Holiday rentals with a fire pit in Somerset County

4.92 out of 5 average rating, 12 reviews

Home in Smith Island

HH Ranch on Smith Island w/ Golf Cart

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

4.93 out of 5 average rating, 14 reviews

Home in Princess Anne

countryside home in Princess Anne

Escape to tranquility at our private home in the serene countryside. Our spacious and comfortable three-bedroom, two-bathroom home provides ample space for families, couples, and groups of friends to relax and enjoy the outdoors. Relax in the cozy living area, cook a meal in the fully equipped kitchen, or enjoy an evening around the campfire. With comfortable bedrooms and a peaceful location, it's the ideal getaway for a relaxing break. Book now and experience the beauty of rural living!

4.96 out of 5 average rating, 52 reviews

Home in Crisfield

Catch of the Bay

Welcome to the completely remodeled catch of the bay cottage! You will enjoy calling this beachy yet rustic location with a farmhouse theme your home during your stay. The home offers three bedrooms and one bathroom - one king bed, one queen bed, and a set of bunkbeds. There’s also a pull out couch if that more so meet your needs. The home offers a remodeled and fully stocked kitchen, laundry area/mudroom on the inside, as well as a spacious backyard, fire pit in front and rear porches.

5 out of 5 average rating, 15 reviews

Guesthouse in Crisfield

Casa Acuarela

Located on the Eastern Shore of the Chesapeake Bay, Casa Acuarela is more than just a place to spend the night. It is a retreat to spend your day relaxing and enjoying the atmosphere. You can: Meditate in our peaceful zen-like garden in the morning Lounge in the screened tea house for an afternoon time out Light the fire pit at night or sit back and enjoy the lighting Or simply relax in the inviting studio spending quality time reading, watching TV, playing board games and resting.

5 out of 5 average rating, 85 reviews

Farm stay in Westover

Big Cozy Loft Overlooking the Farm and River

The Loft is located above the apiary workshop. It is an expansive king room with bath. Walk-in shower has a rainforest head. Views of the donkey pasture out your window! From one side you have a view of the farm & river, the other apiary, gardens & river. The loft is the perfect place to cozy up. Each morning you will have a farm fresh breakfast. The loft has a small refrigerator, tea, coffee with all your necessities. No WiFi/TV or smoking on property. No children in Loft.

5 out of 5 average rating, 17 reviews

Home in Fishing Creek

Hoopers Island Victorian with 360 Water Views

Chesapeake Bay sunsets & Honga River sunrises. Watermen heading out at dawn for a day's work. Ospreys, herons & egrets hunting for their dinner. A short walk to get crabs harvested just that morning. Everything that makes the Eastern Shore unique—the Bay, windswept marshes, seafood, its deeply-rooted history—in a magical place where time slows down so you can catch up. The ideal spot for nature lovers & those seeking peace, quiet & time to bond with the people they love.

Cottage in Marion Station

4.71 out of 5 average rating, 38 reviews

Year Round Playground - Rare Rustic-Modern Getaway

Enjoy best of Eastern Shore living in this unique property that provides privacy & exciting amenities for everyone: POOL, 7 PERSON HOT TUB, OUTDOOR KITCHEN, REC ROOM, FISHING, w/GOLFING & BEACHES nearby! Newly renovated 3BR/2.5BA offers guests an opportunity to have in-the-woods feelings w/o sacrificing comfort. Escape the city rushes on a rare waterfront property w/private dock on East Creek leading out to the bay! Don’t miss out on Insta-worthy photo ops! BOOK NOW!!!

4.88 out of 5 average rating, 65 reviews

Guest suite in Westover

The Hideaway Suite

Welcome to our humble farmhouse guest suite, your own little slice of tranquility nestled amongst the fields and forests. Tucked away from the hustle and bustle, our home is your perfect getaway, providing peace and quiet while still being conveniently close to Route 13. Once you step inside to the comfort of your suite on the second floor, you're in for a treat with beautiful views and idyllic sunsets. We look forward to hosting you in our lovely farmhouse.

4.97 out of 5 average rating, 29 reviews

Home in Saxis

Marsh View Saxis

We love this home and we hope you will as well, offering a perfect blend of comfort and style with 3 bedrooms and 2 bathrooms, breathtaking views of the wetlands, where sightings of graceful blue herons await you. Step into the spacious living area, where natural light floods the beautiful and bright open kitchen. The large yard surrounding the house provides a serene setting, great for relaxation and outdoor activities including a fantastic firepit.

