Holiday rentals in Stevensville

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!

4.98 out of 5 average rating, 278 reviews

Flat 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.

4.92 out of 5 average rating, 83 reviews

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.

5 out of 5 average rating, 49 reviews

Flat in Stevensville

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.

4.89 out of 5 average rating, 205 reviews

Flat 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.

Guest house in Stevensville

5 out of 5 average rating, 55 reviews

Chesapeake Cottage

VERY CLOSE to island wedding venues. Cottage is a private detached 1st floor dwelling and has off street parking. Queen bed & trundle with 2 single beds, sleeps 4. There's a full/stocked kitchen & bath, large TV, small dining table, Keurig & coffee pods. Wifi and streaming service's included. Easy access with keyless entry. Efficiency space. Smoke/Vape allowed on front porch only. Located near the Bay bridge and bike paths, Historic downtown, winery & restaurants. *Message with any questions.

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

Houseboat in Kent Narrows

4.97 out of 5 average rating, 152 reviews

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

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.

4.9 out of 5 average rating, 290 reviews

Guest house in Annapolis

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.

Superhost

Flat in Stevensville

5 out of 5 average rating, 3 reviews

Private Unit•King Bed•Parking•WeddingVenues&USNA

Why choose a hotel when you can stay at Romancoke Retreat? This ⦁NEW LISTING⦁ is conveniently located just minutes from the iconic Bay Bridge and many of Kent Island's scenic wedding venues. The home's cozy BACK UNIT features 1 king bed and 1 full bath, dedicated parking, a private entrance, and offers just about everything you would need for a comfortable stay. Whether attending a wedding or exploring the island, Romancoke Retreat is your ideal home base for your Kent Island getaway.

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!

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Other great holiday rentals in Stevensville

4.97 out of 5 average rating, 71 reviews

Cozy home with Screened Porch, Min from Weddings

GregRating, 5 stars1 month ago

Great little place. Convenient to the island and the venues

4.98 out of 5 average rating, 64 reviews

Barn in Queenstown

Waterfront Modern Guest Barn

ThinhRating, 5 stars2 weeks ago

What an incredible property. One of the most beautiful places I’ve stayed. My friends and I enjoyed every minute of our stay. The water views and the ability to walk down to the water for fishing and kayaking was amazing. We spent so much time in the great room just chatting and enjoying the space. The kitchen was a chef’s dream with ease of use and everything where it needed to be. We would definitely stay again in the future.

Guest house in Grasonville

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.

Superhost

Guest house in Stevensville

4.62 out of 5 average rating, 116 reviews

Kent Island Waterfront Cottage

KimRating, 5 stars2 months ago

We really enjoyed our stay at Glen’s place on Kent Island. The view was stunning. That was my favorite part, just sitting outside having coffee and enjoying that gorgeous water view in peace and tranquility. We started off with a little bit of a hiccup, but I truly appreciated their response and taking care of it quickly. Life isn’t always perfect, but it’s how you respond to those situations that make all the difference. We ultimately had a great stay and would definitely recommend this property to our friends

5 out of 5 average rating, 5 reviews

Bay Bliss House

IanRating, 5 stars6 days ago

Beautiful property and well maintained. Unique views and plenty to do when the weather is not so good. Great proximity to Annapolis and the Eastern Shore and plenty of great dining spots on the water.

4.95 out of 5 average rating, 95 reviews

Home in Chester

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars3 weeks ago

The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

5 out of 5 average rating, 15 reviews

Gable’s Landing on the River.

TylerRating, 5 stars9 months ago

Immaculate and perfect....look no further if you are searching for a house on Kent Island. We were in town for a wedding and this AirBnb was beyond ideal. Spotless and clean, tasteful decor, and waterfront. All exactly as advertised, but looks even more picturesque in person. We really enjoyed being waterfront on the dock enjoying the mornings and evenings in peace. Highly recommend - it was difficult to leave!