Private suite holiday rentals in Delmarva Peninsula

Stunning private waterfront suite

Welcome to your cozy getaway with stunning water views from every room! This sweet 2-bedroom, 1-bath suite boasts a private entrance, a living room, and a cute kitchenette. Nestled in a peaceful, family-friendly neighborhood, you'll have year-round access to swimming pools, a golf course, tennis courts, a Yacht club, and lovely parks nearby. Only a quick 10-minute drive lands you on the sandy beaches and lively Boardwalk of Ocean City. Park in the driveway and step into your own private escape!

The Osprey Nest: Rappahannock Riverfront Suite

Sunny, private 2nd floor suite at the river's edge with panoramic views of the Rappahannock and surrounding farmland. Fiery sunsets, sunrises, starry skies, soaring eagles, and ospreys await. Swim, fish, explore the waterways by kayak, or bike in this tranquil, rural setting. Mornings on the balcony, with the songbirds is a treat, and relaxing on the riverfront "treehouse" deck, is sublime. Restaurants, historic sites, hiking, fossil hunting, wineries, antiques & more are a short car ride away.

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 pull‑out couch. Workspace, fast WiFi, kitchenette (no cooking), 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.

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate a portion of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

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.

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Treehouse Studio - kayaks included

Escape to the Treehouse in beautiful Urbanna! Our studio apartment is located in Fort Nonsense, a 3-story home with panoramic views of Urbanna Creek and the Rappahannock River. The Treehouse at Fort Nonsense is a peaceful getaway perfect for couples or solo travelers. **New in 2026** There is a new, queen-sized fold-out bed to replace the sofa bed and address negative feedback. This apartment is a unique space to work with, but we strive to provide a comfortable and budget friendly stay.

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

The Guest of Honor: Fenced Smart Home w/Hot Tub

This stylish ground-level only private space (Not a basement) is only 23 min from DC (30-35 min to downtown DC) 5 min from Andrew's Airforce Base, 15 min from the National Harbor & walking distance to Cosca Park. Cosca Park Amenities Include Baseball Fields, Outdoor Tennis Courts, Tennis Bubble, Walking Trail/Nature Trail, RestRooms, Playground, Skateboard Park, Paddle Boats on the Lake, Picnic Tables & Shelters, Nature Center, RV/Campground & parking lots.

Quiet setting on private pond among the wildlife

Enjoy a quiet, private setting just 3 miles from the Bethany Beach boardwalk. Nestled across from the Assawoman Wildlife Refuge, you can relax in a spacious home away from home. Plenty of room for the kids to play outside while you relax on the dock overlooking the pond. Guests have access to the second floor of the home which includes a full size kitchen, 3 bedrooms and living room that all have Smart TVs. Plenty of parking for you and guests.

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.