Vacation rentals 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 several restaurant

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.

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

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.

The Fitz Inn

Arrive by boat or car to our cozy 1 BD/1BA private 500 sq ft cottage! Enjoy wineries, restaurants, bars & waterfront activities & return to the peaceful Fitz Inn. Sip coffee at sunrise & wine at sunset on Cox Creek (Benton's Pleasure area). Ideal for 2 guests, but can accommodate 4. Listing has AIRBNB exemption from hosting animals, including service & emotional support ones (please see property description for more details). No smoking. Flexible reschedule option with $100 administrative fee.

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

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.

Cozy Retreat w/Private Beach Access

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtful interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, couples romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Chestertown Private cottage with NFL Sun Ticket

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in the windows. Kitchenette has extra large toaster oven, two burner hot plate, microwave, fridge, and Keurig/drip coffee makers. King bed with 100% cotton 1000 thread count linens and deluxe mattress, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

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.

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!

Relax on Kent Island in 4 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 4 Bedroom Home with a view of the Chesapeake Bay! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets or Parties & 11 max guests (8 max adults). Book Today!