Holiday rentals with a fireplace in Talbot County

Apartment in Stevensville

4.98 out of 5 average rating, 278 reviews

Boutique by the Bay

StephanieRating, 5 stars2 weeks ago

What a beautiful space! The neighborhood was quiet and scenic but close and convenient to major attractions. The decor and furniture are beautiful and comfortable. There are lots of nice touches to help make your stay comfortable-we loved the snacks! We were very appreciative of how friendly and responsive the hosts are and would definitely return in the future.

4.93 out of 5 average rating, 225 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!

4.86 out of 5 average rating, 125 reviews

Home in Saint Michaels

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Townhouse in Tilghman Island

5 out of 5 average rating, 44 reviews

Tilghman Island Waterfront Home w/Stunning Sunsets

Tilghman Island, MD Waterfront Townhome - 1 master bedroom suite + 1 other bedroom Immerse yourself in luxury (with a casual vibe) at our newly renovated home with sunrise & sunset views. Discover the Watermen's way of life. Find peace, wildlife, history, great fishing, blue crabs and oysters. The marina offers boat rentals to explore the marshes, bay, and/or rivers. Our home faces West for panoramic sunsets over the water. Cozy up on the sofa to read or watch a show on the large screen TV.

4.88 out of 5 average rating, 43 reviews

Cottage in Easton

Loon Cottage on Leeds Creek

Loon Cottage is a place where you can get away, put your phones down, take long walks in the woods, read on the patio, canoe on the river, cook big meals, and spend time with your favorite people. It’s cozy, comfortable, and just a little bit nostalgic. Decamp from the City to work remotely for a few days. Bring the family out to change the scenery on your weekend routine. Pack friends into the car for some low key shenanigans. Or some combination of all the above. Follow along @loon_cottage

4.95 out of 5 average rating, 98 reviews

Home in Preston

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or kayak, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Superhost

Home in Queenstown

4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

4.99 out of 5 average rating, 121 reviews

Guesthouse in Cambridge

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

5 out of 5 average rating, 102 reviews

Home in Saint Michaels

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

5 out of 5 average rating, 18 reviews

Home in Tilghman Island

Panoramic water views

Tilghman Island Point of View. Our Island is perfectly situated on the Maryland crab and oyster trail. Step back in time to a slower lifestyle and observe the waterman’s way of life. Enjoy our two-bedroom coastal cottage and Island attractions. Enjoy the bird’s eye view of the local waterman in and out of the harbor seeking the days catch. Walk or kayak the shoreline. Take a stroll or ride a bike to Island attractions including all restaurants and shops. Arrive by boat or car.

Guest suite in Tilghman Island

4.97 out of 5 average rating, 146 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

4.99 out of 5 average rating, 171 reviews

Home in Saint Michaels

Grace Cottage, Saint Michaels Walk to everything!

Welcome to Grace Street Cottage with a newly renovated kitchen! Located in the heart of Saint Michaels. Walk to shops, restaurants and experience the best of the Eastern Shore. This cottage has all you will need for a perfect getaway. Sit by the fire pit and grill out or take a few steps to Talbot Street where your dining options are endless! Pack your bags and head to the shore! The experience awaits you!

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Popular amenities for Talbot County Accommodation with Fireplace

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Air conditioning

Holiday House Rentals with a fireplace

5 out of 5 average rating, 8 reviews

Home in Easton

Ferry Bridge House

ColleenRating, 5 stars5 months ago

Beautiful property - everything was just as advertised and more. Spacious bedrooms with comfortable beds. Quiet, private location with gorgeous views. The hosts were exceptional - very gracious, thoughtful and accommodating to any possible need. We were delighted to find the house so beautifully decorated for Christmas. It made for a very special stay. Thank you!

5 out of 5 average rating, 20 reviews

Home in Annapolis

Charming 4BR, 3BA Steps from the water.

StevenRating, 5 stars2 days ago

The house was beautiful. Perfect for our two families that stayed for a long weekend. Kitchen had everything needed and there were stores really close by to get everything we wanted eat and drink. Gwen was proactive in communicating and always very responsive. Loved our weekend here and would recommend to anyone!

4.96 out of 5 average rating, 26 reviews

Home in Cambridge

Spacious Historic Craftsman only 3 blocks to water

KennedyRating, 5 stars1 week ago

This was great for our stay in town for the Ironman 70.3! Walkable to the race venue and a great neighborhood.

Superhost

Home in Cambridge

5 out of 5 average rating, 5 reviews

Drop Anchor on Brannocks Bay!

LaurenRating, 5 stars2 weeks ago

We absolutely loved our stay at Djr’s place! The home is on a beautiful waterfront property. Sitting outside or on the dock was incredibly serene and peaceful - we could have spent all day outside relaxing. The home itself was spacious and well equipped. While it was a bit too windy during our stay to use the kayaks and paddle boards, we appreciated that they were provided. Host Djr was very easy to communicate with and so kind. We will definitely be back to stay here again!

5 out of 5 average rating, 46 reviews

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

PaigeRating, 5 stars2 weeks ago

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

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.

4.86 out of 5 average rating, 50 reviews

Home in Cambridge

Talbot Corner: Dog-Friendly 3-Bedroom Home

JacquelineRating, 5 stars2 weeks ago

The home is beautiful and well kept. l really enjoyed my visit there.

5 out of 5 average rating, 15 reviews

Bayside Escape

StacyRating, 5 stars7 months ago

Our family loved our too-short stay at Jessica’s lovely home. Mornings looking out on the water and lounging on the outdoor deck were so tranquil. The home has a wonderful orientation and light-filled living area. Plenty of space, well laid-out and just about every convenience one needs in this comfortable abode!

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Apartment rentals with a fireplace

4.94 out of 5 average rating, 17 reviews

Apartment in Annapolis

Crow’s Nest Cottage - Down Under: Chesapeake Bay

RickRating, 5 stars3 months ago

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Apartment in Saint Michaels

4.91 out of 5 average rating, 58 reviews

The heart of St Michaels awaits.

LaurenRating, 5 stars1 month ago

AMAZING location! We loved being able to park the car and walk to the shops, brewery, winery, restaurants, farmers market and more! The place was peaceful which helped since we had a baby with us. We would definitely rent again if we were to go back!