Vacation rentals in Grasonville

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.

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

Screened Porch | Near Bay Bridge & USNA | Big Yard

Welcome to your perfect Kent Island getaway! This newly listed home features a tastefully decorated 3-bedroom home, accommodating up to 8 guests. Enjoy the screened-in porch, wrap-around deck with rocking chairs, and large backyard with outdoor dining for any fun activity. You will be minutes from the Bay Bridge and several of Kent Island's premier venues and restaurants, making this home ideal for wedding guests, an Annapolis/DC trip, or if you're simply looking to explore the Eastern Shore.

Heron Roost

Heron Roost is a centrally-located waterfront apartment on a private gated lot with a heated pool. The view from your sun deck is the best on the property with spectacular sunrise and moonrise. We are conveniently located about one mile from the Chesapeake Bay Beach Club and twenty minutes from the US Naval Academy in Annapolis. There are numerous excellent restaurants and bars nearby and the towns of Easton and St Michael’s are close. Please come and enjoy our peaceful and unique property.

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

Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walking distance to a small community beach. Enjoy kayaking, biking, and crabbing on Kent Island right out of your front door. Perfect for multiple families (especially with younger kids) or attending one of the many wedding venues! 15 minutes off the Bay Bridge and easy access to groceries stores, outlet shopping, and restaurants. Come stay with us and enjoy being away at the bay!

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

*NewHotTub*LuxuryCoastal*CloseToWeddingVenues

Come enjoy the coastal lifestyle of the Chesapeake Bay with friends & family! Relax every evening on the back deck watching the beautiful cattails & sun set into the Bay every night. This spacious home can sleep 10 guests and is furnished with all new high-end furnishings, linens, 100% cotton sheets, luxury towels, & a fully stocked kitchen! We are very close to all the wedding venues on Kent Island plus 1 mile of all the restaurants,marinas,& live music. No additional visitors/guests allowed.

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.

Bayview Bungalow - Water view, EV charging station

One level living with a view across the Chesapeake Bay of the most amazing sunsets over the Annapolis skyline. Enjoy the large fully stocked kitchen, spacious bedrooms, claw foot tub & separate shower, deck, bbq grill, fire pit, & yard. Take the bikes on the local trails, nap on the hammock, play corn hole, take the beach chairs/toys to the private neighborhood beach, go to one of the many excellent restaurants, visit historic Stevensville, take a trip to Annapolis or DC, & so much more!

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

Relax in this Stylish Coastal-Country Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups! We're 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 or Parties & 14 max guests (8 max adults). Book Today!

Island Life 2 2024 Remodeled Home

Relax in this brilliant 3-bedroom, 2 bath coastal-country home in Stevensville. Remodeled and refurnished completely in 2024 with 2 king beds and 2 queen beds, this adorable property offers a cozy retreat for our guests. A great place to call homebase while you're away and enjoy Kent Island's best restaurants, dock bars and wedding venues. Nestled on a 22 acres of private waterfront estate. Stroll on the pier or catch some crabs. Bring your boat! We hope you enjoy your stay.