Holiday rentals in Greenbackville

4.94 out of 5 average rating, 109 reviews

Home in Chincoteague

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayak on Oyster bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.81 out of 5 average rating, 147 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.

4.83 out of 5 average rating, 101 reviews

Cottage in Chincoteague

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Just a few miles from the Chincoteague National Wildlife Refuge & Assateague Beach. Ivy's Cottage offers a great in-town location that's close to shops, restaurants, waterfront park, & public fishing pier. This beautifully renovated, this Chincoteague Island Cottage Features: Lovely eat in kitchen, fully equipped w/ all amenities. Cozy living room w/ full sleeper sofa & recliner. Queen bedroom w/ adjacent full bathroom. Large front porch perfect for outdoor dining & park style charcoal grill!

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.

4.95 out of 5 average rating, 161 reviews

Cottage in Chincoteague

Summer's Sea Shanty on Chincoteague Island

Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

4.96 out of 5 average rating, 277 reviews

Apartment in Ocean City

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

4.99 out of 5 average rating, 90 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, 131 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, 212 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.

4.86 out of 5 average rating, 189 reviews

Flat in Chincoteague

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, 288 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.

4.98 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.

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Other great holiday rentals in Greenbackville

Home in Greenbackville

4.57 out of 5 average rating, 72 reviews

CAPTAINS COVE RESORT COMMUNITY

AbbyRating, 5 stars11 months ago

We stayed for a week at Kurt's place and had a blast. There was enough room that we were able to spread out but it was homey and served our group really well. The kitchen was stocked well and we were able to make a few nights of home made dinners at home. The kids especially loved all the toys that were around; they would come out with a new stuffed animal every day.

4.93 out of 5 average rating, 15 reviews

Flat in Snow Hill

The Top of Downtown Snow Hill

JeffRating, 5 stars2 days ago

Blair's apartment was spotless and very organized. Linens and sheets were immaculate. Great location for a quiant downtown stroll to Oak 110 or Elliot's Tavern. Great communication too. We will be back as we have family in the area.

Home in Horntown

4.9 out of 5 average rating, 10 reviews

Campfire Bliss at the Beach

AngelaRating, 5 stars9 months ago

This is a lovely little spot in Trails End. Everything was modern and beautiful. The kitchen was so spectacular I cooked on vacation. Would go back many times and probably will.

5 out of 5 average rating, 16 reviews

Home in Chincoteague

‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!

AfreenRating, 5 stars1 week ago

Beautiful and spacious place for our small family. Close to the beach and walkable to town. Cute ponies onsite too. Angie was very responsive and attentive!

4.98 out of 5 average rating, 41 reviews

Home in Greenbackville

Salty Paws - A Captain's Cove Vacation Home

HolgerRating, 5 stars10 months ago

Very enjoyable stay! The place is spacious, clean, well equipped, updated, and overall desirable. The neighborhood is quiet, walkable, and safe and the setting is lovely. The hosts were very responsive and helpful. We had particularly enjoyed the two kayaks (water access close by but check with the neighbor first as the launch site is his). Our Shiba loved the place as well as we were happy for the opportunity to bring her. After all, this was a rehab vac for her as she was recovering from a surgery ;-) But be aware that this is a residential neighborhood which means that things like ocean beach or places with a choice of restaurants are a drive away. Highly recommended.

5 out of 5 average rating, 11 reviews

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

KylieRating, 5 stars2 days ago

Can’t beat the views. It’s a quick drive into town. There is a great take out seafood restaurant!

4.94 out of 5 average rating, 90 reviews

Home in Chincoteague

Breeze on Inn

JimRating, 5 stars1 month ago

The house is spotless, clean and comfy. Host is friendly and responsive. The only bad thing was the clock in Livingroom always shows 6:21. But otherwise is perfect. I definitely will stay there again if I'm around the area.