Holiday rentals in Pittsville

5 out of 5 average rating, 106 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.

4.89 out of 5 average rating, 284 reviews

Tiny home in Snow Hill

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

4.97 out of 5 average rating, 586 reviews

Flat 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)

4.95 out of 5 average rating, 123 reviews

Loft in Salisbury

Tree Top Loft

Studio apartment is located on a wooded lot in a quiet neighborhood within 4 miles of Salisbury University & Downtown! Off street parking at entrance patio & a flight of stairs leads up to the apartment, which includes a queen size bed, full kitchen with full size refrigerator, 4 burner electric stove, full size washer and dryer. Bathroom includes shower, toilet and vanity, perfect for a week or weekend stay! We are located near Ocean City, Maryland, Assateague National Seashore.

4.99 out of 5 average rating, 204 reviews

Salisbury Cottage

Relax in a quiet part of Salisbury in this cozy, 3 bedroom, 2 full bath home. A farmhouse feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island. One mile from Tidal Health PRMC and a half block away from Salisbury University.

4.95 out of 5 average rating, 119 reviews

Bus in Frankford

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

4.99 out of 5 average rating, 202 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!

Superhost

Guest suite in Crisfield

4.75 out of 5 average rating, 211 reviews

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.

4.85 out of 5 average rating, 136 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.

4.98 out of 5 average rating, 107 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.

4.9 out of 5 average rating, 135 reviews

Ocean Side Condo-Steps From The Beach!

Enjoy a relaxing getaway at our Ocean Side condo. Just steps from the beach, our condo is centrally located on 44th St. Within walking distance of the Convention Center, Seacrets, 44th St. Taphouse, Mini Golf, and many other restaurants and shopping. Fully furnished, updated, clean, and modern. Washer/Dryer in unit.

4.98 out of 5 average rating, 102 reviews

Jamaica Couples Getaway

Newly renovated downtown studio unit perfect for a couple (or single traveler). Located right next to jolly rogers water park and within walking distance to several bars and restaurants. Condo is an efficiency so a smaller space than a one bedroom condo but very cute and cozy.

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Other great holiday rentals in Pittsville

4.75 out of 5 average rating, 8 reviews

New Bright & Cozy Townhouse

LeslieRating, 5 stars10 months ago

Very nice place to stay! 40 mins from Ocean City, MD. Great place to stay for USSSA Nationals Tournament in Salisbury. Close to shopping centers and lots of restaurants. Townhouse was clean and in a quiet neighborhood. Host was very responsive-would definitely stay here again.

4.67 out of 5 average rating, 208 reviews

Hidden Gem (North OC) - 2 mins to Beach

AltonRating, 5 stars3 days ago

Ryan’s spot was an absolute gem! Super clean, stylish, and had everything we needed for a smooth and comfortable stay. The location was perfect—close to everything, but still quiet enough to relax. Ryan was super responsive and made check-in a breeze. You can tell he really cares about the guest experience. Would 100% stay here again and recommend it to anyone looking for a hassle-free getaway!

4.9 out of 5 average rating, 83 reviews

Stella

KeishaRating, 5 stars3 weeks ago

Just lovely...are the best words to describe this home!! Kristin's place is very well decorated and is spotless. My son had a baseball tournament in the area, so we only stayed one night, but it was perfect. Hotel rates in the Salisbury area are absolutely ridiculous, so we were so glad to have found Kristin's place. Note that there is only one shower, but this home is perfect for a small group. Highly recommend!

4.93 out of 5 average rating, 57 reviews

Flat in Salisbury

Cozy, quiet…. Serenity Awaits

EthanRating, 5 stars6 months ago

Very clean and easy to maintain place. A little smaller than the pictures look but it’s more than enough room for 1-2 people. Definitely recommend if you’re in the Salisbury area.

Campervan/Motorhome in Salisbury

4.9 out of 5 average rating, 10 reviews

Private motorhome in Salisbury

AndreaRating, 5 stars1 week ago

Very nice little place! The deck and outside fire pit was very inviting, we loved having a fenced in area for the dog and kids! Our host was very responsive, we came back from the beach one day and the power/AC was out, and within 15 minutes of messaging him, everything was back in order. The camper is a little tight inside for 2 adults and 2 kids, but was perfect for us because the weather was great and we were just inside the camper to sleep, and the outside area was lovely. Thanks for a great stay!

Tiny home in Millsboro

4.8 out of 5 average rating, 128 reviews

Farm Cottage - POOL - 30 Min to BEACH

LisaRating, 5 stars1 week ago

Renee’s place was wonderful! She was very friendly. She showed us her tiny house that she just finished and took our grandson out to the chickens to feed them and get eggs. We enjoyed swimming in her pool. It’s like staying at a friend’s place. We loved our stay here and would highly recommend.

4.96 out of 5 average rating, 77 reviews

Gorgeous New Beachfront! King Bed, Direct Sea View

ConnorRating, 5 stars6 days ago

Fun place. Extremely easy to get to the beach. Very clean and had a GREAT coffee nook. Everything was clean and as described. Host was very responsive and we would recommend to anyone!