
Pet-friendly vacation rentals in Somerset County
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Top-rated pet-friendly home rentals in Somerset County
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Pet-friendly house rentals

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Our host, Leticia, promptly answered my questions with excellent detail. She was very kind and flexible. The house was charming, very comfortable and spacious for our family of five adults. The remodel was done very well and equipped with everything needed. The two screened in porches were a nice addition. The property backs up to the Chesapeake Bay-the view, and sunsets are outstanding! The listing photos don’t do it justice! The blue crabs were meaty and succulent.This was our second time on Deal Island and we plan to return to this house again! Our family needed this R&R weekend! Thank you Leticia and Charlie!

157-Acre Waterfront Retreat
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.

One of a kind waterfront home with private dock
This was one of my favorite stays so far! The location was quiet and peaceful with beautiful views all around. The dock in the backyard was nice, my dogs loved the fenced in yard and big yard to the side of the house. The house was clean and the bed was super comfortable. I can’t wait to come back! 😊

Home in historic village of Whitehaven, Maryland.
We had such a great experience staying at White Haven, definitely a beautiful and peaceful retreat!

Charming Crisfield Cottage
Ideal location, great area for outdoorsmen. The cottage is incredibly convenient. Grocery store is very close. Nestled between Salisbury and Pocomoke. Crystal is very accommodating.

The Salt Marsh Shanty
This is a special house and my kids and I felt immediately at home. The marsh is otherworldly beautiful and we appreciated the access to the kayaks, crabbing equipment, and grill. The sun rise and sunset alone were worth every penny. We gave already decided we want to make it a place we go to throughout the year!

Peaceful Waterfront Home w/ Kayaks & Fire Pit
Wonderful, clean and charming historic house and great location! Was the perfect place to stay with a group of friends for a long weekend. House is even better than it looks in the pictures and the view is fantastic. The host was super accommodating and we loved having access to their grill, bikes, kayaks, and paddle boards.

Deal Island Lodge
I loved this beautiful place. It's clean , and on a beautiful piece of property. The host has great communication
Pet-friendly home rentals with a pool

Kingsbay Mansion Bayhouse
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!!

Kingsbay Waterside Retreat House
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

Farmhouse located on a horse farm
Our stay was nothing short of amazing. The house was better than described, and the hosts were so accommodating. Everyone we encountered on the farm was extremely friendly. Everything was perfect from the comfy beds, refreshing pool and the beautiful landscape.

Creek House - Luxury Waterfront on Holden's Creek
We all really enjoyed our stay. We had a great time making and eating our meals, sitting on the various porches watching the creek and all the birds, exploring the grounds, and using the canoe. The peace of the place was wonderful. We especially enjoyed watching the two ospreys nesting across the creek. Allysin stopped by to check on us and was very friendly and welcoming. She was very appreciative of the feedback we provided about a relatively minor issue with the water pressure on the main floor. If we visit the area again, we will definitely consider staying again.

Kingsbay Dockside Waterfront House
The home was beautiful and very clean. The pool was so wonderful to have. It’s definitely out of the way, but the privacy is wonderful.

The Porter's Barn - waterfront w/ dock & fire pit

Beautiful, Waterfront, Luxury
Private, pet-friendly home rentals

BayTime
Thank you for another great stay!

Beachfront Chesapeake Bay Retreat
Fantastic airbnb experience! The house is cozy and comfortable, fits a lot of people, and has so many amenities. You can have a peaceful time without going stir crazy and I didn't have any concerns about anything while there because of the great hosts! Will be back the next time I find myself in the area!

Rusty Anchor
Rustic and charming, the Rusty Anchor was exactly what we hoped for. The screened porch was a favorite hang out spot. The kitchen sink was absolutely adorable. And the host had tons of family friendly amenities available like a baby bath, beach toys, coloring books, and board games. It looks just like the pictures. Her recommendations for the Washington Inn (now Sugar Water), the local beach, and the produce stand were all fantastic. We didn’t want to leave. If you are looking for a low-key, relaxing get-away, this is the perfect place.

Catch of the Bay
Felt like I was home even being away, love the town of Crisfield and this place made us feel safe and secure as well as very Comfortable. We will be back for another short stay again before summer ends.

Private guest suite near Deal Island Maryland
We have stayed with Tim a number of times. We enjoy staying at his Airbnb and going fishing several times a year. I am sure that we will be back.

Water View Cottage
A beautiful water view cottage in a quiet and peaceful setting was precisely what we wanted — and got — during our stay at this home. We couldn’t be happier. Everything was perfect. View of the sunset (which, along with the water) could be seen from inside of the home. This is truly a special little spot that we hope to be visiting again sometime. I highly recommend this rental.

House of the Setting Sun/Deal Island Bayfront Home
Once again, our family had an awesome stay in this beautiful home. Definitely will be back..

Smith Island Yummy Artist Retreat
10/10 if u could give more i would. From the minute we booked to after getting back home Jemma was above and beyond helpful, responsive and really went out of her way to ensure a more than perfect stay for my family. She opened her other 2 homes to us to let us check them out, introduced us to with other locals who were just as friendly and welcoming as jemma: they let my girls check out their goats and roosters and ducks. Jemma was always available and was kind enough to share her 2 island pups with my girls, allowing them to come hang out and visit through out the day. Jemma was there to pick us up from the boat and get us back on. She even went out of her way to make me a bowl of sautéed veggies from her garden when I told her I was craving a salad and couldn’t get one on the island (wasn’t complaining just making mention of it) Her home was beautifully decorated, so much love and detain went into every inch of the house Loved the bathtub and shower the layout the location
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- Chesapeake Bay
- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Northside Park
- Jolly Roger at the Pier
- Assateague Beach
- Haven Beach
- Snead Beach
- Heritage Shores
- Ragged Point Beach
- Plantation Lakes Golf and Country Club
- Gerry Boyle Park
- Wallops Beach
- Trimper Rides of Ocean City
- Oxford Beach
- Assateague State Park
- Piney Point Beach
- Lane Beach
- Parramore Beach
- Gargathy Beach
- Guard Shore