House vacation rentals in Somerset County

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Popular amenities for Somerset County house rentals

House rentals with a pool

Home in Marion Station
5 out of 5 average rating, 6 reviews

Kingsbay Mansion Bayhouse

LianeRating, 5 stars8 months ago
We just returned from a peaceful stay on this very beautiful property! This is not a cookie-cutter mansion, which is a good thing. It has style and charm yet remained very functional for our family vacation. We loved crabbing and fishing off the dock and spent lots of time in the beautifully maintained pool. We brought our two dogs to this pet-friendly property, and they had plenty of room to explore. It is relatively secluded and peaceful, but Crisfield is very close with lots of restaurants, groceries, a marina, etc. There is plenty to do nearby and if you need any suggestions, the very friendly and charming hosts are happy to provide you with recommendations. We will definitely be back to this lovely mansion that manages to be both roomy and cosy at the same time. Thank you!!
Home in Marion Station
5 out of 5 average rating, 10 reviews

Kingsbay Waterside Retreat House

DanieleRating, 5 stars21 months ago
We stayed at this terrific property for our annual family vacation. The vote is in, everyone had a great time! Our hosts David and Jerry were very responsive and helpful and check in was easy. David was there to greet us and give us a quick tour and helpful tips on local activities. The pool was fantastic. It was warm and the perfect spot to hang out during the day. The dock was a great place to walk out to in the morning, watch the lovely sunsets at night, do a little fishing and a great way to launch the stand up paddly boards we brought. The house is great, was clean with plenty of room for a group of 10 (7 adults and 3 teenagers). In the evening we could hang out in the game room and play cards or could hang out and watch TV in the TV room. Both ground floor rooms open to the pool. We also appreciated all the little extras like plenty of garbage bags, paper towels, cleaning supplies, water and more. The whole gang highly recommends this property. Thanks we will be back

Weekly house rentals

Top guest favorite
Home in Saxis
5 out of 5 average rating, 10 reviews

Island Jewell Near Chincoteague

MichelleRating, 5 stars6 months ago
My husband and I booked a last minute anniversary trip and Denise's home was absolutely perfect. This little home was everything that you could want and more for peace and relaxation. Denise was helpful and responsive and accomodated a very late night check in with no problems!
Guest favorite
Home in Marion Station
4.89 out of 5 average rating, 18 reviews

Waterfront Marion Station Retreat w/ Private Dock!

Luis RRating, 5 stars2 months 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.
Home in Deal Island Historic District
4.67 out of 5 average rating, 3 reviews

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

HelenRating, 5 stars7 months ago
Wrote a review immediately on another site I guess, because our stay was awesome! Check-in, house, cleanliness, Amani, etc were Exactly as stated. Gorgeous location for a family get together. We will be back!
Home in Hoopersville
4.55 out of 5 average rating, 22 reviews

Historic Hoopersville Getaway on Chesapeake Bay!

JohnRating, 5 stars10 months ago
This is a wonderful old house that can hold quite a few people who want to get together for a reunion. We had fun playing games and kayaking. We had a couple issues and host Mark was responsive and accommodating. The location is perfect if you want to get away from civilization and just relax on the porch to read a book or watch nature. There is not much internet coverage and you will want to shop for groceries on your way in through Cambridge.
Home in Princess Anne
New place to stay

Private Beach & Fishing Pier: Wicomico River House

Superhost
Home in Crisfield
New place to stay

Somers Cove Lighthouse Theme

Private house rentals

Guest favorite
Home in Saxis
5 out of 5 average rating, 26 reviews

Island Voices In The Wine Near Chincoteague & NASA

TeddyRating, 5 stars7 months ago
Denise’s place was very clean and comfortable, had a great relaxing weekend!
Guest favorite
Home in Crisfield
4.79 out of 5 average rating, 131 reviews

BayTime

JessRating, 5 stars2 months ago
Thank you for another great stay!
Superhost
Home in Westover
4.95 out of 5 average rating, 75 reviews

Beachfront Chesapeake Bay Retreat

AngieRating, 5 stars7 months ago
We enjoyed our stay in Maggie & James’s quaint and cozy home. The area was quiet and like something out of a book with all the locals and marina and restaurant. Our teens enjoyed playing board games from their childhood even though there were games there for their age group. We were gifted a beautiful loaf of sourdough bread from our hosts. So very thoughtful! If you plan to stay there be sure to check the weather and high tide schedule due to coastal flooding. You’re between the sound and the marshes and low roads can get covered with water. If you’re arriving at night it can be difficult to see where the road ends and the marshy area begins. We enjoyed our stay and our teens want to return when we can have more time sitting out on the beach by the water which is just a few steps from their home.
Superhost
Home in Saxis
4.86 out of 5 average rating, 138 reviews

ISLAND BREEZE Near Chincoteague Island

JustinRating, 5 stars6 months ago
Great stay! Very cozy, beautiful area, beautiful patio free from bugs, will definitely be returning next year.
Guest favorite
Home in Smith Island
4.84 out of 5 average rating, 79 reviews

Smith Island Spectacular Sunsets!

JuneRating, 5 stars6 months ago
The journey to Tylerton is part of the experience. The house has a special nook and cranny kind of fun, lots of sleeping space, and a good location. Kept really clean and easy to operate.
Top guest favorite
Home in TYLERTON
4.95 out of 5 average rating, 132 reviews

3 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!!
Top guest favorite
Home in Crisfield
4.96 out of 5 average rating, 282 reviews

Cozy Home near Waterfront in Crisfield, MD

CynthiaRating, 5 stars3 days ago
We have stayed at Noah's place a few times and always felt like its home. We contacted Noah a few times and he always responded positively. Noah gave us a history of Crisfield and place to go and see. Noah always kept us informed on everything. He is the best Host you could ask for. We will stay at Noah's again.
Superhost
Home in Princess Anne
4.83 out of 5 average rating, 24 reviews

Ye Ole Pirate House

JodiRating, 5 stars4 days ago
We had a great stay! Was flexible with our very late check in. Directions to house were great. House was very clean. Each kid had their own room which is helpful with teen girls. We would stay there again!

Destinations to explore