Private suite holiday rentals in Tuckahoe

Beloved Chateau (with Hot Tub)

The Beloved Chateau is a guest suite in a character house in Adamstown. You will relax in a hot tub, enjoy a firm and comfortable bed with a newly renovated, modern bathroom. Our 55-inch TV gives you access to your personal streaming accounts. Whether you like to hike, shop for antiques in town, or enjoy a restful evening in, it is perfect for couples searching for a restful overnight stay. The room is fully independent from the rest of our house. It has a private entrance with NO shared space.

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Lucy's Log Cabin Cottage in the Woods

Cozy guest suite attached to main house in log cabin village. Full kitchen, dining area, wood stove, comfy queen bed, walk-in closet, games, 100 movies. Walk-in shower & built-in seat. Laundry room with door to deck area, bistro tables, firepit. The vaulted living room has pull-out love seat for one sleeper, TV [ROKU, You Tube TV, HULU, Netflix, Amazon, Disney], Blu-Ray player and Google Nest Mini. Enjoy breakfast items like fresh eggs, juice, milk, bread, coffee, tea and our homemade pizzelle.

House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

Charming Fully Equipped Private Guest Suite Studio

Relax in a stylish guest suite studio in a quiet, safe neighborhood. Its private entrance and parking for 2 vehicles makes the cozy space all the better. Enjoy the full kitchen, work space, high speed internet (1200mbps), 50” TV, full bathroom, and more. Perfect for the business professional on-the-go, or getaway. Take a stroll through White Clay Creek Park with your furry friend. Just a short 5 minute drive from Main St.'s restaurants, local bars, and UD. Only 10 minutes from Christiana Mall.

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.

Historic Downtown Garden Oasis with Private Patio

Welcome to 108Annex — a one-bedroom guesthouse tucked into the courtyard of a historic 1890s home in Chestertown, Maryland. Whether you're here for a long weekend on the Eastern Shore, a quiet escape from the city, or one of Chestertown's celebrated events, this is the kind of place you'll want to come back to. Steps from the Chester River, High Street restaurants, and Washington College, with a private patio and beautiful garden setting to return to at the end of the day.

Spacious 2BR Suite, Quiet Retreat, Family-Friendly

Enjoy room to relax in our family friendly, two bed room in-law suite minutes from Chester County sights and easy highway access. -Spacious living -Fast Wi-Fi & smart TV—for movie nights -Fully equipped kitchen & laundry available—ideal for longer stays -Quiet bedrooms with hotel-quality linens -Superhosts with a personal touch Visiting family, sports travel, etc.—our home keeps you close to everything! Ready for a worry-free stay? Tap “Reserve” to secure your dates.

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

Private Suite -Jacuzzi and Fireplace

Take a break and unwind at this peaceful oasis. Featuring a jacuzzi tub,spa shower and in room fireplace. Enjoy beautiful sunsets and view of horses grazing in the pasture from your room. Perfect place to relax or reconnect with your spouse. This is in-law quarters connected to our home but has its own private entrance. Things to note-There’s no tv or kitchen. Wifi,microwave and mini fridge provided. My prayer is that our home can be a blessing to you in some way!

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 Stone House between the Streams

While staying here, you will get to drive over a little bridge and past a winding stream to get to our historic stone house where you will stay. The original structure was built in 1758. Out in the country with Amish neighbors all around, you will be delighted with the peaceful environment created by the little streams, rustic barn, and buggies going by on the road. The property use to be a winery with it's own vineyards. The house was where the vintner lived.