Vacation rentals in Pittsville

The Burley Bungalow

Located in the “coolest small town in America,” this cozy getaway offers unparalleled access to the charms of Berlin’s Main Street and its many restaurants, shops, and galleries. A mere five-minute walk from Burley Oak Brewing Company, this one bedroom accommodation is also conveniently local to the beaches at Ocean City & Assateague Island. A private entrance and plenty of on-site conveniences ensure your stay in beautiful Berlin will be homey & delightful. Worcester County, MD License #3506

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1‑bedroom studio 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 with king bed and full pull‑out couch. Workspace, fast WiFi, kitchenette, private laundry. Safe neighborhood, off‑street parking, well‑lit walkways. Private backyard patio with 6' fence. Stylish, super clean and comfortable. Sorry....no 3rd‑party bookings, pets, parties, indoor smoking or cooking.

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.

The Garden at Clayton House

This newly renovated home in the heart of Dagsboro is a peaceful garden getaway. Visitors are perfectly situated to enjoy the world-class Delaware Botanic Gardens and are minutes to Millville, Ocean View and the DE & MD beaches. From Clayton house you can walk to charming antique & gift shops, a diner style restaurant, a cafe with coffee and ice cream, a toy store, a quilt shop, a barber shop and beauty parlor, a movie theater and a beautiful park. Come experience the charm of Dagsboro.

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!

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

Bethany Bay. Sleeps 4. AC, Pool, Ground Floor

Unit 6302 at Bethany Bay is a 2 BR, 2 Bath, ground floor unit with panoramic views of the waterways and Indian River Bay. Sleeps 4. Free parking. Fully equipped kitchen, AC, fireplace, community outdoor pool, jogging/hiking path, 9 hole golf course. NON-SMOKING UNIT. Enjoy dinner and drinks on the enclosed rear porch and take in the view. 5 miles to Bethany Beach, 12 miles to Ocean City, 17 miles to Rehoboth Beach. I will allow one dog and the pet fee is $200.

Forest Grove Retreat

Quaint two bedroom house situated on a large country lot, fire pit, car port. Centrally located between Salisbury and the Beaches... Ocean City and Assateague Island. Distance to Ocean City and Assateague is about 20-30 minutes. The scenic route to Assateague will take you through Berlin, MD. A beautiful town with lots of restaurants and shopping. The second bedroom is off of the main bedroom, has privacy. We have WiFi! Pets Allowed

Historic On Main Street Apartment (B) Berlin, MD

Cozy - Historic Downtown Main Street 1 BDR, 1 BTH Apartment In Berlin, MD This Upstairs Apartment is right on Main Street - with great views of main street from the living room windows. The front door takes you right out onto the street! The building this apartment sits in, was built in 1896. Gives the apartment uniqueness and character! King bed in bedroom, small futon in living room, 1 twin inflatable mattress in the closet. Sleeps 4 max.

Private Cottage * 1 bedroom+loft * Rehoboth Beach

Welcome to Salt Box Cottage! I am thrilled to share my dream vacation home with you! You will be a short distance away from all that Rehoboth, Dewey and Lowes Beaches have to offer. You will have access to 2 bicycles and beach chairs during your stay. When you are not out and about you will have access to the entire cottage, which is well appointed with a full kitchen, towels, linens, laundry room across the way and 2 free parking spots.

Secluded Waterfront 15mi to Beach•Kayaks•Fast WiFi

Casa Blue Heron is a 2,254 ft² (209 m²) custom home offering stunning water views, a firepit, and serene seclusion at our 3-bedroom waterfront sanctuary by Chincoteague Bay and near Assateague, Berlin, Ocean City, Snow Hill and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature... Wish I had booked an extra day!" Add us to your wish list by clicking the❤️in the upper-right corner.