Private suite holiday rentals near Chesapeake Bay

Baywatch North-Waterfront & Roaming Ponies

Calender open for super deals on weekly Summer rentals 2026. 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!

The Osprey Nest: Rappahannock Riverfront Suite

Sunny, private 2nd floor suite at the river's edge features panoramic views of the Rappahannock and surrounding farmland. Take in fiery sunsets, sunrises, starry skies, eagles, ospreys and more. Swim, fish, explore waterways by kayak, or bike in tranquil, rural surroundings. Morning coffee on the balcony with the songbirds is a treat, and the riverfront deck, surrounded by trees is sublime. Restaurants, historic sites, hiking, fossil hunting, wineries, antiques & more are a short car ride away.

Private guest suite in a newly remodeled home

We welcome you to a spacious and private basement apartment with its own entrance and self check-in. Get cozy with your guests in a space that has a bedroom with a king-size bed, an 85-inch smart TV, soft sectional , private toilet, bathroom and kitchenet, all in the same space. None of the amenities are shared. The fully-equipped kitchenet has everything you'll need to cook and warm your meals. Guest suite is the entire basement apartment which is a part of a bigger home where host lives.

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 options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

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.

Annapolis Garden Suite

Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

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.

Spacious 1bd in Trendy Capital Hill North

Stay in a historical row home ideally located in the Capitol Hill North neighborhood. Private entrance to this 1-bedroom (full bathroom and full kitchen) english basement apartment. Enjoy 750 sq ft of cozy, comfortable living space. Great for couples, business travelers, and vacationers. Convenient location with metro (Red line), Union Station, parks, Whole Foods, coffee shops, restaurants, and bars all within a 10-minute walk.

One Bedroom on Quiet Street in Heart of DC

Quiet and charming 1 bedroom English basement apartment with private entrance in hip Capitol Hill neighborhood. Easy walk to restaurants, cafes, Union Station, the Capitol, and other major DC attractions. Includes WiFi and TV with HBO and Netflix. Guests will have the entire apartment to themselves, which includes one bedroom and a living room area with small kitchenette, TV, kitchen table, and futon that folds down.

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

New Light suite, appartment comfortable living

Guest Suite apartment , on the ground floor. located on the back side of the house. The apartment includes 2 queen beds, 50 inch TV, kitchenette, living room dining area, and full bath. This apartment is fully private with a private entrance on the backside of the house. (no shared spaces). Please include total number of guests.