We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Grasonville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Grasonville

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Rental unit in Stevensville

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Rental unit in Grasonville

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to some restaurants.

Houseboat in Grasonville

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Guest suite in Arnold

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!

Home in Grasonville

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Casa particular in Chestertown

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Guest suite in Stevensville

Kent Island Haven - A Waterfront Getaway

Located across the bay from Annapolis, Kent Island Haven is a convenient and beautiful alternative to a hotel. Near shopping, nature areas, and walking trails; as well as the fine restaurants and water-oriented features of the Eastern Shore. Convenient to Baltimore, DC, Easton and St. Michaels. This 600 square foot 1 BR/1 BA in-law apartment has a private entrance and full kitchen. Watch the ships and ospreys from the living room. Enjoy the waterside hammock, pier, patio, and garden.

Guesthouse in Easton

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Guest suite in Chestertown

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Rental unit in Chester

Cozy Waterfront Apartment Chester, MD

*We live on the property* Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. Plus an easy to assemble blow up air mattress to sleep an additional two. WiFi included. Private porch to sit & enjoy beautiful water views!

Guesthouse in Stevensville

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Guesthouse in Grasonville

Eastern Shore Charm on Winchester Creek

My place is close to restaurants and dining and great views. You’ll love my place because of the comfy bed, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers; sorry no kids. Need at least three days notice to book guest house, I like to be here when you arrive, thus schedule my social activities around bookings.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Grasonville vacation rentals

Free parking on premises

Air conditioning

Stay near Grasonville's top sights

The Jetty46 locals recommend

Chesapeake Bay Environmental Center20 locals recommend

Denny's3 locals recommend

Other great vacation rentals in Grasonville

Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

Home in Stevensville

The Kent Island House

Cottage in Saint Michaels

La Casita on Harris Creek, St. Michaels

Home in Annapolis

Cape St Claire waterfront getaway

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Guesthouse in Queenstown

Waterfront Getaway

Guesthouse in Wye Mills

Adorable Lake Front 1BR Cottage-fully furnished!

Guesthouse in Stevensville

Chesapeake Cottage

Quick stats about vacation rentals in Grasonville

Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.3K reviews

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Grasonville?
Yes! Work meets play with ease at over 10 vacation rentals in Grasonville featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Grasonville have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Grasonville. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Grasonville?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Grasonville?
Grasonville has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Grasonville have free parking?
Absolutely! We offer over 10 house rentals with free parking in Grasonville. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Grasonville?
Experience the best of Grasonville with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Grasonville have wifi?
Absolutely! We offer over 10 house rentals with wifi in Grasonville. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Grasonville have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Grasonville. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore