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Vacation Homes in Ocean Pines

Find the vacation homes that appeal to you the most

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The best vacation homes in Ocean Pines

Check out our selection of great vacation homes in Ocean Pines

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Shore Point Cottages

Ocean City (Near Ocean Pines)

Offering a seasonal outdoor swimming pool, Shore Point Cottages offers accommodations in Ocean City. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

B
BRYANT
From
Canada
The grounds were very clean. Our cottage was a home away from home.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 538 reviews
Price from
$123.99
1 night, 2 adults
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Spacious 3-Bedroom, 3-Bathroom Condo in Ocean City with Beach and Bay Views

Ocean City (Near Ocean Pines)

Spacious 3-Bedroom, 3-Bathroom Condo in Ocean City with Beach and Bay Views offers accommodations in Ocean City, a few steps from Ocean City Beach and 1.3 miles from Roland E.

M
Matthew
From
United States
Very well kept, clean and close to the beach
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 6 reviews
Price from
$550
1 night, 2 adults
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Stunning Studio with community pool just steps to Beach and Boardwalk!

Ocean City (Near Ocean Pines)

Just a 2-minute walk from Ocean City Beach and 0.7 miles from Roland E. Powell Convention Center & Visitors Info Center, Stunning Studio with community pool just steps to Beach and Boardwalk!

J
JILL
From
United States
Conveniently located to where we wanted to go
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 5 reviews
Price from
$270
1 night, 2 adults
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PARADISE AT SUNSET ISLAND

Ocean City (Near Ocean Pines)

A 17-minute walk from Ocean City Beach in Ocean City, PARADISE AT SUNSET ISLAND offers accommodations with access to a hot tub.

K
Kimberly
From
United States
The room was clean and pretty.
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 5 reviews
Price from
$812.25
1 night, 2 adults
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BEACH HAVEN Dog friendly farmette Great for 2 couples

Berlin (Near Ocean Pines)

Offering a garden, BEACH HAVEN Dog friendly farmette Great for 2 couples offers accommodations in Berlin. This property offers access to a terrace and free private parking.

J
Jasmaine
From
United States
It very comfortable and gave the feeling of being at home.
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 14 reviews
Price from
$268.30
1 night, 2 adults
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Cozy Coastal Condo

Millsboro (Near Ocean Pines)

Cozy Coastal Condo offers accommodations in Millsboro, 18 miles from Thunder Lagoon Waterpark and 19 miles from Casino at Ocean Downs.

N
Nina
From
United States
Beautiful, comfortable property that felt like home.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 41 reviews
Price from
$375
1 night, 2 adults
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Pool, Trail Access! Dog-Friendly Ocean Pines Haven

Ocean Pines

Pool, Trail Access! Dog-Friendly Ocean Pines Haven offers accommodations in Ocean Pines, 8 miles from Jolly Roger at the Pier and 8 miles from Ocean City Boardwalk.

D
Danielle
From
United States
Beautiful home and beautiful area. Beautiful wooded area from master bedroom. Very clean. Would definitely be renting again!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
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9 Mi to Beach! Family Getaway in Ocean Pines

Ocean Pines

9 Mi to Beach! Family Getaway in Ocean Pines offers accommodations in Ocean Pines, 3.4 miles from Casino at Ocean Downs and 6.3 miles from Grand Prix Amusements.

H
Hayden Tarbox
From
United States
I really like the location of this property. it was quite and peaceful.
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 6 reviews
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Trinity Place Treasure

Ocean Pines

Trinity Place Treasure offers accommodations in Ocean Pines, 3.2 miles from Casino at Ocean Downs and 6.1 miles from Grand Prix Amusements.

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 5 reviews
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Coral Shells

Ocean Pines

Coral Shells offers accommodations in Ocean Pines, 3.9 miles from Casino at Ocean Downs and 6.8 miles from Grand Prix Amusements.

M
Molly
From
United States
It was clean and comfortable. We enjoyed coming back to this place at the end of the day.
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 9 reviews
Check availability
All vacation homes in Ocean Pines

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Ocean Pines and surrounding area in the past month

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Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews

Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Ocean Pines

Popular with guests booking vacation homes in Ocean Pines

Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Popular with guests booking vacation homes in Ocean Pines

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 6 reviews

Popular with guests booking vacation homes in Ocean Pines

Vacation Homes with swimming pools in Ocean Pines and nearby

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Scored out of 10, guest rating 7.0
Good - What previous guests thought, 2 reviews

5 Whitecap is located in Ocean Pines, just 4.5 miles from Casino at Ocean Downs and 7.4 miles from Grand Prix Amusements.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Drawbridge Rd 38 is located in Ocean Pines, just 4.4 miles from Casino at Ocean Downs and 7.3 miles from Grand Prix Amusements. The vacation home features an outdoor pool and free Wifi.

Heron Hideaway Canal-Front 3-Bedroom Home in Ocean Pines, MD, Near Ocean City Beaches is located in Berlin, just 4.7 miles from Casino at Ocean Downs and 7.6 miles from Grand Prix Amusements.

Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 5 reviews

Dove Lane 8 is located in Ocean Pines, just 9 miles from Roland E. Powell Convention Center & Visitors Info Center and 9.4 miles from Jolly Roger at the Pier.

Battersea on the Canal offers accommodations in Ocean Pines, 7.8 miles from Baja Amusements and 9 miles from Roland E. Powell Convention Center & Visitors Info Center.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

Featuring a casino, Teal Haven features accommodations in Ocean Pines. This property offers access to a patio, free private parking, and free Wifi.

