Holiday houses in Kent Island Estates

4.96 out of 5 average rating, 408 reviews

Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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!

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.

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Apartment 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.

4.96 out of 5 average rating, 671 reviews

Guest suite in Arnold

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

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.

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

4.94 out of 5 average rating, 176 reviews

Guest suite in Arnold

Coastal Comfort Suite Near Annapolis, Hottub, EV

Hot tub is open for the season. Pool will be open May 12 through Labor Day weekend. Ideal for a couple's retreat, this king suite guest room has a massive bedroom with a seating area, mounted TV, and coffee bar with microwave/mini-fridge. An ensuite bathroom provides a luxurious shower with dual shower heads and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

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

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.

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.

Cottage in Saint Michaels

4.97 out of 5 average rating, 164 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

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Other great holiday rentals in Kent Island Estates

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.

4.97 out of 5 average rating, 34 reviews

Spacious4BR home with waterviews

GaryRating, 5 stars3 weeks ago

5 adults, 2 children under age 6 stayed at Courtney's home, which was just as described and pictured on the airbnb web page. Great location for our stay for wedding weekend; very comfortable furniture (sofas, chairs, beds; many amenities provided for guests; terrific well-stocked kitchen; very large screened-in porch w/ nice view of Chesapeake Bay and surroundings; spacious bedrooms; 4 full bathrooms; very clean when we arrived. I could go on .... Courtney is a very good communicator, and responded quickly to the few questions we really had. She is a great host and the house was terrific for our needs.

4.92 out of 5 average rating, 83 reviews

Cheerful & Spacious Shore Life Beauty!

RebeccaRating, 5 stars3 days ago

Extremely comfortable accommodations. Loved all the cozy touches in the apartment. Access was simple. Privately located. Host was very friendly and very responsive.

4.88 out of 5 average rating, 34 reviews

Home in Riva

Waterfront Annapolis Getaway!

NicholeRating, 5 stars4 days ago

Beautiful place with a lovely spot on the south river. Loved the views and how the space allowed the views to really shine. Comfortable, clean, would stay again if I come back to the area. Very peaceful and what I was hoping for. (And not far to town/other things either!)

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!

5 out of 5 average rating, 36 reviews

Waterfront Chesapeake mansion - Panoramic Bay view

ShadRating, 5 stars3 weeks ago

We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

4.95 out of 5 average rating, 19 reviews

Bayou on the Bay

ZaneRating, 5 stars8 months ago

Shelly was a very responsive and friendly host and the home was lovely with an amazing view!

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