Vacation rentals in Pittsville

5 out of 5 average rating, 104 reviews

Guest suite in Delmar

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1 bedroom studio centered on a quiet street in historic Delmar, MD. Kylan Barn - 6 min. Venue 54 - 7 min. Downtown Salisbury - 15 min. SU - 20 min. OCMD - 45 min. Sleeps (4). Queen bed and full size pull-out couch. Workspace, fast WIFI, kitchenette, private laundry. Safe neighborhood, off-street parking, well lit walkways. Inviting backyard patio with 6' tall privacy fence all just for you. Stylish, super clean and comfortable. Sorry no pets or smoking.

4.97 out of 5 average rating, 578 reviews

Apartment in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

4.98 out of 5 average rating, 66 reviews

Guest suite in Salisbury

Havana Hideaway

Havana Hideaway offers a charming and unique retreat inspired by the vibrant culture of Cuba, capturing the essence of Havana through its decor and ambiance. As you climb the stairs to its entrance above the barn, you are treated to beautiful pastoral sights. Inside, you are greeted by colorful and tropical-inspired decor that immediately transports you to a Cuban paradise. After a day in town or neighboring beaches, you can return to your tropical retreat and unwind on the private balcony.

4.98 out of 5 average rating, 43 reviews

Tiny home in Parsonsburg

Cozy Cottage Hideaway

This memorable place is anything but ordinary. Our tiny cottage was designed for a peaceful retreat or romantic getaway. It has a full size bed and also a twin that is suitable for a younger child. Step outside to enjoy the peaceful surroundings on the front deck, you may even see some fox, deer, or other wild life roaming the area. There is also a campfire and picnic area on site. The location is just a short drive to local beaches. This little gem offers the best of both worlds.

4.91 out of 5 average rating, 35 reviews

Apartment in Salisbury

Studio Apt. Close to the Beach

Wake to the sounds of nature in this beautiful semi-private neighborhood. Quiet shaded streets offer running, walking and biking. Enjoy the waterfall shower after a long day or take a relaxing stroll. Premises are under security surveillance 24/7. Like the beach? Drive to several within 45 minutes including Assateague Island National Seashore with its wild horse population. Kayaking, bowling, golf, breweries, the Salisbury Zoo, and Minor League Baseball are just a few miles away.

4.91 out of 5 average rating, 23 reviews

Tiny home in Selbyville

Ranch Glamping! Jail Cell theme, Tours, Beaches

Howdy Partner! Dust off your boots and glamp at Cowtown Cabins, the beach area's newest ranch experience featuring a Wild West movie town in the making! The "Jail Cell" is a ONE-ROOM mini-glamping cabin that has a (2) guest maximum and will take you back to the time of stealing horses & shootouts. However, this slammer comes with one queen-sized bed along with WIFI, a smart TV, a mini fridge/ freezer, an electric kettle, a pod-style coffee maker, and year-round heating/ AC.

4.98 out of 5 average rating, 198 reviews

Guest suite in Berlin

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin,Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

4.75 out of 5 average rating, 206 reviews

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

4.84 out of 5 average rating, 133 reviews

Tiny home in Salisbury

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

5 out of 5 average rating, 19 reviews

Home in Willards

Quiet country getaway

Newly remodeled ranch house in the country with beautiful sunrise and sunset views and stargazing. Centrally located between Salisbury and Ocean City. Perfect for summer vacations, University visits, sports tournaments, boating and fishing. Ocean City and Assateague Island State and Federal Parks are less than a 30 minute drive as well as the bay, rivers and inlets. Close to small town shopping and restaurants.

4.98 out of 5 average rating, 105 reviews

Home in Pittsville

Wagon Wheel Cottage

Remodeled country farm house cottage that was built by our uncle in a quiet rural area surrounded by farm land. Other family members live all around us. It's located in the small town of Powellville, Md. It is 21 miles from Assateague, 20 miles from Ocean City, 12 miles from Berlin, 13 miles from Salisbury and 41 miles from Chincotegue VA. Sorry we do not allow pets as some guest have pet allergies.

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4.79 out of 5 average rating, 24 reviews

Home in Ocean View

5 Bedroom-Award Winning Bear Trap Golf Community

VirajRating, 5 stars3 months ago

We had a great time with friends and family over the weekend at your house. it was perfectly sized and spacious. The added advantage of having access to the clubhouse was a perfect arrangement for kids. Sharing a very few things that we think can be improved upon - a. Given the winters are off peak time for this beach town and the fact that outdoor amenities are not usable such as Tennis, Basketball and Pickleball courts, the clubhouse rate is steep. b. Having to carry our own linens is not that big an issue but does add more luggage. at least towels should have been provided. c. None of the toilets had any toiletries. It was clarified before the trip that toiletries will be provided so we were caught off guard. d. The powder room which is the only toilet in the first floor, did not have Trash Can. Otherwise, it was a good outing. There was something to do for everyone. We thoroughly enjoyed. Lynn was generous enough and allowed early check-in.

5 out of 5 average rating, 5 reviews

Home in Pocomoke City

Vacation home near the beaches

NelsonRating, 5 stars10 months ago

Amazing Getaway!! Plenty of indoor and outdoor space, comfortable beds and all around just a wonderful stay. Highly recommend anyone looking for a place to stay with plenty of room and don’t mind a small commute to Chincoteague.

4.82 out of 5 average rating, 164 reviews

Home in Georgetown

Maplewood - Simply Comfortable, Dog Friendly

AubreyRating, 5 stars1 day ago

was exactly what we were looking for while in town for a baseball tournament. quick drive to the beaches as well. would stay again.

4.9 out of 5 average rating, 49 reviews

Condo in Ocean City

OCMD family vacation rental 2BD2BA, Pool/Hot tub

PeytonRating, 5 stars1 week ago

Had a great time, awesome location and extremely clean!

4.98 out of 5 average rating, 59 reviews

Home in Chincoteague

Central Location- Walk to Dining & Entertainment!

DebbieRating, 5 stars1 week ago

Enjoyed a comfortable stay and Chip and Courtney’s home. It was clean and nicely decorated. Made us feel right at home. The kitchen was well stocked with everything needed for meal preparation. Especially loved the well stocked coffee bar. Beds were comfy and bathrooms were well stocked with amenities. Chip and Courtney also left us their park pass to use at a nearby wildlife refuge park that has a nice beach. Chip and Courtney, thank you so much for being great hosts!

4.93 out of 5 average rating, 104 reviews

Condo in Rehoboth Beach

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

DianaRating, 5 starstoday

We had a wonderful time at Timothy's Airbnb in Rehoboth. The location was amazing and the home was clean and comfortable. Our host was very friendly and responsive.

4.78 out of 5 average rating, 45 reviews

Home in Lewes

AlyciaRating, 5 stars7 months ago

Such a perfect mix of private and secluded but easy access to the beach. Loved the fire pit. Family had a great time, house had everything needed for the weekend.