Vacation rentals in Whaleyville, MD

144 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals and Airbnb

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best vacation rentals and Airbnb offers in Whaleyville, MD

Bayside Resort --- 11029 Destination Drive - Whaleyville, MD

Bayside Resort --- 11029 Destination Drive

Holiday Home, Whaleyville

Bayside Resort --- 11029 Destination Drive is a holiday home in Whaleyville, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Bayside Resort --- 11029 Destination Drive

Bayside Resort --- 11029 Destination Drive is a holiday home in Whaleyville, with 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: pool, hot tub, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,450.

From$227/night
Show
Bayside Resort - 11444 West Sand Cove - Whaleyville, MD

Bayside Resort - 11444 West Sand Cove

Holiday Home, Whaleyville

Bayside Resort - 11444 West Sand Cove is a holiday home in Whaleyville, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Bayside Resort - 11444 West Sand Cove

Bayside Resort - 11444 West Sand Cove is a holiday home in Whaleyville, with 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: pool, hot tub, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,733.

From$261/night
Show
Strawberry Crossroads - Whaleyville, MD

Strawberry Crossroads

Cabin, Whaleyville

Strawberry Crossroads is a cabin in Whaleyville, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Strawberry Crossroads

Strawberry Crossroads is a cabin in Whaleyville, with pet-friendly 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: pet friendly, pets friendly, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,155.

From$147/night
Show
White Horse Park-spinnaker Lane 96 4 Bedroom Home - Whaleyville, MD

White Horse Park-spinnaker Lane 96 4 Bedroom Home

Holiday Home, Whaleyville

White Horse Park-spinnaker Lane 96 4 Bedroom Home is a holiday home in Whaleyville, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About White Horse Park-spinnaker Lane 96 4 Bedroom Home

White Horse Park-spinnaker Lane 96 4 Bedroom Home is a holiday home in Whaleyville, with pool 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: pool, free wifi, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,585.

From$176/night
Show

Vacation rentals with a pool in Whaleyville, MD

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

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. - Whaleyville, MD

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC.

Holiday Home, Whaleyville

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. is a holiday home in Whaleyville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC.

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. is a holiday home in Whaleyville, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,144.

From$163/night
Show
CUTE AND COZY IN OCEAN PINES - Whaleyville, MD

CUTE AND COZY IN OCEAN PINES

Holiday Home, Whaleyville

CUTE AND COZY IN OCEAN PINES is a holiday home in Whaleyville, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About CUTE AND COZY IN OCEAN PINES

CUTE AND COZY IN OCEAN PINES is a holiday home in Whaleyville, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,950.

From$279/night
Show
3-Bed, 2-Bath Home in Ocean Pines, MD – Just 15 Minutes from Ocean City Beaches - Whaleyville, MD

3-Bed, 2-Bath Home in Ocean Pines, MD – Just 15 Minutes from Ocean City Beaches

Holiday Home, Whaleyville

3-Bed, 2-Bath Home in Ocean Pines, MD – Just 15 Minutes from Ocean City Beaches is a holiday home in Whaleyville, with pool access, easy beach access, and kitchen access. This stay gives…

Read more

About 3-Bed, 2-Bath Home in Ocean Pines, MD – Just 15 Minutes from Ocean City Beaches

3-Bed, 2-Bath Home in Ocean Pines, MD – Just 15 Minutes from Ocean City Beaches is a holiday home in Whaleyville, 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 $1,980.

From$283/night
Show
8 Mi to Beach: Ocean Pines Home Near Marina & Golf - Whaleyville, MD

8 Mi to Beach: Ocean Pines Home Near Marina & Golf

Cottage, Whaleyville

8 Mi to Beach: Ocean Pines Home Near Marina & Golf is a cottage in Whaleyville, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About 8 Mi to Beach: Ocean Pines Home Near Marina & Golf

8 Mi to Beach: Ocean Pines Home Near Marina & Golf is a cottage in Whaleyville, 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 $2,904.

From$320/night
Show

Vacation rentals with parking in Whaleyville, MD

Find vacation rentals that make arriving by car easier.