4.75 out of 5 average rating, 211 reviews

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Home in Deal Island Historic District

4.97 out of 5 average rating, 29 reviews

Rusty Anchor

Escape to the Rusty Anchor, a beautifully restored 1900s farmhouse on Deal Island, MD! With 3 cozy bedrooms, it's perfect for families or friends. Just around the corner, enjoy a cozy beach, crabbing, and easy access to fishing (Redfish, Striped Bass, Flounder) and waterfowl hunting. Only a 5-minute bike ride to beaches and boat ramps. Book now and receive a link to our store to reserve add-ons or schedule special experiences for your stay!

Guesthouse in Deal Island Historic District

5 out of 5 average rating, 34 reviews

Blue Crab Bungalow

Our charming bungalow allows you to relax,refresh and truly unwind while taking in views of the bay. Enjoy amazing sunsets, lots of stars, and the water view from the 2nd story deck, private pier, or around the fire pit. Try crabbing or fishing from the pier. No license needed! A small local beach for swimming and public boat ramp are less than 5 minutes away. We are about an hour to Ocean City, Chincoteague, and Assateague.

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Holiday House Rentals with a fire pit

Home in Deal Island Historic District

4.75 out of 5 average rating, 4 reviews

Reel Relaxation-Waterfront

DeniaRating, 5 stars5 days ago

Holly was an absolutely amazing host—responsive, thoughtful, and kind. We absolutely loved her place and will definitely be returning! I appreciate attention to detail, and it’s clear that Holly truly cares about every guest who stays here. My family and I thoroughly enjoyed our time, and the sunrises each morning were simply breathtaking. We can’t wait to come back!

5 out of 5 average rating, 5 reviews

Home in Pocomoke City

Vacation home near the beaches

NelsonRating, 5 stars10 months ago

Amazing Getaway!! Plenty of indoor and outdoor space, comfortable beds and all around just a wonderful stay. Highly recommend anyone looking for a place to stay with plenty of room and don’t mind a small commute to Chincoteague.

Home in Toddville

5 out of 5 average rating, 3 reviews

157-Acre Waterfront Retreat

JohnRating, 5 stars1 month ago

This place is truly Amazing! This property offers a very unique experience with historical lineage dating back to 1958. We loved how each bedroom is themed with different types of Ducks. I have never stayed in a house with so many features, from fishing, crabbing, kayaking, all the unique antiques and just relaxing. The kids loved all the board games. It was great that we could bring our dog. She loved swimming in the bay. We cooked outside and had dinner on the porch and watched one of the most amazing sunsets over the water that I have ever seen. We had our morning coffee on the balcony off the Pintail room and there was a pair of Eagles perched on the tree. We had a great 5 day stay, we hated to leave! Cindy the housekeeper met us at the house when we arrived, she showed us around to all the bedrooms and the cupola, which is a room on the third floor that has 360 degrees views of the Chesapeake Bay. It’s a great place for groups to gather and create lifelong memories.

4.94 out of 5 average rating, 48 reviews

Home in Quantico

Home in historic village of Whitehaven, Maryland.

SavannahRating, 5 stars3 weeks ago

We had such a great experience staying at White Haven, definitely a beautiful and peaceful retreat!

Home in Saxis

4.78 out of 5 average rating, 40 reviews

Beautiful Bayfront with Sanctuary Private Beach

CaseyRating, 5 stars9 months ago

This home was the ideal setting for our bachelorette getaway. We thoroughly enjoyed the serene waterfront, and having access to the kayaks added a unique touch to our stay. The living room, with its expansive and open layout, was perfect for gathering and enjoying board games together. Thank you for the warm hospitality and for sharing your beautiful home with us!

Home in Nanticoke

4.57 out of 5 average rating, 7 reviews

Historic Country Manor

KristenRating, 5 stars10 months ago

We visit Bivalve/Nanticoke yearly to visit family. This is the first year we had the pleasure of staying at Bryce's airbnb. I highly recommend! She is very communicative, flexible, and support helpful! The home has historic charm with all the updated necessities. Needs are comfy, surroundings beautiful, would absolutely stay here again!

4.9 out of 5 average rating, 20 reviews

Home in Marion Station

Waterfront Marion Station Retreat w/ Private Dock!

CheriRating, 5 stars1 month ago

Our stay was an absolute dream! From the moment we arrived, we were captivated by the stunning views and the soothing sound of the birds and the waves. The house was spotlessly clean and beautifully decorated, providing a perfect blend of comfort and luxury. The kitchen was fully equipped, making it easy to prepare meals while enjoying the breathtaking scenery. We loved the spacious living area, which was perfect for relaxing after a day of exploring. The location was ideal—peaceful and serene, yet conveniently close to nearby attractions and dining options. The outdoor space was a highlight, with a lovely deck where we spent evenings watching the sunset. Overall, it truly exceeded our expectations. We can't wait to return and would highly recommend it to anyone looking for a tranquil and spacious beach getaway.