Vacation rentals in Assawoman

4.94 out of 5 average rating, 489 reviews

Tiny home in Accomac

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

4.98 out of 5 average rating, 129 reviews

Cottage in Greenbush

Bell Farm Cottage LLC - quiet and peaceful

Cozy cottage located on a quiet backroad overlooking a wide open field & back deck provides warm & sunny space for relaxing or reading a book. The kitchen is fully equipped. BFC has a warm farm house feel w/ a touch of the beach. The bathroom has been updated to a more modern feel. Located only a few miles from both seaside and bayside boat ramps. A 7 minute drive to Onancock, Walmart, YMCA, shopping & many local shops for just the right souvenir. Wallops & Chincoteague are just a short drive.

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.

4.99 out of 5 average rating, 265 reviews

Farm stay in Onancock

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

4.96 out of 5 average rating, 449 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 :)

4.98 out of 5 average rating, 267 reviews

Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

Tiny home in Cape Charles

4.98 out of 5 average rating, 318 reviews

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

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, 211 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.

Guest suite in Chincoteague

4.94 out of 5 average rating, 317 reviews

Baywatch North-Waterfront & Roaming Ponies

Lovely space! 2 queen bdrm unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

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

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.

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Other great vacation rentals in Assawoman

4.9 out of 5 average rating, 50 reviews

Home in Chincoteague

Oysterhaven Cottage

AaronRating, 5 stars2 days ago

very good communication, some beach gear available at the house which we were happy to have. location is quiet and about 3/4 mile to shops and restaurants. bring bikes or scooters for this island.

4.95 out of 5 average rating, 21 reviews

Home in Chincoteague

Jay's Retreat

MorganRating, 5 stars2 days ago

We loved our stay! The home was perfect for our young family. The location was perfect. We woke up every morning to a beautiful view. The location is private, we felt safe with our kids and dog walking around and riding bikes as there was hardly any traffic. Community is peaceful and calm with easy connection to town. Everything in the house is clearly marked with instructions. Our boys loved the toys on the rainy days and it was so nice to not have to pack bikes. We made so many great family memories. A great place to stay!

4.96 out of 5 average rating, 77 reviews

Condo in Ocean City

Gorgeous New Beachfront! King Bed, Direct Sea View

ConnorRating, 5 stars6 days ago

Fun place. Extremely easy to get to the beach. Very clean and had a GREAT coffee nook. Everything was clean and as described. Host was very responsive and we would recommend to anyone!

5 out of 5 average rating, 16 reviews

Home in Atlantic

A Private Quiet Eastern Shore Estate

YameletRating, 5 stars3 weeks ago

Our family had such a fun and relaxing weekend getaway! The Airbnb was clean, cozy, and had everything we needed. The beach was just a short drive away, which made it easy to spend the day by the ocean and come back to unwind. It was the perfect little escape—we’re so glad we found this place!

5 out of 5 average rating, 7 reviews

Apartment in Onancock

Retro Relaxo

ThomasRating, 5 stars1 week ago

This place is a real gem - quiet neighborhood with a porch overlooking the water. Peaceful, comfortable, and a not-overdone retro atmosphere. We highly recommend for a place to stay while exploring the Eastern Shore.

4.93 out of 5 average rating, 14 reviews

Cottage in Chincoteague

Twinkle Twinkle Little Tarr Renovated Cottage!

MaryRating, 5 stars4 weeks ago

This cottage is located at the end of a dead-end street on the east side of the island, which faces the Chincoteague Wildlife Refuge. The location was VERY quiet and serene, the cottage is surrounded by tall grass so you have total privacy. It is very small island so you are within minutes drive to local restaurants and access to the Refuge . The cottage was extremely comfortable, very nice furnishings and decor. And, I have to say one of the more comfortable beds I've slept in. The bed could use some new pillows though, they were very soft and lumpy. My only criticism of my stay was the expectation of what was expected of us when left the cottage. Basically, we were asked to swipe the floors, take out all the trash, and strip the bed, way and put away all dishes, this is on top of paying a very hefty cleaning fee. While I realize there was still more cleaning involved, I've never been asked to do so much on top of paying the cleaning fee.