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. - Whaleyville, MD

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC.

Holiday Home, Whaleyville

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. is a holiday home in Whaleyville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC.

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. is a holiday home in Whaleyville, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,387.

From$198/night
Show
Home in private gated community - Assateague Pointe/tons of fun amenities - Whaleyville, MD

Home in private gated community - Assateague Pointe/tons of fun amenities

Holiday Home, Whaleyville

Home in private gated community - Assateague Pointe/tons of fun amenities is a holiday home in Whaleyville, with pool access, parking, and kitchen access. This stay gives travelers a…

Read more

About Home in private gated community - Assateague Pointe/tons of fun amenities

Home in private gated community - Assateague Pointe/tons of fun amenities is a holiday home in Whaleyville, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,398.

From$200/night
Show
Beautiful Quiet Beach Home in the Pines Close to Everything - Whaleyville, MD

Beautiful Quiet Beach Home in the Pines Close to Everything

Holiday Home, Whaleyville

Beautiful Quiet Beach Home in the Pines Close to Everything is a holiday home in Whaleyville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

Read more

About Beautiful Quiet Beach Home in the Pines Close to Everything

Beautiful Quiet Beach Home in the Pines Close to Everything is a holiday home in Whaleyville, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,846.

From$264/night
Show
Covered Patio, Grill & Hammock: Frankford Home! - Whaleyville, MD

Covered Patio, Grill & Hammock: Frankford Home!

Holiday Home, Whaleyville

Covered Patio, Grill & Hammock: Frankford Home! is a holiday home in Whaleyville, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Covered Patio, Grill & Hammock: Frankford Home!

Covered Patio, Grill & Hammock: Frankford Home! is a holiday home in Whaleyville, with 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, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,842.

From$306/night
Show

Pet-friendly vacation rentals in Whaleyville, MD

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

5 Mins to the Beach, Pool,Tennis/Pickleball, Free Activities Inc. 18 Holes - Whaleyville, MD

5 Mins to the Beach, Pool,Tennis/Pickleball, Free Activities Inc. 18 Holes

Holiday Home, Whaleyville

5 Mins to the Beach, Pool,Tennis/Pickleball, Free Activities Inc. 18 Holes is a holiday home in Whaleyville, with pet-friendly space, pool access, and easy beach access. This stay gives…

Read more

About 5 Mins to the Beach, Pool,Tennis/Pickleball, Free Activities Inc. 18 Holes

5 Mins to the Beach, Pool,Tennis/Pickleball, Free Activities Inc. 18 Holes is a holiday home in Whaleyville, 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: pet friendly, pets friendly, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,075.

From$296/night
Show
Shore Point Cottages - Whaleyville, MD

Shore Point Cottages

Cottage, Whaleyville

Shore Point Cottages is a cottage in Whaleyville, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Shore Point Cottages

Shore Point Cottages is a cottage in Whaleyville, with pet-friendly space and pool 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,494.

From$303/night
Show
Downtown Berlin Home w Historic Charm Dog Friendly Home - Whaleyville, MD

Downtown Berlin Home w Historic Charm Dog Friendly Home

Holiday Home, Whaleyville

Downtown Berlin Home w Historic Charm Dog Friendly Home is a holiday home in Whaleyville, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Downtown Berlin Home w Historic Charm Dog Friendly Home

Downtown Berlin Home w Historic Charm Dog Friendly Home is a holiday home in Whaleyville, with pet-friendly 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,431.

From$347/night
Show
Nicely Updated Three Bedroom Home in Ocean Pines - Whaleyville, MD

Nicely Updated Three Bedroom Home in Ocean Pines

Holiday Home, Whaleyville

Nicely Updated Three Bedroom Home in Ocean Pines is a holiday home in Whaleyville, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

Read more

About Nicely Updated Three Bedroom Home in Ocean Pines

Nicely Updated Three Bedroom Home in Ocean Pines is a holiday home in Whaleyville, 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 $2,481.

