Holiday rentals in Stevensville

4.93 out of 5 average rating, 277 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!

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.

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.

5 out of 5 average rating, 48 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.

Superhost

Flat in Grasonville

4.89 out of 5 average rating, 204 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.

5 out of 5 average rating, 38 reviews

Home in Chester

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.

5 out of 5 average rating, 54 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, 272 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, 151 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.

4.85 out of 5 average rating, 55 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!

4.99 out of 5 average rating, 278 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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Other great holiday rentals in Stevensville

5 out of 5 average rating, 28 reviews

1969 Brick Rancher - Kent Island

JackRating, 5 stars3 weeks ago

Great stay! Very homey and warm inside. TONS of natural light, updated bathroom and kitchen finishings, and comfy beds. Host was very responsive and flexible! Great place to stay

4.98 out of 5 average rating, 63 reviews

Barn in Queenstown

Waterfront Modern Guest Barn

ElaineRating, 5 stars1 month ago

Overall, I enjoyed the place. The barn was minimalistic and nice for photos. The best part was the waterfront view. The house was very clean and pretty kid friendly (a few high chairs included). The kitchen had the bare minimum to cook and grill with but I wouldn’t say it was fully stocked. I would say in general that we enjoyed our stay. The kayaks were wonderful.

Guest house in Grasonville

4.9 out of 5 average rating, 230 reviews

Eastern Shore Charm on Winchester Creek

CharlieRating, 5 stars2 days 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

4.62 out of 5 average rating, 116 reviews

Kent Island Waterfront Cottage

KimRating, 5 stars1 month 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, 4 reviews

Bay Bliss House

EthanRating, 5 stars2 weeks ago

The Bay Bliss House is a wonderful stay! We were in town for a wedding at the Chesapeake Bay Inn and this was the perfect location for us. It is less than 10 minutes away from plenty of restaurants and stores and the neighborhood is lovely/safe. Olga was an extremely kind and responsive host throughout. Her messages in advance of and during the stay were very clear and her replies were timely when needed. She left local recommendations and plenty of amenities within the house for our use. Finally, the house itself is fantastic. Although it was a little cold with the wind off the bay, we thoroughly enjoyed the back patio with the built in pool. The views from relaxing in the sunroom were our favorite part of the trip. I would highly recommend this house for any future travelers.

4.95 out of 5 average rating, 95 reviews

Home in Chester

Waterfront Farmhouse Meets Modern Luxury

TrishRating, 5 stars2 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, 74 reviews

Home in Chester

Chester Delight- Fireplace/Deck&Patio+fenced yard

JessicaRating, 5 stars2 days ago

Had a great stay here with a large group for a local wedding! Would absolutely recommend for anyone needing a comfy spot for multiple guests on the island.