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Vacation rentals in Grasonville

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Top-rated vacation rentals in Grasonville

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Home in Stevensville

4.93 out of 5 average rating, 243 reviews

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

Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home w/3 acres of outdoor living! Perfect for Families & sleeps 14. 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 or Large Groups (14 max.). Book Today!

Rental unit in Stevensville

4.98 out of 5 average rating, 273 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.

Rental unit in Grasonville

4.89 out of 5 average rating, 195 reviews

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

4.99 out of 5 average rating, 149 reviews

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!

Home in Grasonville

4.95 out of 5 average rating, 256 reviews

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

Home in Stevensville

5 out of 5 average rating, 124 reviews

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Travel just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered patio on main level and 12' x 52' three season room on the upper level.

Home in Stevensville

5 out of 5 average rating, 103 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.

Guesthouse in Annapolis

4.9 out of 5 average rating, 250 reviews

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.

Guesthouse in Easton

4.99 out of 5 average rating, 579 reviews

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.

Guesthouse in Stevensville

5 out of 5 average rating, 250 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.

Cottage in Stevensville

4.95 out of 5 average rating, 151 reviews

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, & bike trails.

Rental unit in Chester

4.97 out of 5 average rating, 260 reviews

Cozy Waterfront Apartment Chester, MD

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 enjoy water view!

Vacation rentals for every style

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Homes

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Popular amenities for Grasonville vacation rentals

Free parking on premises

Air conditioning

Stay near Grasonville's top sights

Bridges Restaurant47 locals recommend

The Jetty46 locals recommend

Queenstown Premium Outlets41 locals recommend

Fisherman's Inn Restaurant27 locals recommend

Chesapeake Bay Environmental Center20 locals recommend

Hunter's Crabs & Seafood Market4 locals recommend

Other great vacation rentals in Grasonville

Guesthouse in Stevensville

5 out of 5 average rating, 45 reviews

Chesapeake Cottage

Home in Stevensville

4.96 out of 5 average rating, 23 reviews

Spacious4BR home with waterviews

Home in Stevensville

4.91 out of 5 average rating, 76 reviews

Cheerful & Spacious Shore Life Beauty!

Home in Greensboro

4.96 out of 5 average rating, 76 reviews

Cozy 2 bedroom home on wooded private lane

Cottage in Grasonville

4.88 out of 5 average rating, 60 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

Home in Stevensville

5 out of 5 average rating, 14 reviews

Gable’s Landing on the River.

Home in Stevensville

5 out of 5 average rating, 38 reviews

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

Home in Chester

5 out of 5 average rating, 63 reviews

Chester Delight- Fireplace/Deck&Patio+fenced yard

Quick stats about vacation rentals in Grasonville

Total rentals
20 properties
Total number of reviews
1.5K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

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 air conditioning, over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, 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.

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