, fireplace, & AC - Isle of Wight Bay, MD

End-unit townhome with resort amenities, water view, balcony, fireplace, & AC

Holiday Home, Isle of Wight Bay

End-unit townhome with resort amenities, water view, balcony, fireplace, & AC is a holiday home in Isle of Wight Bay, with pool access, outdoor space, and kitchen access. This stay gives…

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About End-unit townhome with resort amenities, water view, balcony, fireplace, & AC

End-unit townhome with resort amenities, water view, balcony, fireplace, & AC is a holiday home in Isle of Wight Bay, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,134.

From$164/night
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Fabulous one bedroom condo with pool and courtyard, 10-min walk to the beach - Isle of Wight Bay, MD

Fabulous one bedroom condo with pool and courtyard, 10-min walk to the beach

Condo, Isle of Wight Bay

Fabulous one bedroom condo with pool and courtyard, 10-min walk to the beach is a condo in Isle of Wight Bay, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Fabulous one bedroom condo with pool and courtyard, 10-min walk to the beach

Fabulous one bedroom condo with pool and courtyard, 10-min walk to the beach is a condo in Isle of Wight Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,653.

From$180/night
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Beautifully renovated condo, close to the boardwalk - away from the noise! - Isle of Wight Bay, MD

Beautifully renovated condo, close to the boardwalk - away from the noise!

Condo, Isle of Wight Bay

Beautifully renovated condo, close to the boardwalk - away from the noise! is a condo in Isle of Wight Bay, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Beautifully renovated condo, close to the boardwalk - away from the noise!

Beautifully renovated condo, close to the boardwalk - away from the noise! is a condo in Isle of Wight Bay, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,859.

From$190/night
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2 bedroom, 2 bath, 28th bayside with pool and tennis court! - Isle of Wight Bay, MD

2 bedroom, 2 bath, 28th bayside with pool and tennis court!

Condo, Isle of Wight Bay

2 bedroom, 2 bath, 28th bayside with pool and tennis court! is a condo in Isle of Wight Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base…

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About 2 bedroom, 2 bath, 28th bayside with pool and tennis court!

2 bedroom, 2 bath, 28th bayside with pool and tennis court! is a condo in Isle of Wight Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,119.

From$201/night
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Best Isle of Wight Bay, MD vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Atlantic Breeze Motel & Apartments - Isle of Wight Bay, MD

Atlantic Breeze Motel & Apartments

Apartment, Isle of Wight Bay

Atlantic Breeze Motel & Apartments is a apartment in Isle of Wight Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Atlantic Breeze Motel & Apartments

Atlantic Breeze Motel & Apartments is a apartment in Isle of Wight Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,062.

From$133/night
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Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards! - Isle of Wight Bay, MD

Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards!

Cottage, Isle of Wight Bay

Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards! is a cottage in Isle of Wight Bay, with easy beach access, outdoor space, and parking. This stay gives…

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About Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards!

Boho Beach Cottage- Quiet, Deck, Private parking, Bikes- 1 mi to Beach & Boards! is a cottage in Isle of Wight Bay, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,853.

From$193/night
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Vantage Point 5 Townhouse - Isle of Wight Bay, MD

Vantage Point 5 Townhouse

Holiday Home, Isle of Wight Bay

Vantage Point 5 Townhouse is a holiday home in Isle of Wight Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Vantage Point 5 Townhouse

Vantage Point 5 Townhouse is a holiday home in Isle of Wight Bay, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, parking, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,434.

From$200/night
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ABOUT 5 BLOCKS FROM THE BEACH/ OCEAN / NORTH END OF BOARDWALK - Isle of Wight Bay, MD

ABOUT 5 BLOCKS FROM THE BEACH/ OCEAN / NORTH END OF BOARDWALK

Condo, Isle of Wight Bay

ABOUT 5 BLOCKS FROM THE BEACH/ OCEAN / NORTH END OF BOARDWALK is a condo in Isle of Wight Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base…

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About ABOUT 5 BLOCKS FROM THE BEACH/ OCEAN / NORTH END OF BOARDWALK

ABOUT 5 BLOCKS FROM THE BEACH/ OCEAN / NORTH END OF BOARDWALK is a condo in Isle of Wight Bay, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,080.

From$214/night
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Best Pet-Friendly Vacation Rentals in Isle of Wight Bay, MD

Bring your pet along with stays that welcome four-legged travelers.

