Holiday rentals in Maryland

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Top-rated holiday rentals in Maryland

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Superhost

Apartment in Ocean City

4.88 out of 5 average rating, 90 reviews

Luxurious Oceanfront Retreat with Amazing Views!

This stunning recently renovated direct Oceanfront condo features a designer king-sized bedroom, a chef's kitchen, a sunny living area with a 65" 4K smart tv, and unobstructed beach and ocean views that can't be beaten! Every detail is designed to give guests a stylish and sophisticated place to relax while offering all of the upscale amenities you'd expect in a luxury vacation rental. Located on the Ocean City Beach with unobstructed Beach and Ocean Views! 13 Min Drive to Ocean City Boardwalk

Guest favourite

Apartment in Ocean City

4.91 out of 5 average rating, 44 reviews

OCMD family vacation rental 2BR, 2BA, Pool.

Top floor end unit with large (private) wrap around balcony giving views of the ocean and bay! (54th street Bayside, 1 block from the beach). This 2 bedroom/2 bath is nicely furnished and can accommodate 8 guests. The kitchen is fully equipped with full sized fridge, microwave, dishwasher, washer/dryer, whirlpool tub, central A/C, cable and wifi. Location is perfect for walking to restaurants, miniature golf, shops and nightlife. Rental includes: pool/Hot tub, fitness center,two parking spots.

Top guest favourite

Townhouse in McHenry

5 out of 5 average rating, 39 reviews

Our Lovely Lake Retreat

Spacious 3 bedroom, 2.5 bath townhome with gorgeous views of Deep Creek Lake and WISP ski slopes. The newly updated townhome sleeps 8 comfortably. You will enjoy the air conditioning, fully equipped kitchen & grill, wood burning fireplace and 4 smart TV's. 15 steps up to entrance. Neighborhood amenities: indoor community pool, picnic tables, dock and a beach/sand area (kids will love). Level lakefront access right across the street. Min age to rent 25. Max 3 cars. HOA rule: no trailers/campers.

Superhost

Home in Ocean City

4.78 out of 5 average rating, 23 reviews

The Oliver House

This property boasts breathtaking views of the Ocean City skyline and is nestled in a quiet neighborhood in West Ocean City. Bring your boat, paddle boards, kayaks and firewood for the most incredible vacation. Crabs and clams are plentiful and the kids can enjoy playing in the small beach area while splashing or swimming in the bay. Although you may never want to leave, it's a short drive to Ocean City's beaches and boardwalk, Assateague Island and the quaint must-see town of Berlin, Maryland.

Guest favourite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Apartment in Ocean City

4.94 out of 5 average rating, 176 reviews

Modern Oceanside 42nd st 2bed 2bath sleeper sofa

Gorgeous 2 bed, 2 bath 1st floor condo is on 42nd st. Ocean side! Newly renovated, modern and clean condo sleeps 8 (air mattress for 2)has everything you need to feel like you’re at home away from home! Beautifully decorated and complete with stainless steel appliances, fully equipped kitchen, WiFi, a color changing gas fireplace, 80” tv, and is furnished with linens and towels. Just steps to the beach, convention canter and walking distance to the bars such as Seacrets, Coconuts and Taphouse.

Guest favourite

Home in Swanton

4.94 out of 5 average rating, 18 reviews

Renovated Home with Dock, HotTub, Golf DogFriendly

Recently renovated, this beautiful home sits on a hillside in the Waterfront Greens community. Stunning views, privacy, great location, and many amenities make it the perfect choice. The new deck has plenty of seating & some of the best views around. Waterfront Greens offers a par 3 golf course, mini golf, tennis, lake access and the dock area. One of the best locations in the area for safely walking & riding bikes. Please note that there is a pet fee (for up to 2 dogs) of $200.

Guest favourite

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Superhost

Chalet in Oakland

4.91 out of 5 average rating, 128 reviews

Spectacular Chalet, Timroc II, close to lake, Wisp

ENJOY every season!! Short walk to the lake and dock! ! 15 minute drive to Ski Wisp! Fire pit, decks and screened in porch! Relax in the hot tub, enjoy family and/ or friends time and just get away from it all! 5 comfortable sized bdrms, each with large windows letting in natural daylight. First floor master, hardwood flooring throughout, many sliders for easy access. Finished bsmt with pool table, separate bdrm, full bath and laundry! DON'T SEE YOUR DATE, PLEASE CALL!

Guest favourite

Flat in Ocean City

4.8 out of 5 average rating, 5 reviews

Aventurra 406| Outdoor Pool| Balcony

This is an Ocean City Vacation Homes property Soak up the sun on the beautiful beaches when you stay in this bright and airy 3 bedroom condo for 8. This stylish condo is located on the fourth floor, so you can easily admire the breathtaking ocean sunrise view and the amazing bayside sunset view. Boasting 2 private parking spaces, a kitchen, and a wraparound balcony, a pool, this is the ultimate beach destination. Please not the cleaning fee includes sheets and towels.

Top guest favourite

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favourite

Apartment in Oakland

4.91 out of 5 average rating, 79 reviews

Top Notch Lake Getaway - Cozy in a plush resort

Complete remodel and upgrades in Nov 2022. Unique space and a great getaway; 2 separate sleeping areas. Spacious +BR w/loft nestled on the shores of Deep Creek Lake, professionally furnished w/onsite mgmt, King bed in private bedroom w/closet, Queen bed in loft area, propane fireplace, kitchenette with microwave & full size fridge, keurig, full bath lower level, vaulted ceilings and much more. Community fitness center. Please, 25yo to rent.