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Pet-friendly vacation rentals in Dorchester County

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Dorchester County pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
A serene seating area is presented, featuring two plush pink chairs positioned on a decorative rug. A stylish chandelier adds soft lighting above. A fireplace mantel is adorned with a floral arrangement, and glass-paneled cabinets are visible in the background.
Home in Cambridge
4.86 out of 5 average rating, 64 reviews

High St. Art Gallery Suite

I'M JenaRating, 5 stars3 days ago
Great stay for 1-2 people. Nice kitchen and bathroom, comfortable bedroom. The temperature adjustment happens remotely (you have to text/call someone for that) so it's good to bring an extra layer if you run cold. I had a short stay and was busy visiting my family so I didn't message the host about anything, but everything felt accessible and there were clear instructions regarding checking in and out. I would book again!
Top guest favorite
Home in Deal Island Historic District
4.97 out of 5 average rating, 29 reviews

Rusty Anchor

RachelRating, 5 stars2 weeks ago
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.
Guest favorite
The exterior of a newly renovated home is displayed, featuring a symmetrical design with a central door and large windows. Lush green grass surrounds the house, while several trees provide shade. A dog is seen on the lawn, contributing to a relaxed atmosphere.
Home in Madison
5 out of 5 average rating, 11 reviews

Madison Bay Getaway

MaryRating, 5 stars1 week ago
Great place for a pet friendly quiet family getaway. The back porch overlooking the water provided a peaceful and relaxing place to enjoy the views. Our family enjoyed the updated kitchen and the welcoming living spaces provided a wonderful place to hangout and spend time together. We enjoyed sitting out on the back porch/sunroom with our dog and taking in the views of the water. The large table on the porch made a great place for family game night and the perfect spot to enjoy some local steamed crabs we picked up. The host was very responsive and made us feel welcomed and at home. Thanks for a great stay!
Top guest favorite
A charming white cottage with a steep roof is set amidst lush green trees. A brick walkway leads to the front door, bordered by manicured grass and potted plants. The exterior features large windows that enhance its inviting appearance.
Home in Cambridge
5 out of 5 average rating, 21 reviews

Charming cottage, 1 blk water, historic area

MelissaRating, 5 stars1 day ago
Karyn's cottage was lovely! It was just as it appeared in the photos and is located in a beautiful, peaceful end of town near the water. We really enjoyed all the special touches including fresh flowers, wine & cheese (along with other snacks) and a friendly welcome note. The house is very clean and thoughtfully set up. Karyn has clearly put a lot of attention to making this a pleasant place to stay. She was also easy to get in touch with. I highly recommend staying here!
Guest favorite
A dock extends over calm waters, framed by a vibrant sunset showcasing hues of orange and purple. A picnic table is positioned on the dock, and a flag gently flutters nearby, enhancing the peaceful scene.
Home in Deal Island Historic District
4.94 out of 5 average rating, 32 reviews

House of the Setting Sun/Deal Island Bayfront Home

DawnRating, 5 stars3 weeks ago
Once again, our family had an awesome stay in this beautiful home. Definitely will be back..
Guest favorite
A welcoming living area features a brown leather sofa centered on a wooden coffee table, adorned with flowers. A green front door is visible on the left, leading to an entryway. Adjacent dining space can be seen through an archway, with a chandelier above a dining table.
Home in Cambridge
4.86 out of 5 average rating, 51 reviews

Talbot Corner: Dog-Friendly 3-Bedroom Home

SusanRating, 5 stars2 weeks ago
GREAT location for the Eagleman! Loved that the event was a short walk away. Also great location for exploring downtown Cambridge (check out the Harriet Tubman mural near the museum and the 2022 statue in front of the courthouse) and the Choptank lighthouse. Also lovely neighborhoods to stroll through along the river. We enjoyed our stay!
Guest favorite
A covered porch features two wooden rocking chairs with blue cushions, positioned beside a white railing. Lush green grass and trees can be seen in the background, creating a peaceful outdoor setting.
Home in Cambridge
4.96 out of 5 average rating, 23 reviews

Relaxing Retreat on the Hudson

HowardRating, 5 stars1 week ago
Took the family here (grand parents, 2 babies). We had a great time. Mike's place was clean and modern and well designed. It was well equipped for getting some work done remotely. The family enjoyed catching a bunch of crabs and harvesting some oysters right off the dock in his backyard. Mike was also very responsive to any questions we had. Would def come back at some point in the future.
Guest favorite
A modern kitchen features a central island with a bright countertop and a small plant centerpiece. Stainless steel appliances line the walls, complemented by light-colored cabinetry. Natural light enters through sliding glass doors, while stylish pendant lights hang above the island.
Home in Princess Anne
4.94 out of 5 average rating, 16 reviews

Peaceful Home Away from Home

CharlieRating, 5 stars2 days ago
A lot better than I expected. Very clean, roomy and excellent hospitality. It was the best choice ever with airbnb.

Pet-friendly home rentals with a pool

Top guest favorite
A private in-ground pool is surrounded by a spacious patio, featuring lounge chairs with blue striped cushions. A small cottage is visible in the background, framed by trees and greenery, offering a peaceful outdoor retreat.
Guesthouse in Cambridge
5 out of 5 average rating, 15 reviews

The Place in Cambridge-Summer is in the Air!

