Vacation rentals in Romancoke

4.93 out of 5 average rating, 224 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! 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, Parties or Large Groups (11 max). Book Today!

Apartment in Stevensville

4.98 out of 5 average rating, 278 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.

4.99 out of 5 average rating, 176 reviews

Houseboat in Grasonville

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!

5 out of 5 average rating, 170 reviews

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

5 out of 5 average rating, 114 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

Guesthouse 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.

4.94 out of 5 average rating, 66 reviews

Modern Island Escape by the Bay

Welcome to Island Time! We think you are going to love it here! This home has just gone through a renovation completed in 2023. We went with the Island theme starting with our massive Kitchen Island, which serves as the hub of the house. Right off the kitchen is our back deck that spans the length of the house and over looks the paver patio, and fire pit below. We are centrally located to all the wedding venues, restaurants, and Bay Bridge access to Annapolis, DC, and beyond.

Guesthouse in Stevensville

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.

Superhost

5 out of 5 average rating, 4 reviews

Find your quiet at The Creek House on Kent Island

Welcome to the Creek House on Kent Island! This cozy home is situated directly on Tolson Creek, which leads out to the Chesapeake Bay. The location of the home is both peaceful and serene, but also located within 20 minutes of shopping, wedding venues, water view restaurants, and more. Enjoy evening walks in the peaceful neighborhood, and end with a view of the sunset over the Bay at one of the two small neighborhood look outs (one includes a beach!).

Guest suite in Saint Michaels

4.78 out of 5 average rating, 358 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

4.95 out of 5 average rating, 158 reviews

Cottage in Stevensville

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.

4.95 out of 5 average rating, 19 reviews

Bayou on the Bay

This exceptional bayfront retreat boasts breathtaking views and contemporary elegance, making it an ideal escape. Situated close to top-notch restaurants and the Naval Academy, guests can indulge in the picturesque bay vistas while unwinding in our luxurious jacuzzi. We look forward to welcoming you soon and invite you to inquire about our exclusive wedding packages.

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Other great vacation rentals in Romancoke

4.88 out of 5 average rating, 8 reviews

Waterfront Escape with Pool Nature Lover Paradise

AnaRating, 5 stars2 weeks ago

Hosted my intimate wedding at Nancy’s home and we had an amazing weekend! My family & closest friends loved the home, location, amenities & the coziness of the house. Perfect for a lil vacation with friends & family and very kid friendly. Absolutely loved my stay. Thanks for letting us stay at your place, view was incredible and so much space for a big group. Will definitely come back and recommend 100%

5 out of 5 average rating, 21 reviews

Chessie Cottage - Chesapeake Bay

CarolineRating, 5 stars1 month ago

We had the BEST time staying at this beautiful home this past weekend while we were in town for a wedding. The location is absolutely perfect for a peaceful weekend on the water and this house is a DREAM. Thank you so much for letting us stay at your incredible home!

Apartment in Stevensville

4.98 out of 5 average rating, 42 reviews

Relax Inn

ElizabethRating, 5 stars1 week ago

When they say Restful ... they meant it. It was so peaceful and a very nice neighborhood. We stayed for 4 nights and were able to go to all the beautiful towns and natural beauty around. Close to St. Michaels, Easton, Cambridge. Wonderful hosts. With out own deck next to a lovely water feature. The bed was king size and perfect! I would recommend this to anyone. We will be back. Thank you Tina and Tony! Bette and Lou

Guesthouse in Grasonville

4.9 out of 5 average rating, 230 reviews

Eastern Shore Charm on Winchester Creek

CharlieRating, 5 starstoday

Great host! Friendly and made us feel at home. Had tons of complimentary snacks and drinks, and gave us free muffins that were amazing.

4.81 out of 5 average rating, 89 reviews

Chesapeake Bay Water Front Home w/ Private Pier

JakeRating, 5 stars11 months ago

Jim's Bay house is great - incredible views, huge lawn, sizeable kitchen and living space. The master bedroom is enormous. Our group had a great time hanging on the lawn/deck and lounging around the multiple living rooms. The pier is nice for fishing (we didn't catch much), but I wouldn't recommend swimming or boating as it's very shallow. There is a small community beach two houses down (1 min walk) that is perfect for taking a dip on a hot day.

5 out of 5 average rating, 11 reviews

Home in Shady Side

The Wise Quack 2 - A Taste of the Chesapeake Bay!

ToddRating, 5 stars1 week ago

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.