From$354/night
Show

Vacation rentals with a kitchen in Whaleyville, MD

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

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. - Whaleyville, MD

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC.

Holiday Home, Whaleyville

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. is a holiday home in Whaleyville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC.

Assateague Pointe 2 br/1 ba 2 outdoor pools -in WOC. is a holiday home in Whaleyville, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,503.

From$215/night
Show
\"The Hive\"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath - Whaleyville, MD

\"The Hive\"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath

Holiday Home, Whaleyville

\"The Hive\"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath is a holiday home in Whaleyville, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About \"The Hive\"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath

\"The Hive\"-Downtown Berlin, 4 BR, Sleeps 8, 2 Bath is a holiday home in Whaleyville, with parking, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,300.

From$329/night
Show
Charming 3-bedroom house in wonderful and fascinating Berlin, MD. - Whaleyville, MD

Charming 3-bedroom house in wonderful and fascinating Berlin, MD.

Holiday Home, Whaleyville

Charming 3-bedroom house in wonderful and fascinating Berlin, MD. is a holiday home in Whaleyville, with parking, kitchen access, and room for a group. This stay gives travelers a…

Read more

About Charming 3-bedroom house in wonderful and fascinating Berlin, MD.

Charming 3-bedroom house in wonderful and fascinating Berlin, MD. is a holiday home in Whaleyville, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,385.

From$341/night
Show
Family Fun! Getaway w/ Pool & Marina in Berlin - Whaleyville, MD

Family Fun! Getaway w/ Pool & Marina in Berlin

Holiday Home, Whaleyville

Family Fun! Getaway w/ Pool & Marina in Berlin is a holiday home in Whaleyville, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Family Fun! Getaway w/ Pool & Marina in Berlin

Family Fun! Getaway w/ Pool & Marina in Berlin is a holiday home in Whaleyville, 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 $2,424.

From$346/night
Show

Family-friendly vacation rentals in Whaleyville, MD

Plan a trip with stays that give families more room to spread out.

Inn on Turville Cottage, Sleeps 4, waterfront - Whaleyville, MD

Inn on Turville Cottage, Sleeps 4, waterfront

Apartment, Whaleyville

Inn on Turville Cottage, Sleeps 4, waterfront is a apartment in Whaleyville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Inn on Turville Cottage, Sleeps 4, waterfront

Inn on Turville Cottage, Sleeps 4, waterfront is a apartment in Whaleyville, 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 $1,575.

From$225/night
Show
Inn on Turville Cottage, Sleeps 4, Waterfront - Whaleyville, MD

Inn on Turville Cottage, Sleeps 4, Waterfront

Apartment, Whaleyville

Inn on Turville Cottage, Sleeps 4, Waterfront is a apartment in Whaleyville, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Inn on Turville Cottage, Sleeps 4, Waterfront

Inn on Turville Cottage, Sleeps 4, Waterfront is a apartment in Whaleyville, 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 $1,596.

From$228/night
Show
Perfect Family Vacation House with quiet neighborhood but close to excitement. - Whaleyville, MD

Perfect Family Vacation House with quiet neighborhood but close to excitement.

Holiday Home, Whaleyville

Perfect Family Vacation House with quiet neighborhood but close to excitement. is a holiday home in Whaleyville, with pool access, kitchen access, and room for a group. This stay gives…

Read more

About Perfect Family Vacation House with quiet neighborhood but close to excitement.

Perfect Family Vacation House with quiet neighborhood but close to excitement. is a holiday home in Whaleyville, with pool 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, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,980.

From$283/night
Show
Pool & Marina: Family Home ~ 11 Mi to Ocean City - Whaleyville, MD

Pool & Marina: Family Home ~ 11 Mi to Ocean City

Cottage, Whaleyville

Pool & Marina: Family Home ~ 11 Mi to Ocean City is a cottage in Whaleyville, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Pool & Marina: Family Home ~ 11 Mi to Ocean City

Pool & Marina: Family Home ~ 11 Mi to Ocean City is a cottage in Whaleyville, 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 $2,722.

From$319/night
Show