
Holiday houses in Somerset County
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Top-rated holiday rentals in Somerset County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Somerset County holiday rentals
Other great holiday rentals in Somerset County

Apartment in Crisfield
5 out of 5 average rating, 3 reviewsWaterfront Condo Getaway
ShannonRating, 5 stars20 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!
Guest favourite

Home in Smith Island
5 out of 5 average rating, 11 reviewsHH Ranch on Smith Island w/ Golf Cart
JonRating, 5 stars4 months ago
This house is truly a hidden gem on the island. It’s fully stocked and beautifully furnished, catering to all types of travelers—whether you’re an adventurer looking to explore or someone like me who enjoys relaxing at home. Everything you could possibly need is right here, making it perfect for a peaceful getaway or an unforgettable vacation. I absolutely loved my stay and can’t wait to return in the near future!
Top Guest favourite

Apartment in Crisfield
5 out of 5 average rating, 7 reviewsNewly renovated 3 Bedroom Condo
LaurenRating, 5 stars7 months ago
We’ve stayed at several of the units in this same complex, Kelly’s was by far the nicest. Can’t beat the view of sunsets on the patio!
Guest favourite

Home in Quantico
4.98 out of 5 average rating, 102 reviewsOne of a kind waterfront home with private dock
AliciaRating, 5 stars8 months ago
This was our third year at this house. We love it here! We hope to come back next year!
Top Guest favourite

Home in TYLERTON
4.95 out of 5 average rating, 132 reviews3 bedroom/2.5 bath Smith Island bungalow with dock
SusanRating, 5 stars3 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!!

Cabin in Deal Island Historic District
4.8 out of 5 average rating, 5 reviewsRRR remote rustic retreat
TravenRating, 5 stars2 weeks ago
This is a great location and a jewel in the rough.. a classic seaside cottage. If you are looking for a sanitized "fake" shore location this is not it. Deal Island is an old working harbor and the cottage is a lived in and homey eclectic place. The views are amazing, the rooms and layout are fun. There are some details that are worn, but they do not effect the stay. Its a great place to retreat and to connect with the elements and nature! David was very helpful and responsive! Highly recommended for a rural retreat, peace, quiet and nature on the water!
Superhost

Home in Princess Anne
4.9 out of 5 average rating, 10 reviewscountryside home in Princess Anne
CariRating, 5 stars2 months 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, 19 reviewsWaterfront Marion Station Retreat w/ Private Dock!
CheriRating, 5 stars1 week 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.
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- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Northside Park
- Heritage Shores
- Jolly Roger at the Pier
- Bayside Resort Golf Club
- Gerry Boyle Park
- Haven Beach
- Bow Beach
- Ragged Point Beach
- Guard Shore
- Wallops Beach
- Langford Sand
- Saint Jerome Beach
- Plantation Lakes Golf and Country Club
- Trimper Rides of Ocean City
- Lost Treasure Golf
- Assateague State Park
- Lane Beach
- Piney Point Beach
- Parramore Beach
- Snead Beach