Holiday rentals in Princess Anne

4.97 out of 5 average rating, 353 reviews

Home in Fruitland

Johnna's House

Two story dwelling in a prime location on the Eastern Shore of Maryland. It is conveniently located 32 miles from Ocean City. It is equipped with central air and heat, a two car garage, WiFi and cable. It is centrally located and is within walking distance of eateries and Super Wal-Mart. Pharmacies are in close proximity. It is also in walking distance from the local college, Salisbury University. And is less than a 1/2 mile from Salisbury City Limits. The local mall is only a 10 minute drive.

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)

4.99 out of 5 average rating, 69 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.

4.93 out of 5 average rating, 15 reviews

Home in Princess Anne

Peaceful Home Away from Home

Take a break and unwind at this peaceful home...or take advantage of the convenience to outdoor Eastern Shore activities. Conveniently close to crabbing, boating and fishing, this home provides peace and quiet while steps away from the joys of country living. Whether you're in town for the Skipjack Races in Deal Island, MD or graduation at HBCU, UMES, we are close enough to "town" but yet far enough from the hustle and bustle of town living. Travel Healthcare Professionals are welcome.

4.93 out of 5 average rating, 15 reviews

Home in Princess Anne

countryside home in Princess Anne

Escape to tranquility at our private home in the serene countryside. Our spacious and comfortable three-bedroom, two-bathroom home provides ample space for families, couples, and groups of friends to relax and enjoy the outdoors. Relax in the cozy living area, cook a meal in the fully equipped kitchen, or enjoy an evening around the campfire. With comfortable bedrooms and a peaceful location, it's the ideal getaway for a relaxing break. Book now and experience the beauty of rural living!

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.

Farm stay in Princess Anne

4.94 out of 5 average rating, 98 reviews

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

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.

5 out of 5 average rating, 103 reviews

Loft in Hebron

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

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.

Guest house in Pocomoke City

4.95 out of 5 average rating, 145 reviews

2 Bedroom Apartment

Centrally located between Chincoteague Island and Ocean City, MD. This pet friendly two bedroom apartment which offers laundry and a spacious kitchen is only steps away from Shad Landing state park and Public Landing. This ground level guesthouse apartment is located 200 feet from our main house is on an over 12 acre partially wooded parcel. Plenty of privacy and room for boat trailer parking.

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Other great holiday rentals in Princess Anne

Cottage in Deal Island

4.64 out of 5 average rating, 236 reviews

Deal Island Bay Cottage - Maryland

AshRating, 5 stars1 week ago

Great location. Very rural, quiet neighborhood, very responsive host.

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.

4.85 out of 5 average rating, 131 reviews

Highbanks House

RobertRating, 5 stars2 weeks ago

We stayed here for the Eagleman 70.3 and found the HighBanks house exactly what we needed and wanted. A secluded property where our families could relax and enjoy some time together. Parisa send us the information we needed and was very accommodating to us. We enjoyed staying at the HighBanks house and would recommend to others as well.

5 out of 5 average rating, 44 reviews

Cabin in Westover

Chalet Style Home, private country setting

AprilRating, 5 stars4 months ago

I recently stayed at Crooked Elm and was thoroughly impressed. The place was impeccably clean, and the attention to detail was evident in every corner. The host's responsiveness was top-notch! One feature that stood out was the guest binder. It was incredibly detailed, providing clear instructions on everything from using the fireplaces to local attractions and dining recommendations. This made it easy to settle in and feel at home. It had everything we needed for a cozy stay! Overall, my stay at Crooked Elm was delightful, and I highly recommend it to anyone looking for a cozy, well-managed retreat.

4.99 out of 5 average rating, 71 reviews

Luxe Zen Retreat

CadeRating, 5 stars1 week ago

Came to stay for a wedding. Could tell the home was newly renovated and very clean. Great place to stay.

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!

4.94 out of 5 average rating, 48 reviews

Home in Quantico

Home in historic village of Whitehaven, Maryland.

SavannahRating, 5 stars3 weeks ago

We had such a great experience staying at White Haven, definitely a beautiful and peaceful retreat!