Ocean Pines 2BR 1BA Cottage with Fire Pit - Isle of Wight Bay, MD

Ocean Pines 2BR 1BA Cottage with Fire Pit

Holiday Home, Isle of Wight Bay

Ocean Pines 2BR 1BA Cottage with Fire Pit is a holiday home in Isle of Wight Bay, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base…

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About Ocean Pines 2BR 1BA Cottage with Fire Pit

Ocean Pines 2BR 1BA Cottage with Fire Pit is a holiday home in Isle of Wight Bay, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,932.

From$185/night
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Adorable 2 bedroom townhouse on canal with free WiFi and boat dock located downtown on the bayside! - Isle of Wight Bay, MD

Adorable 2 bedroom townhouse on canal with free WiFi and boat dock located downtown on the bayside!

Holiday Home, Isle of Wight Bay

Adorable 2 bedroom townhouse on canal with free WiFi and boat dock located downtown on the bayside! is a holiday home in Isle of Wight Bay, with easy beach access, parking, and kitchen…

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About Adorable 2 bedroom townhouse on canal with free WiFi and boat dock located downtown on the bayside!

Adorable 2 bedroom townhouse on canal with free WiFi and boat dock located downtown on the bayside! is a holiday home in Isle of Wight Bay, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,029.

From$216/night
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Sea Robin 207 by Seaside Vacations & Sales - Isle of Wight Bay, MD

Sea Robin 207 by Seaside Vacations & Sales

Condo, Isle of Wight Bay

Sea Robin 207 by Seaside Vacations & Sales is a condo in Isle of Wight Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sea Robin 207 by Seaside Vacations & Sales

Sea Robin 207 by Seaside Vacations & Sales is a condo in Isle of Wight Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,217.

From$239/night
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Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC - Isle of Wight Bay, MD

Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC

Holiday Home, Isle of Wight Bay

Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC is a holiday home in Isle of Wight Bay, with pet-friendly space, easy beach access, and parking. This stay gives travelers a…

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About Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC

Sea Jay Townhouse 616C-Baywater 28th St, Free WiFi, W/D, AC is a holiday home in Isle of Wight Bay, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,296.

From$253/night
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Best Isle of Wight Bay, MD vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

3BR/2BA Ocean Pines golf course home near Yacht Club, marina & pools—minutes to Ocean City beaches! - Isle of Wight Bay, MD

3BR/2BA Ocean Pines golf course home near Yacht Club, marina & pools—minutes to Ocean City beaches!

Holiday Home, Isle of Wight Bay

3BR/2BA Ocean Pines golf course home near Yacht Club, marina & pools—minutes to Ocean City beaches! is a holiday home in Isle of Wight Bay, with pool access, easy beach access, and kitchen…

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About 3BR/2BA Ocean Pines golf course home near Yacht Club, marina & pools—minutes to Ocean City beaches!

3BR/2BA Ocean Pines golf course home near Yacht Club, marina & pools—minutes to Ocean City beaches! is a holiday home in Isle of Wight Bay, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,050.

From$134/night
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WATER FRONT CONDO - Isle of Wight Bay, MD

WATER FRONT CONDO

Condo, Isle of Wight Bay

WATER FRONT CONDO is a condo in Isle of Wight Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About WATER FRONT CONDO

WATER FRONT CONDO is a condo in Isle of Wight Bay, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,864.

From$178/night
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Bayview Bliss at Bridge Point 225 - Isle of Wight Bay, MD

Bayview Bliss at Bridge Point 225

Apartment, Isle of Wight Bay

Bayview Bliss at Bridge Point 225 is a apartment in Isle of Wight Bay, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Bayview Bliss at Bridge Point 225

Bayview Bliss at Bridge Point 225 is a apartment in Isle of Wight Bay, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,909.

From$184/night
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Renovated 3br/2ba townhouse- Groups welcome, Breezy Point 202 - Isle of Wight Bay, MD

Renovated 3br/2ba townhouse- Groups welcome, Breezy Point 202

Holiday Home, Isle of Wight Bay

Renovated 3br/2ba townhouse- Groups welcome, Breezy Point 202 is a holiday home in Isle of Wight Bay, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Renovated 3br/2ba townhouse- Groups welcome, Breezy Point 202

Renovated 3br/2ba townhouse- Groups welcome, Breezy Point 202 is a holiday home in Isle of Wight Bay, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,418.

From$204/night
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