Holiday houses in Girdletree

4.81 out of 5 average rating, 146 reviews

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

We're inside a lovely gated campground community with full amenities @ the Club House: Wi-Fi, pool, fishing n crabbing, boat ramp, laundry, and bath houses. The Bug-a-Boo is a lovely single dwelling home. It is ADA handicap accessible. There's an outdoor fire pit and space for camping. We are 20 miles from Chincoteague National Wildlife Refuge with miles of protected beaches. This is a peaceful place for soul searching & social distancing. We are also 42 mi from Assateague Is. Nat. Seashore.

4.89 out of 5 average rating, 283 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.

4.96 out of 5 average rating, 448 reviews

Townhouse in Ocean City

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

4.99 out of 5 average rating, 89 reviews

Loft in Pocomoke City

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

4.87 out of 5 average rating, 126 reviews

Houseboat in Snow Hill

"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.

4.75 out of 5 average rating, 209 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.

Apartment in Chincoteague

4.86 out of 5 average rating, 189 reviews

Sunset Haven Downtown

Broadband WIFI newly installed and dependable! This special place is located in the heart of historic downtown Chincoteague above a wine shop/jewelry boutique. Your backyard is a waterfront park with our famous Love Chairs! Watch the sunset from your waterfront window or deck. Walk to shopping, restaurants, and more! An apartment with old time charm and new polished adds to feel as modern as needed! Onsite Laundry- Linens provided

Guest suite in Chincoteague

4.98 out of 5 average rating, 287 reviews

Baywatch Upper-Waterfront & Roaming Ponies!

Discounted rates for weekly rentals Summer ‘25. Beautiful space in and out! Situated right on the bay with views of Assateague across the way, Chincoteague ponies are on premises. Coastal charm at its finest, there are 2 queen bedrooms and livingroom/breakfast room, all with a view. No full kitchen. Microwave, toaster, small fridge, stocked Keurig coffee and tea station and shared outdoor cooking area, sink and bbq grill.

4.84 out of 5 average rating, 134 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, 106 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.

4.98 out of 5 average rating, 281 reviews

Tiny home in Selbyville

Destination Location! Farm Animals, Tours, Beaches

✨Scratch tiny house living off your bucket list!✨ Wake up to the cheerful sounds of barnyard animals that surround this unique tiny house escape! The "Garden Hideaway" is thoughtfully curated to inspire joy and help you reconnect with the simpler things in life. Just a few minutes from the beach, this tiny home comfortably sleeps two (2) guests, with an option to add a third (3) for a small fee.

Guesthouse 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.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Girdletree holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Girdletree

4.67 out of 5 average rating, 268 reviews

Condo in Chincoteague

Le Petit Paradis-Waterfront, pet-friendly Studio

RachelRating, 5 stars1 week ago

This place is amazing! Beautiful views, very clean and surprisingly spacious! Super close to everything to do in chincoteague. Thank you for having us!

4.92 out of 5 average rating, 13 reviews

Apartment in Snow Hill

The Top of Downtown Snow Hill

HeatherRating, 5 stars2 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!

5 out of 5 average rating, 7 reviews

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

ChristinaRating, 5 stars1 week ago

We had an amazing stay at Melanie’s waterfront home! The location was absolutely perfect right on the water with stunning views and peaceful surroundings. We loved having access to the kayaks, grill, and outdoor furniture it made it easy to relax and enjoy the beautiful setting. The house was fully equipped with everything we needed for a comfortable stay, and the neighborhood was quiet with super friendly neighbors. Melanie was a fantastic host thoughtful, responsive, and even left us a list of local restaurant recommendations, which turned out to be excellent! This spot was exactly what we were looking for, and we’re already looking forward to coming back. Highly recommend!

Home in Girdletree

4.6 out of 5 average rating, 55 reviews

Private Home in Quiet Beach Country setting

AmberRating, 5 stars2 weeks ago

We really enjoyed our stay! The home was cozy and it was very easy to get to the beach and nearby restaurants. The neighbors’ house was much closer than you could tell in the photos, so allowing our dog to use the backyard off leash wasn’t as easy as we had hoped. Otherwise, we had a great trip and loved the screened in porch!

4.92 out of 5 average rating, 25 reviews

Home in Snow Hill

Koi House

JaneRating, 5 stars4 months ago

We have used the home previously for additional space for visiting family. Was convenient again.

Guesthouse in Chincoteague

4.97 out of 5 average rating, 87 reviews

Cozy Beach Cottage

PollyRating, 5 stars4 days ago

This was my second stay at Barbara’s spot in chincoteague and it was excellent! My husband, dog, and I had a fantastic time. Her place is absolutely perfect for exploring the area and conveniently located to everything. The space is super cozy and we loved returning here in the evenings. Being able to bring my dog with us is also a huge plus as he loved going on vacation too! :) thanks so much for everything Barbara! We hope to return soon!

4.88 out of 5 average rating, 113 reviews

Apartment in Newark

Relax at the Shorehouse

MorganRating, 5 stars5 days ago

Margo was very nice and checked in with my throughout the weekend. The house was just as described and very clean! It was perfect for the two days we were there.