Holiday rentals with a fireplace in Talbot County

4.98 out of 5 average rating, 278 reviews

Flat in Stevensville

Boutique by the Bay

StephanieRating, 5 stars1 week 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, 223 reviews

Home in Stevensville

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.

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, 97 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, 120 reviews

Guest house 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, 100 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!

Guest suite in Tilghman Island

4.97 out of 5 average rating, 144 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

5 out of 5 average rating, 9 reviews

Home in Tilghman

Waterfront Bliss: Ultimate Tilghman Retreat

ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This meticulously designed vacation home is tailored for the ultimate relaxation and adventure, offering a seamless blend of comfort, luxury, and outdoor excitement. Picture yourself returning from an exhilarating day on the Bay, gently mooring your boat to the private dock before plunging into the refreshing pool.

4.99 out of 5 average rating, 169 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!

4.99 out of 5 average rating, 110 reviews

Cabin in Saint Michaels

True St. Michaels 6 Acre Waterfront w/heated pool

TREMEZZO STAY - Spencer Creek Cabin Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD. If you do not see availability for your dates or are looking to sleep more than 8 please visit our additional exclusive listings! Punch Point (sleeps 10) Chesapeake Mansion (sleeps 12) Ranch at Royal Oak (sleeps 12)

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Popular amenities for rentals with a fireplace in Talbot County

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Pool

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House rentals with a fireplace

4.99 out of 5 average rating, 91 reviews

Tranquility on Talbot

JessicaRating, 5 stars3 weeks ago

Mary Beth was an amazing host. She made this vacation extremely stress free! The house was gorgeous, and the location is so peaceful! Mary made wonderful suggestions on places to eat and things to do! She was so accommodating and made this so easy! We will definitely be back to tranquility on talbot! ☺️

5 out of 5 average rating, 19 reviews

Home in Annapolis

Charming 4BR, 3BA Steps from the water.

StephanieRating, 5 stars2 weeks ago

We had the best time at this Airbnb. I booked this house MONTHS ahead of my sister's bachelorette, and the host was very responsive to all of my messages from the very beginning. I did ask for an early check-in (whatever that may have been) and they allowed us to check in a full four hours early, for a small fee. The house is on a quiet street in a nice neighborhood, which was perfect for our lowkey weekend. We did drive into downtown Annapolis for a boat day, brunch, and shopping, all which was very easy to do. The house itself is beautiful and clean. There was plenty of space for our entire party (8 girls) and tons of extra towels for everyone. The kitchen was nicely stocked with every cooking tool we needed, including ice and water bottles in the fridge. They even provided the firewood for the amazing backyard, which for some reason I thought we'd have to find for ourselves. All this to say, book this spot, and pack light, you won't regret it!

4.96 out of 5 average rating, 24 reviews

Spacious Historic Craftsman only 3 blocks to water

HeidiRating, 5 stars2 weeks ago

Great location, very responsive and helpful host, and warm feel to the home. We particularly appreciated the openness of the first floor which was nice for our group to gather. Very clean, all the necessities, great decor reflecting the location. We would stay here again and recommend to others.

4.95 out of 5 average rating, 43 reviews

Hambrooks House - Porched Sanctuary near Choptank

NakeyaRating, 5 stars1 month ago

Loved my stay beautiful home with serene surroundings and lots of local historic attractions. Highly recommend James’ place!

Superhost

5 out of 5 average rating, 5 reviews

Drop Anchor on Brannocks Bay!

LaurenRating, 5 stars1 week 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!

4.88 out of 5 average rating, 98 reviews

Home in Trappe

Cozy & Spacious, The Calway Inn

ChrisRating, 5 stars5 months ago

Cozy house, very comfortable, easy to find, near enough to major roads to be convenient for exploring, but quiet and private. Jefferson was super easy to work with. A real find.

4.86 out of 5 average rating, 49 reviews

Talbot Corner: Dog-Friendly 3-Bedroom Home

AlmaRating, 5 stars4 weeks ago

Elizabeth is an amazing host. Very responsive and helpful. We were participating in a race that was in a park .5 miles from the house so the location was good.

5 out of 5 average rating, 57 reviews

Home in Stevensville

Bayview Bungalow - Water view, EV charging station

JackRating, 5 stars3 weeks ago

There were many more amenities than what was listed. It was much better than most 5 star hotels! The area was really nice and peaceful, all the neighbors just wave hello to each other, large property with BBQ, hammock, shed, table and chairs to just relax outdoors, a tub for an intimate time with a narrow cross table to set down your champagne, etc etc. The kitchen / dining room / family room was a large open area with so many utensils and items of convenience. It is pet friendly and there were items for the pets as well, a first aid kit, etc. It is a beautiful house on one level, very comfortable, extremely quiet and peaceful. Vicky was in communication throughout and gave clear and concise instructions, which made things very easy for us. Upon checking in, there is a booklet with all the guidance and instructions, information on sites to see and things to do, local restaurants, etc. She has really though of many things to make one's stay as comfortable and as easy as possible

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Apartment rentals with a fireplace

4.94 out of 5 average rating, 17 reviews

Flat 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.

4.91 out of 5 average rating, 58 reviews

Flat in Saint Michaels

The heart of St Michaels awaits.

LaurenRating, 5 stars4 weeks 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!