Waterfront Cottage w/ Private Dock in Ocean Pines! offers accommodations in Ocean Pines, 5.2 miles from Casino at Ocean Downs and 8.1 miles from Grand Prix Amusements.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

14 Clipper on the Bay is located in Ocean Pines, just 5.2 miles from Casino at Ocean Downs and 8.1 miles from Grand Prix Amusements.

Great access to the city center. Check these vacation homes in Ocean Pines and nearby

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Furnished Deck! Waterfront Ocean Pines Home is located in Ocean Pines, just 10 miles from Roland E. Powell Convention Center & Visitors Info Center and 10 miles from Jolly Roger at the Pier.

37 Moonraker Road is located in Ocean Pines, just 4 miles from Casino at Ocean Downs and 6.9 miles from Grand Prix Amusements.

The Nest

Ocean Pines
Central location
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

The Nest is located in Ocean Pines, just 4.1 miles from Casino at Ocean Downs and 7.1 miles from Grand Prix Amusements. This vacation home provides air-conditioned accommodations with free Wifi.

Seafarer 7

Ocean Pines
Central location
Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 8 reviews

Seafarer 7 offers accommodations in Ocean Pines, 3.8 miles from Casino at Ocean Downs and 6.8 miles from Grand Prix Amusements.

3.9 miles from Casino at Ocean Downs in Ocean Pines, 2 Mi to Golf: Hot Tub Hideaway in Ocean Pines provides accommodations with access to a hot tub and spa center.

22 Harpoon rd

Ocean Pines
Central location

22 Harpoon rd is located in Ocean Pines, just 4 miles from Casino at Ocean Downs and 6.9 miles from Grand Prix Amusements. This vacation home features an outdoor pool and complimentary Wifi.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

5.8 miles from Casino at Ocean Downs in Ocean Pines, Game Room! Waterfront Group Haven in Ocean Pines provides accommodations with access to a hot tub.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Patio, Pool Access! Coastal Ocean Pines Cottage is located in Ocean Pines, just 5.2 miles from Casino at Ocean Downs and 8.2 miles from Grand Prix Amusements.

Enjoy breakfast in Ocean Pines and nearby

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White Horse Park-Spinnaker Lane 96 home offers accommodations in Berlin, 10 miles from Roland E. Powell Convention Center & Visitors Info Center and 10 miles from Jolly Roger at the Pier.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Relaxing Family Getaway, Quiet Area Mins from OC offers accommodations in Berlin, 10 miles from Roland E. Powell Convention Center & Visitors Info Center and 10 miles from Jolly Roger at the Pier.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 5 reviews

Dog Friendly! Ocean Pines 'Crabby Cottage' offers accommodations in Berlin, 5.2 miles from Casino at Ocean Downs and 8.1 miles from Grand Prix Amusements.

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 4 reviews

3.8 miles from Casino at Ocean Downs in Berlin, 9 Mi to Ocean City Beaches: Retreat w/ Patio features accommodations with access to a spa center.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Pet-Friendly Ocean Pines Cottage Family-Friendly Retreat with Amenities is located in Berlin, just 2.8 miles from Casino at Ocean Downs and 5.7 miles from Grand Prix Amusements.

Waterfront Coastal Retreat on Ocean Pines Golf Course with Private Dock is located in Berlin, just 5.3 miles from Casino at Ocean Downs and 8.2 miles from Grand Prix Amusements.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 3 reviews

Spacious Ocean Pines Home Perfect for Family Gatherings is located in Berlin, just 3.6 miles from Casino at Ocean Downs and 6.5 miles from Grand Prix Amusements.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Beaconhill Road 68 offers accommodations in Ocean Pines, 8.4 miles from Roland E. Powell Convention Center & Visitors Info Center and 8.7 miles from Jolly Roger at the Pier.

Save money on vacation homes in Ocean Pines and nearby – budget options available

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Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 2 reviews

Charming 3-Bed Cabin, Near Ocean City & Assateague is located in Berlin, just 3.2 miles from Casino at Ocean Downs and 6.1 miles from Grand Prix Amusements.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Boat Dock! Waterfront Group Getaway in Ocean Pines offers accommodations in Ocean Pines, 8.5 miles from Grand Prix Amusements and 9.1 miles from Baja Amusements.

838 Ocean Parkway

Ocean Pines
Budget options available
Scored out of 10, guest rating 6.5
Pleasant - What previous guests thought, 2 reviews

838 Ocean Parkway offers accommodations in Ocean Pines, 2.8 miles from Casino at Ocean Downs and 5.8 miles from Grand Prix Amusements. This vacation home provides accommodations with a patio.

Lighthouse Seclusion

Ocean Pines
Budget options available

Lighthouse Seclusion is located in Ocean Pines, just 3.5 miles from Casino at Ocean Downs and 6.4 miles from Grand Prix Amusements.

Scored out of 10, guest rating 4.0
Disappointing - What previous guests thought, 1 review

8 Mi to Ocean City: Warm & Cozy 3BR Family Home is located in Ocean Pines, just 3.3 miles from Casino at Ocean Downs and 6.2 miles from Grand Prix Amusements.

Turtle Shores

Ocean Pines
Budget options available

Turtle Shores is located in Ocean Pines, just 5.7 miles from Grand Prix Amusements and 6.2 miles from Baja Amusements. The air-conditioned accommodation is 2.7 miles from Casino at Ocean Downs.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Pool Access, Deck & Grill: Ocean Pines Getaway is located in Ocean Pines, just 3.6 miles from Casino at Ocean Downs and 6.5 miles from Grand Prix Amusements.

Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 2 reviews

Poolside Fun & Beach Access in Ocean Pines! is located in Ocean Pines, just 5.1 miles from Casino at Ocean Downs and 8 miles from Grand Prix Amusements.

FAQ about vacation homes in Ocean Pines