Vacation rentals in Pittsville

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Top-rated vacation rentals in Pittsville

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Top guest favorite

Guest suite in Delmar

5 out of 5 average rating, 106 reviews

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.

Top guest favorite

Home in Selbyville

4.95 out of 5 average rating, 115 reviews

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

Guest favorite

Tiny home in Snow Hill

4.89 out of 5 average rating, 284 reviews

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.

Top guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 586 reviews

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)

Guest favorite

Loft in Salisbury

4.95 out of 5 average rating, 123 reviews

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.

Top guest favorite

Home in Salisbury

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.

Top guest favorite

Guest suite in Berlin

4.99 out of 5 average rating, 202 reviews

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.

Guest favorite

Tiny home in Salisbury

4.85 out of 5 average rating, 136 reviews

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.

Top guest favorite

Home in Pittsville

4.98 out of 5 average rating, 107 reviews

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.

Guest favorite

Condo in Ocean City

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.

Top guest favorite

Condo in Ocean City

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 vacation rentals in Pittsville

Guest favorite

Home in Salisbury

4.9 out of 5 average rating, 31 reviews

Newly Renovated 3 Bedroom Home

AngieRating, 5 stars1 week ago

I cant say enough good things about this home! I felt right at home the moment I opened the front door. The kitchen was super clean and large dining table was perfect for a family meal. The bedrooms were perfect size and the beds/pillows very comfortable. The huge fenced in yard was great for the kids to run and play while we sat on the deck. Honestly, cant say enough good things - felt very safe and cozy, just like home.

Guest favorite

Home in Salisbury

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.

Guest favorite

Apartment in Snow Hill

4.93 out of 5 average rating, 14 reviews

The Top of Downtown Snow Hill

HeatherRating, 5 stars3 weeks ago

Blair's condo was the perfect spot for our weekend trip. The condo was beautiful with all the necessities. It also has a good location, and is centrally located to Snow Hill shops and dining as well as a short drive from Assateague and Ocean City. We highly recommend this stay!

Condo in Ocean City

4.67 out of 5 average rating, 208 reviews

Hidden Gem (North OC) - 2 mins to Beach

AltonRating, 5 stars2 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!

Guest favorite

Apartment in Salisbury

4.93 out of 5 average rating, 57 reviews

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.

Camper/RV in Salisbury

4.9 out of 5 average rating, 10 reviews

Autocaravana privada en Salisbury

AndreaRating, 5 stars6 days 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.

Top guest favorite