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Winter Rentals

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15 properties were found meeting your search criteria.

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35 Bramblewood Drive - Website
Winter rental rate: $1261.00 per month. Basic cable/internet and trash included in price. Price is based on 4 month minimum rental. Security deposit required. Utilities are additional.This home offers 1800 Sq.Ft. with 4 bedrooms and 2 bathrooms. It is located on a wooded lot in Ocean Pines. The home is furnished with gas heat and deck. Bed sizes are 2 Queens and 4 twins.
        
Location: Ocean Pines - Wooded

Property Type: Single Family Home

Sleeps: 8   Bedrooms: 4

Beds: 2 Q's, 4 T's

Baths: 2  

Pets: No   Parking Spots: 3

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53 Moonraker Non-Group Rental
PROPERTY IS AVAILABLE FOR WINTER RENTAL AT $1300.00 PER MONTH PLUS UTILITIES. CALL OUR OFFICE FOR DETAILS. 1100 Sq. Ft. This 3 Bedroom, 2 Bath Rancher is fully and beautifully furnished, right down to decorative knick-knacks and dinner and glassware. Central Air and Heat Pump, Screened Porch and Deck, Shed. All furnishings must remain in home. Attic not available to tenant.
        
Location: Ocean Pines - Wooded

Property Type: Single Family Home

Sleeps: 6   Bedrooms: 3

Beds: K, 4 Twins, Trundle

Baths: 2  

Pets: No   Parking Spots: 3

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Ahoy 204, 137th st - Non Group Rental
WINTER RENTAL PRICE: $600.00. UTILITIES ADDITIONAL-ASK AGENT. SECURITY DEPOSIT IS REQUIRED. Very nice, 1 bedroom condo conveniently located to the beach. Enjoy quite uptown atmosphere of Ocean City. Unit features fully equipped kitchen, washer/dryer, Wall a/cs, 2 TVs, WIFI, private balcony with side ocean views. Linens, towels, paper products and soaps are not provided. Property is within walking distance to restaurants, shopping, Thunder Lagoon water park, miniature golf courses, movie theater.
        
Location: Ocean City-Ocean Block

Property Type: Condo

Sleeps: 4   Bedrooms: 1

Beds: Queen+queen sofa

Baths: 1  

Pets: No   Parking Spots: 1

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Birdnest By The Bay-Non Group Rental
Enjoy this brightly decorated 3 bedroom and 2 bathroom home with huge 20 x 14 foot screen porch. Cook for the family outside on the patio with the gas grill or gather the family inside and enjoy the central air conditioning.. Nicely equipped single family home located on a WOODED LOT in Ocean Pines. Relax with the family in the open area floor plan, or take in the fresh air with an evening meal on the screen porch. Hardwood floors in the living room/dining room/kitchen area and granite counter tops in the kitchen. Room for the family with one King, one Queen, 2 sets of Bunk beds, and a Quee...more info
        
Location: Ocean Pines - Wooded

Property Type: Single Family Home

Sleeps: 10   Bedrooms: 3

Beds: K, Q, 4 Twins, QSS

Baths: 2  

Pets: No   Parking Spots: 4

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D'Oshenest-Non Group Rental
Newly painted in 2016, newer outdoor bar stools and table, and newer outdoor ping pong table! Bright, cheery and meticulously maintained home sure to please and make your vacation comfortable and memorable. The home offers 3 bedroom with an additional large bonus room upstairs. Fully furnished and tastefully decorated, D'Oshenest amenities include screened porch, whirlpool tub, flat screen tv's, wi-fi, bikes, outdoor furniture and hammock. Iindoor shuffleboard, games, books, gas grill, outdoor ping pong table, and much more. Make D'Oshenest your vacation destination. GAS FIRE PIT IS NOT FOR TE...more info
        
Location: Ocean Pines - Wooded

Property Type: Single Family Home

Sleeps: 8   Bedrooms: 3

Beds: 2 Queens, 2 twins, QSS

Baths: 2   Half: 1 

Pets: No   Parking Spots: 4

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Easy Does It-Non Group Rental
Winter retnal rate: $2000.00. basic cable/internet and trash included in price.Price is based on a 4 month minimum rental.Security depsoit is required. Utilites are additional.  This home is located in the Glen Riddle community, which offers, golf, tennis courts, outdoor pool, and dining. This property offers ample space for the whole family. Larger home that can sleep up to 16 people. Boasts 5 bedrooms, 4 full bathrooms, and 1 half bathroom. Have a family movie night in the living room, or read your favorite book in the sitting room while the kids play in the upstairs loft area. Enjoy the wea...more info
        