PhilRating, 5 stars2 weeks ago
Catherine’s place was perfect location for Ironman eagleman. We were able to walk everywhere we needed to go. The place was clean, quiet, and comfortable. Being able to cool off in the pool was great. They were very friendly and I would stay again.
An aerial view captures a sprawling waterfront retreat surrounded by lush greenery. A private beach area is visible along the water's edge, with a wooden dock extending into the bay. The property features a large house with patios, nestled among trees under a clear sky.
Guesthouse in Cambridge
4.67 out of 5 average rating, 3 reviews

Amazing Waterfront Cottage

ThomasRating, 5 stars9 months ago
I absolutely loved the stay at Cynthia’s riverside cottage. It was off the beaten path, which made it private and peaceful; exactly what I was looking for. It was a bit expensive for just one guest, but given that the Ironman race was happening that weekend, I found the price to be very reasonable. If you have two or more guests, the price is excellent and well worth it for the location. If I ever return to Cambridge, I won’t hesitate to book this stay again!
Guest favorite
Aerial view of a home with a fenced swimming pool, surrounded by lush green grass. The pool features a clear blue water, and several lounge chairs are positioned around its edge. Steps lead from the house to the outdoor area, enhancing accessibility to the pool.
Home in Ridge
4.9 out of 5 average rating, 58 reviews

Waterfront Paradise with a Private Pool

BrittanyRating, 5 stars2 weeks ago
Such an amazing place! Joanne was super responsive and flexible. The views were unmatched! Perfect Mommy and Daddy getaway and we will certainly be back with the kids!
A circular fire pit is set on a concrete pad, surrounded by a grassy area. A wooden fence provides privacy, while a white house with a sloped roof is visible in the background among trees. Additional structures can be seen to the left.
Home in Cambridge
4.78 out of 5 average rating, 9 reviews

Outrigger at Swan Cove Manor

SherylRating, 5 stars19 months ago
Kelly was a great host! She responded quickly to all texts and provided information about things to do in the area- we wven asked her about pizza delivery and she got back to us quickly with a suggestion.
The open living area features a spacious leather sofa and two blue armchairs arranged around a wooden coffee table. A ceiling fan is visible above, and a large flat-screen TV is mounted on the wall. Natural light enters from nearby windows, illuminating the serene blue walls.
Townhouse in Cambridge
5 out of 5 average rating, 4 reviews

Walk to Dtwn: Waterfront Eastern Shore Townhome!

TerryRating, 5 stars1 month ago
Very walkable community and a lot of places to sit and enjoy the water. The neighbors were welcoming and we had no issues with parking. This place is better than the description because of the amenities alone. There was not a single thing we needed while using the kitchen. There's an airfryer, kettle, rice cooker/veggie steamer, blender you name it. There's all the trappings of home so you don't have to pack your entire house when you visit this gem of a location. If travels send me this way again, I'll book here again.
Superhost
A spacious outdoor view showcases a well-maintained cottage alongside a large swimming pool. The area is surrounded by expansive lawns and trees, creating a sense of privacy and tranquility. A pool house and barn are visible, offering additional outdoor recreational spaces.
Cottage in Trappe
4.87 out of 5 average rating, 30 reviews

Private Waterfront Cottage on Bolingbroke Creek

IsaiahRating, 5 stars10 months ago
Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.
Superhost
A serene waterfront scene captures a vibrant sunset, with a silhouetted tree and a pier extending into the water. The sunset's warm colors reflect gently on the surface, creating a tranquil atmosphere amidst the natural landscape.
Home in Woolford

"Endless Summer" on the Chesapeake!

JeannineRating, 5 stars1 month ago
great location and very clean!
A spacious bedroom features a large white bed with decorative pillows at its center. Light wood flooring extends across the room. A ceiling fan is mounted above, and a television sits on a wooden dresser. Natural light fills the space through windows in the background.
Guest suite in Cambridge

Waterfront Getaway for Two

SandraRating, 5 stars26 months ago
It really is a private space. My husband and I had a great time, my husband and I enjoyed this stay. It's a wonderful stay. We would really like to return Kelly. She was very kind and attentive in case we needed anything.

Private, pet-friendly home rentals

Superhost
The image captures a vibrant sunset over the water, featuring colorful clouds and a serene horizon. Tall grasses border the foreground, enhancing the natural beauty of the waterfront location. Soft rays of light emerge from the clouds, creating a peaceful atmosphere.
Home in Westover
4.94 out of 5 average rating, 82 reviews

Beachfront Chesapeake Bay Retreat

MarvinRating, 5 stars3 weeks ago
I loved it, very comfortable, nice beach and organized, I recommend it
Guest favorite
A private pier extends into the calm waters, framed by silhouetted posts. The sun sets on the horizon, casting soft oranges and yellows across the sky. Outdoor seating is visible in the foreground, providing a perfect spot to enjoy the serene view.
Home in Cambridge
4.88 out of 5 average rating, 52 reviews

Waterfront, amazing views, pier, fishing/crabbing

SandyRating, 5 stars9 months ago
The house are clean, bright with a great view. We had a wonderful time and were lucky to have wonderful weather during our stay! We also had a lot of fun playing Mad Gab and other games in the games chest. We were successful in catching some fish and plenty of crabs. It was a great vacation. We enjoyed it very much.
Top guest favorite
A well-maintained green lawn extends toward the water, bordered by tall trees providing shade. The view includes the distant waterfront and a pier, with a clear blue sky above, creating a sense of openness and tranquility.
Home in Cambridge
5 out of 5 average rating, 34 reviews

Serene getaway with great waterfront views!

