Vacation rentals in Somerset County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Somerset County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

Hotel room in Crisfield

5 out of 5 average rating, 3 reviews

The Cove - 9 Rooms and Conference center

EamonRating, 5 stars20 months ago

Wide open space for our event with a sink, full sized fridge, and mini ice maker. Lots of tables and two bathrooms there as well. 9 hotel style rooms with Jacuzzis, bathrooms, AC, and more. Complimentary gifts and great recommendations along with prompt and helpful responses. My only suggestion is to better sell how good this property is. As of writing this review, the page says there are only 6 beds but there are nine. The pictures of the event area don't properly convey how large and nice it is. Very happy with everything and I'm already trying to find a reason to book this location again next year.

Top guest favourite

Home in Deal Island Historic District

4.97 out of 5 average rating, 58 reviews

"Promise Point" Bay front home with dock. 3BR 2BA

JeromeRating, 5 stars3 months ago

Me and my family we enjoy the beautiful scenery and Frank beautiful Home. It is truly five stars. It’s a place that everyone needs to go visit. I’m not just saying this just to say it I’m saying because it is so true. We really enjoyed the stay , relaxing atmosphere And the calmness that it brought me and my family. The house is big roomy clean comfortable it’s one of my best Airbnb home that I rented, you won’t be disappointed. This is a place you must see.,appreciate Frank and his family for letting my family enjoy their beautiful Home Thanks

Top guest favourite

Cottage in Westover

4.99 out of 5 average rating, 215 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

BarbaraRating, 5 stars1 month ago

I picked this beautiful home to stay in while I did some nature photography in the area (in February) because I liked the proximity to the public natural areas. Kristina was an excellent host, very responsive to messages, and her home is gorgeous, extremely comfortable, welcoming and nicely stocked with paper goods and linens. I hope to return to explore the area in a different season and would love to stay in her home again! If you’re looking for fine dining and nightlife, this is not the right location for you, but if you want to enjoy peace, quiet, and nature in a very tranquil setting, I highly recommend this home! Thanks, Kristina!

Top guest favourite

Cabin in Westover

5 out of 5 average rating, 44 reviews

Chalet Style Home, private country setting

AprilRating, 5 stars3 weeks ago

I recently stayed at Crooked Elm and was thoroughly impressed. The place was impeccably clean, and the attention to detail was evident in every corner. The host's responsiveness was top-notch! One feature that stood out was the guest binder. It was incredibly detailed, providing clear instructions on everything from using the fireplaces to local attractions and dining recommendations. This made it easy to settle in and feel at home. It had everything we needed for a cozy stay! Overall, my stay at Crooked Elm was delightful, and I highly recommend it to anyone looking for a cozy, well-managed retreat.

Guest favourite

Condo in Crisfield

5 out of 5 average rating, 29 reviews

Breathtaking Waterfront Penthouse with Boat Slip

FranRating, 5 stars3 months ago

Greetings, My family and I decided to go away this year for the Thanksgiving Holiday 2024. We stayed at this Beautiful Condo in Crisfield MD from Wed. Nov. 27th -Saturday Nov. 30, 2024 The price was very affordable which made our decision to stay that much easier. Our check in process was effortless. Our host, Marietta provided the information needed to gain access to the property in a timely manner. Parking pass were readily available for our vehicles and the neighbors we met when entering into the building were very friendly. The decor at this property is fabulous, the entire unit is spacious, squeaky clean, neat and well organized. It was really our home away from home. The views from this 5th Floor unit are breathtaking and even though the weather outside was frosty, which prevented us from lounging on the balcony to take in the scenery. We simply enjoyed the inside warmth from the gas burning fireplace and the view of the marina so soothing and relaxing. Satisfied 🥰

Top guest favourite

Home in Crisfield

4.96 out of 5 average rating, 280 reviews

Cozy Home near Waterfront in Crisfield, MD

CaitlinRating, 5 stars1 month ago

I got this home for my mom to use when she came to visit. It was perfect! Just the right size, super clean, easy to the water (which is her favorite place!) and close to everything she needed! There were waters and snacks already there for her and she loved how quiet and peaceful it was! We will definitely use it again!!

Guest favourite

Cottage in Westover

4.94 out of 5 average rating, 186 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

ClaraRating, 5 stars1 week ago

We really enjoyed the comfort and cleanliness of this home. We had everything we needed for a peaceful getaway, with a well-equipped kitchen to cook in and warmth provided by the wood burning fireplace in the living room and a propane one in the kitchen. Lots of windows provided a view of the bay and each morning we awakened to a different look and feel in the water and sky. The sunsets were truly spectacular. It is a bit removed from restaurants and grocery stores but if peace and beautiful surroundings--and what looks to be active water sports activities during the summer--are what you're looking for, this is the perfect place.

Superhost

Home in Westover

4.94 out of 5 average rating, 31 reviews

Private beach with comfort

AmyRating, 5 stars6 months ago

if you need a place with privacy and respite with beautiful sunsets this is the place to go. we took our dogs and it was great for our dogs in that there was an outdoor deck that was fenced in as well as a yard area for the dogs to go to the bathroom in a little spot on the beach to take small walks. I also took my elderly mom and she appreciated the ramp as well as the low shower in the main floor bedroom. this place accommodates elderly, dogs, kids, people who want to do water activities, or people who just want to get away and rock in a rocking chair. there were a lot of games and activities in the house for probably ages 12 and up. host was absolutely fantastic as well

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Other great vacation rentals in Somerset County

Guest favourite

Cottage in Wingate

4.85 out of 5 average rating, 68 reviews

Blue Crab Cottage: Remote+Nature+Fishing+Views

JustinRating, 5 stars2 months ago

Extreme cold weather came in and froze the water pipes; jody was up front with the issue and refund my money and i was able to get other lodging, but still had a great trip. Id book again with her.

Apartment in Crisfield

5 out of 5 average rating, 3 reviews

Waterfront Condo Getaway

ShannonRating, 5 stars18 months ago

We had a lovely stay! Everything was as advertised and the location and view were beautiful. Everything we needed was readily available and was amply stocked. Overall it was a great experience. Thank you!

Top guest favourite

Home in TYLERTON

4.95 out of 5 average rating, 131 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

SusanRating, 5 stars2 months ago

Our stay exceeded all expectations! Duke is an excellent communicator, the village is welcoming, the home is comfortable, the decor is a reflection of life on Smith Island and we look forward to planning our next visit! Be sure to visit the local Market for delicious crab cakes and famous Smith Island cakes. We highly recommend this beautiful Smith Island Bungalow for a quaint getaway!!

Superhost

Home in Princess Anne

4.9 out of 5 average rating, 10 reviews

countryside home in Princess Anne

CariRating, 5 stars3 weeks ago

The house was very comfortable and warm. The fireplace was the go to place to be. The house is well laid out and nicely styled. Many thanks for allowing us to use your lovely home.

Guest favourite

Home in Marion Station

4.89 out of 5 average rating, 18 reviews

Waterfront Marion Station Retreat w/ Private Dock!

Luis RRating, 5 stars3 weeks ago

Excellent, beautiful and clean house, we recommend to anyone who’s looking for a high end stay. Our host was amazing, friendly and very supportive.

Guest favourite

Vacation home in Toddville

4.92 out of 5 average rating, 13 reviews

Goose Creek Shore House

JohnRating, 5 stars5 months ago

Highly recommend this place for anyone looking to retreat from the hustle and bustle of daily life. Very quiet and removed. Stephen was a great host, very quick to respond and was able to make our stay very enjoyable.