Location: Glen Riddle

Property Type: Single Family Home

Sleeps: 16   Bedrooms: 5

Beds: 3Q, 5T, F, Bunk, see decrip

Baths: 4   Half: 1 

Pets: No   Parking Spots: 4

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Grayson Home- NON Group Rental
Winter rental rate: $1300.00. Basic cable/internet and trash included in price. Price is based on 4 month minimum rental. Security depsoit required.  Utilities are additional.   This cozy rental home in Ocean Pines would be a wonderful vacation home to make family memories! Near Ocean City, Maryland, this home offers 3 bedrooms and 2 bathrooms with deck. Enjoy an outside meal on the side deck or relax inside with a book. With living room and family room there is enough space for all. Wrap around couch allows for the whole family to enjoy a movie night. Open kitchen area for all your cooking ne...more info
        
Location: Ocean Pines - Wooded

Property Type: Single Family Home

Sleeps: 9   Bedrooms: 3

Beds: K, Q, PYR, QSS

Baths: 2  

Pets: Yes   Parking Spots: 4

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Hoops Coop Unit C 74th St, Non Group Rental
WINTER RENTAL PRICE: $850.00. PRICE BASED ON 5 MONTH MINIMUM RENTAL. UTILITIES ADDITIONAL-ASK AGENT. SECURITY DEPOSIT IS REQUIRED. Spectacular views of the Atlantic ocean from the living room, master bedroom and large balcony. Direct Ocean front building. FullyPANORAMIC BAY VIEW from the balcony of this 2 bedroom, 1 bath condo. Completely remodeled in 2016. Located in desirable mid town. Close to BJ's, Rope Walk, Hooked, Hobbit and many more. Just 2 1/2 blocks to the beach. Whatever you enjoy, be it a quiet cup of coffee in the morning or a cocktail in the afternoon, or just an afternoon with ...more info
        
Location: Ocean City-Bayfront

Property Type: Condo

Sleeps: 6   Bedrooms: 2

Beds: Q,PB, QSS

Baths: 1  

Pets: No   Parking Spots: 1

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Meile Home - Non group rental
Winter rental rate: $1350.00. Basic cable/internet and trash included in price. Price is based on 4 month minimum rental. Security deposit required. Utilities are additional. Enjoy this spacious waterfront property located in Ocean Pines. Bring the boat, take a mid day fishing trip, and then dock at the house upon your return. Complete with a 2nd floor in-law-quarters that boasts a separate kitchen, living room, bedroom, and bathroom for extended family room. The home has 4 bedrooms and 3 bathrooms with a huge kitchen to gather for family meals. The florida room offers views of the canal and d...more info
        
Location: Ocean Pines - Canal Front

Property Type: Single Family Home

Sleeps: 12   Bedrooms: 4

Beds: 3 Q's, 2 T's, 4 QSS

Baths: 3  

Pets: No   Parking Spots: 4

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No Wake Zone - Non Group Rental
Take the elevator up to this lovely third floor condo and enjoy an elevated view of the nearby marina. Featuring 2 bedrooms and 2 bathrooms, this condo is just a short walk to the Ocean Pines Yacht Club and the community pool. For a day at the beach, a free parking pass is provided to the Ocean Pines Beach Club located in Ocean City. There is no fee to access the beach or the cafe. After a long day, kick back in the condo and enjoy the comforts of home. Or, head over to The Cove for a nice family dinner. WiFi and cable are provided. Bed sizes include: 1 King, 2 Twins, and a FSS. 2 TV's and 1 D...more info
        
Location: Ocean Pines - Water Views

Property Type: Condo

Sleeps: 6   Bedrooms: 2

Beds: K, 2T, FSS

Baths: 2  

Pets: No   Parking Spots: 2

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Seas the Day 1, 78th St. Ocean Block
Pet Friendly!! One dog only. Great for large reunions. 2 units will accommodate up to 24 people. Located in mid-town, on the ocean side, just a few feet to the beach. The property is conveniently located to BJ's on the Water, Bayside Skillet, and beachwear stores. This unit features a fully equipped kitchen, TV, large deck with some views of the ocean and the bay. Within 200 feet to the beach. Linens and towels are provided for full week reservations only. UNIT RENTS ON A SATURDAY - SATURDAY BASIS DURING PRIME TIME. Mini-weeks and weekends are accepted in off season. ALL JUNE RENTALS HAVE A ...more info
        