EugeniaRating, 5 stars9 months ago
We recently had a wonderful stay at Travis's place, and we couldn't have felt more at home. The house is not only beautiful but also comfortable, making it the perfect retreat. It’s one of the best-stocked homes I’ve encountered on Airbnb, which made our stay even more enjoyable. Travis was a wonderful host, always responsive and ready to assist with any questions. I truly hope to return in the future. Thank you, Travis, for hosting us in your lovely home!
Guest favorite
A covered patio features two cozy hammock chairs suspended from the ceiling, creating a relaxed seating area. Sunlight filters through, casting soft shadows on the wooden floor. The view includes a quiet street with neighboring houses and greenery, offering a serene outdoor space.
Home in Trappe
4.88 out of 5 average rating, 98 reviews

Cozy & Spacious, The Calway Inn

ChrisRating, 5 stars5 months ago
Cozy house, very comfortable, easy to find, near enough to major roads to be convenient for exploring, but quiet and private. Jefferson was super easy to work with. A real find.
Guest favorite
Home in Scotland
5 out of 5 average rating, 10 reviews

Water House at Scotland Beach

Mary EmmaRating, 5 stars1 month ago
In decades of renting beach houses, hotels, seaside resorts, Air BnBs, etc., I don’t ever think I’ve enjoyed a home or location as much as Water House. The setting brought us such joy - the oaks, the river birches, the fig trees, the magnolia, the loblollies, of course Tanner Creek. And your design aesthetic is so welcoming and elevating. Everything about the interior and exterior of the home is wonderful. Thank you for putting such obvious thoughtfulness and care into your home and its landscape. And what a great location near that wonderful state park. This was our first time in St. Mary’s County and I learned so much about its pre-colonial, colonial, revolutionary, 1812 and of course civil war history. It was a real revelation and Water House was the perfect HQ for those explorations. We also encountered wonderful people in the park and the local restaurants. It was just a perfect stay. Thank you!
Guest favorite
A two-story gray house is depicted with large arched windows and a welcoming front porch. The structure sits on stilts above the water, while a wooden dock extends towards it, surrounded by quiet water and greenery. The sky displays soft evening light.
Home in Scotland
5 out of 5 average rating, 33 reviews

Bay Front Beach House

JenRating, 5 stars3 weeks ago
We booked this place for a weekend getaway with our little ones. It was absolutely the perfect place for what we were planning! The private beach was PERfECT for young children! the kids loved being able to ride their scooters under the house. We got some fishing in, daughter was a spot master! The hammock was lost in a storm before we arrived, but our superhost made sure we could enjoy a hammock!! upon hearing that it was the top of the list of kids wish list, she took time out of her day and drove all the way and installed a new hammock for us!! Was even so considerate to offer to pick up any needed items. I believe more than the kids, my dog had the time of his life!! They even had doggy bowls ready!! We will definitely be back!! This place is awesome!! Thank you Dana for you gracious hospitality!!
Guest favorite
An aerial view captures a serene waterfront retreat surrounded by dense trees and a winding creek. The house is nestled within the lush greenery, providing a sense of seclusion and harmony with nature.
Home in Ridge
4.93 out of 5 average rating, 54 reviews

Private Waterfront Retreat | Chesapeake Sunrise

CatherineRating, 5 stars4 weeks ago
We had a wonderful stay! The location was absolutely beautiful, and my family especially enjoyed having access to the private dock. We used the stand-up paddle boards, kayaks, and canoes every day after giving them a quick clean. The paddle boat didn’t work quite as expected, but we made it work with some oars and still had a great time on the water. The house itself was clean, comfortable, and well-stocked with everything we needed to prepare our own meals. The host also provided excellent local recommendations, which helped us make the most of our trip. Overall, it was a fantastic getaway, and I would definitely recommend this Airbnb to others!
Top guest favorite
A spacious game room showcases a sleek pool table, inviting friendly competition. A comfortable seating area is available, complemented by decorative elements that highlight the 'Bliss on the Bay' theme. Natural light fills the room through large windows, creating an inviting atmosphere.
Home in Scotland
5 out of 5 average rating, 22 reviews

Scenic Bay Hideaway: Peaceful Vibes & Beach Access

NicholasRating, 5 stars4 weeks ago
Tricia was incredible and her place is beautiful, clean and fun! She has provided lots of additional, thoughtful and couldn't have been nicer. Highly Recommend for anyone who is looking for a peaceful, beach getaway!

Destinations to explore