Vacation rentals in Grasonville

A waterfront building is raised on stilts, featuring a white exterior and a metal roof. The structure is highlighted by a wraparound porch and multiple windows. Surrounding it, a wooden dock extends into the water, with posts visible along the shore.

4.93 out of 5 average rating, 278 reviews

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets Parties & 14 max guests. Book Today!

Guesthouse in Stevensville

5 out of 5 average rating, 34 reviews

Private | Near BayBridge | Wedding Venue Proximity

Welcome to your Kent Island getaway! This thoughtfully decorated, private guesthouse is minutes from the Bay Bridge, offering the perfect retreat for families, couples, or friends. Skip the hotel and relax in a fully stocked home with plenty of space, a large backyard for activities, and cozy touches throughout. Whether you're here for a wedding, visiting the Naval Academy or DC, or simply exploring the Eastern Shore, you'll love the comfort, convenience, and local charm this home has to offer.

Apartment in Stevensville

A spacious backyard features a sizable in-ground pool surrounded by lounge chairs and a shaded canopy. Lush greenery provides a serene backdrop, while a colorful mat adds a decorative touch to the outdoor space. Floating devices are visible on the water's surface.

4.98 out of 5 average rating, 278 reviews

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.

4.89 out of 5 average rating, 205 reviews

A fire pit is situated in the foreground, flames dancing within its sleek, modern design. The backdrop features the expansive Chester River, with calm waters reflecting a clear sky and distant shoreline, providing a serene setting for relaxation.

Apartment 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.

4.99 out of 5 average rating, 178 reviews

A view from the rooftop deck showcases a serene body of water, framed by a modern bridge above. Two vibrant red umbrellas provide shade on the deck, while boats navigate the waterway, illustrating the lively maritime activity in the Kent Narrows.

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!

4.95 out of 5 average rating, 273 reviews

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

Guest suite in Chestertown

Two comfortable adirondack chairs are positioned on a wooden deck, facing a scenic view of a tidal creek surrounded by trees. A small black table sits between the chairs, offering a space for refreshments while enjoying the natural surroundings.

4.99 out of 5 average rating, 225 reviews

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.

4.99 out of 5 average rating, 115 reviews

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.99 out of 5 average rating, 605 reviews

A glass table holds a coffee cup and a paper bag from a local café, alongside a pastry and a muffin. Two white Adirondack chairs frame the scene, set against a backdrop of lush greenery and a garden statue.

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.

4.86 out of 5 average rating, 57 reviews

Kent Island Waterfront Home

Enjoy a delightful stay at our waterfront 2 bedroom house for your Kent Island trip. The unit is equipped with a full kitchen including cookware and essentials for all your cooking needs, microwave, Wifi, TV, security cameras. Blankets, pillows, linens and bath towels. The house is a Self-Check-in, perfectly situated near all the local Kent Island Restaurants, Shops, Wedding Venues, Public beach access, wineries and so many more attractions to enjoy. We look forward to hosting you!

5 out of 5 average rating, 59 reviews

Home in Grasonville

Bay Breeze - 3BR Waterfront Chester River Retreat

Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing getaway. Take in breathtaking sunsets from the double-decker porches overlooking the Chester River, unwind by the fire pit, host a crab feast or enjoy a BBQ on the private dock. Ideally located just 5-10 minutes from Kent Island’s top restaurants and wedding venues, with a community playground, pavilion, and boat ramp just steps away. Your waterfont escape awaits!

Guesthouse in Stevensville

4.99 out of 5 average rating, 279 reviews

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.

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Popular amenities for Grasonville vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Grasonville

5 out of 5 average rating, 15 reviews

Aerial view of a multi-level custom home surrounded by lush greenery. The spacious deck features several outdoor seating options. A pathway leads to the backyard, showcasing well-maintained landscaping and access to waterfront views.

Home in Chester

Spacious waterfront home private pier dog-friendly

KarenRating, 5 stars1 week ago

The accommodations did not disappoint! Fabulous view, fun choices to take advantage of on the water, great neighborhood and local seafood restaurants! Our family gathering was memorable as a result of this venue! Will be sure to return!

Houseboat in Stevensville

4.94 out of 5 average rating, 53 reviews

Chesapeake Houseboat Getaway

RomaRating, 5 stars1 month ago

I loved Julia’s Arc. First time I Airbnb’d in a houseboat; won’t be my last. I loved this experience! Julia’s was inviting, comfortable, well appointed. I enjoyed sitting on the upper deck but even sitting inside with the blinds up and the windows open afforded the sounds of the water while enjoying the view of the marina and boats. I wish I had more time here to explore more. This was exactly what I needed for some time alone.

Guesthouse in Grasonville

A charming outdoor seating area is set beneath a large tree, featuring a white wrought iron bench and a small table adorned with a potted flowering plant. The surrounding green lawn offers a tranquil and inviting space for relaxation.

4.9 out of 5 average rating, 230 reviews

Eastern Shore Charm on Winchester Creek

CharlieRating, 5 stars1 week ago

Great host! Friendly and made us feel at home. Had tons of complimentary snacks and drinks, and gave us free muffins that were amazing.

5 out of 5 average rating, 46 reviews

Away at the Bay: New Home on the Chesapeake Bay!

PaigeRating, 5 stars3 weeks ago

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

4.93 out of 5 average rating, 42 reviews

A charming two-story house features a gabled roof and a welcoming entrance surrounded by vibrant greenery. Tall evergreen shrubs line the path, and a wooden porch with white railings invites guests to explore the home. Natural light filters through the windows, highlighting the house's character.

Cottage in Centreville

Captain’s Quarters - Unique home on Corsica River!

LoriRating, 5 stars10 months ago

An incredibly peaceful setting, we enjoyed time on the main floor deck watching the wild life and river! A perfect place to reflect with a good cup of coffee in hand!

4.93 out of 5 average rating, 44 reviews

The open kitchen features wooden ceilings with exposed beams and ample natural light from large windows. A gas stove, refrigerator, and microwave are visible. A small dining table with four chairs is placed nearby, enhancing the inviting atmosphere of the space.

Guesthouse in Rock Hall

Carriage House

LouiseRating, 5 stars2 weeks ago

The carriage house was perfect for our 3 night weekend. It felt like a beautiful treehouse, and we loved sitting on the porch under the magnificent magnolia trees, listening to the birds and the beautiful music from the neighboring church. The apartment had everything we needed, and we were able to dine at 3 of the area restaurants, which were all wonderful. Hope to stay there again next year. Susan is the perfect host. Many thanks to Susan for sharing her private hideaway.