Location: Ocean City-Ocean Block

Property Type: Condo

Sleeps: 10   Bedrooms: 3

Beds: Q, DD, DD, D-sofa

Baths: 2  

Pets: No   Parking Spots: 2

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Seas the Day 2, 78th St.
Pet Friendly, one dog only Check-in 3 p.m. - check out 10 a.m. Check in location is 8202 Coastal Hwy, Ocean City, MD 21842 For arrivals after 5 p.m. please call before 5 p.m. to make late check-in arrangements. Linens and towels are provided for full week (7 nights) reservations only. Great for large reunions. 2 units will accommodate up to 24 people. Located in mid-town, on the ocean side, just a few feet to the beach. The property is conveniently located to BJ's on the Water, Bayside Skillet, and beachwear stores. This unit features a fully equipped kitchen, TV, large deck with some views o...more info
        
Location: Ocean City-Ocean Block

Property Type: Condo

Sleeps: 10   Bedrooms: 3

Beds: Q, DD, DD, D-sofa

Baths: 2  

Pets: No   Parking Spots: 2

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Shuldes Home
Winter rental rate: $2000.00. Basic cable/internet and trash included in price. Security deposit required. Price based on 4 month minimum rental. Utilities are additional.   This 3699 square foot, 6 bedroom, 3.5 bathroom home, offers room for the whole family. Kitchen boasts tiled flooring, granite counter tops, and stainless steel appliances. Separate dining area off of the living room, and eat in kitchen will full views of the water. Large 2nd floor deck that wraps around from the kitchen area to the living room, and extends towards the water. Two master bedroom suites with attached tiled ba...more info
        
Location: Ocean Pines - Canal Front

Property Type: Single Family Home

Sleeps: 12   Bedrooms: 6

Beds: K, 2Q,4T,2Bunks

Baths: 3   Half: 1 

Pets: No   Parking Spots: 4

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Tiki 1 - 83rd St. Ocean Block
Rent 1 unit or both. This ocean-block duplex is located only 50 yards from a guarded beach in mid-town Ocean City, MD. The location is extremely convenient - it's only steps away from the beach, so returning home for lunch is a breeze. There is an outside enclosed shower so that everyone can rinse off salt and sand. You will also find plenty of ground-level storage for your beach items. All of the comforts of home await you at Tiki: a well-equipped kitchen, full-sized washer and dryer, TV with VCR and DVD players. Walking distance to Rope Walk and Hooked restaurants, Dunkin Donuts, Fat Daddy'...more info
        
Location: Ocean City-Ocean Block

Property Type: Apartment

Sleeps: 8   Bedrooms: 3

Beds: D, TT, TT, Q-sofa

Baths: 1  

Pets: No   Parking Spots: 2

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Tiki 2 - 83rd St. Ocean Block
Rent 1 unit or both. This ocean-block duplex is located only 50 yards from a guarded beach in mid-town Ocean City, MD. The location is extremely convenient - it's only steps away from the beach, so returning home for lunch is a breeze. There is an outside enclosed shower so that everyone can rinse off salt and sand. You will also find plenty of ground-level storage for your beach items. All of the comforts of home await you at Tiki: a well-equipped kitchen, full-sized washer and dryer, TV with VCR and DVD players. Walking distance to Rope Walk and Hooked restaurants, Dunkin Donuts, Fat Daddy'...more info
        
Location: Ocean City-Ocean Block

Property Type: Apartment

Sleeps: 8   Bedrooms: 3

Beds: D, D,TT, SOFA

Baths: 1  

Pets: No   Parking Spots: 2
HILEMAN REAL ESTATE
Toll Free: 800-337-7368   |   Local: 410-208-9200   |   Fax: 410-208-9562
8202 Coastal Hwy., Ocean City, MD 21842  |  Office Number: (800) 337-7368
11065 Cathell Rd., Berlin, MD 21811  |  Office Number: (800) 337-7368