There are a lot of breathtaking bays in the U.S., but if you do not have time to visit them all, you need to pick just several. One bay that you should not skip visiting is Chesapeake Bay. As the largest estuary in the country, Chesapeake Bay boasts crystal blue water, hundreds of fish species and exquisite seafood produce, with the most popular ones are rockfish and oysters. You are also recommended to visit the nearby attractions, such as Colonial National Historical Park, to gain insights into the most important battles in the country. Also, Cape Henry Lighthouse presents a stunning sea view and a lighthouse originated in 1792. Chesapeake Bay also offers plenty of places to stay, from charming cottages to nearby family resorts. For accommodations, read on to find the best pet-friendly vacation rentals near Chesapeake Bay, USA.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and pet-friendly rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 22, 2025.
1. Breathtaking waterfront rental home (from USD 471)
Indulge in the awe-inspiring beauty of the Chester River from this beachfront rental home. The house features a dining area that’s perfect for social gatherings and happy hours, a fully equipped kitchen with new countertops, and a coffee bar. Outdoors, guests can enjoy a sizable deck overlooking the sea, a picnic table nestled beneath a holly tree, and kayaks and paddleboards that are available for use. Pet lovers will also be delighted to know that fur pals are allowed with the host’s approval and for an additional fee of 50 USD.
Located close to Chestertown and Rock Hall, the property offers plenty of nearby activities to keep guests entertained.
2. Contemporary house on Patuxent River (from USD 305)
Situated right on Patuxent River, this vacation home rental near Chesapeake Bay cordially welcomes six people who can sleep comfortably in the six bedrooms available. You can prepare family meals in the fully equipped kitchen. While sipping a cup of coffee, you may be greeted by deer, foxes and ducks, among others, if you are lucky. If you want to bring your pets, only small dogs that weigh less than 25 lbs (11 kg) are allowed and an additional pet fee applies.
Top guest reviews
Host:
the host was very responsive before our staythe owner went out of his way to ensure our stay would be safe from covidpete has a beautiful property and is an excellent thoughtful hostpete is very responsive and you can tell he takes great care of the house and the propertyLocation:
the location is fantasticsoloman's island is a short car ride away for fun food and a good walk along the riverwe had an awesome vacation time at this locationpete's amazing a frame is the place to go for a relaxing time near the waterlocation near calvert cliffs and solomon's island is perfectCleanliness:
the house was very clean and was well stockedRead more reviewsAmenities & Room:
the house was lovely and the furnishings were very comfortable
3. Modern beach house with large windows throughout (from USD 754)
Indulge in a pleasant stay with your loved ones, including your pets at an additional cost, at this modern beach house that offers private balconies for relaxation. Wake up to the gorgeous sunrise and go straight to the kitchen to make a cup of coffee and prepare breakfast. Feel free to use the kayaks for adventure on the water. You can also use the adult cruisers to explore the surrounding neighborhood at extra charge. Large windows have been installed throughout the house to bring in plenty of natural light that you need.
Top guest reviews
Host:
property manager is very responsive to your needs everyone is so friendlythe staff is very helpful thanks ann for supporting my fire building skillsour property manager was super accommodating and responsive to any question we hadLocation:
the property is a great house with an even greater locationbest place to get away from it all and relaxwe will definitely come back to this amazing place and look forward to our next stayRead more reviewsAmenities & Room:
the views are stunning from each roomviews from every room; well-stocked home with a terrific kitchenplenty of bathrooms great communal spaces but also areas for privacythe house was pretty much perfect: extremely large tastefully decorated comfortable and very well-stocked with all amenities
4. Classic cottage with free kayaks and bikes (from USD 225)
Welcome to this cottage rental near Chesapeake Bay and have an enjoyable stay throughout. The cottage offers one bedroom and one bathroom, making it ideal for solo adventurers or couples. Those traveling with pets will be charged with a pet fee and up to two pets of any size are allowed. During the day, you can either kayak or swim on the beach. After, you can ride a bike to get to know the neighborhood.
Top guest reviews
Host:
everyone we saw was very friendlyi definitely recommend bug spray it was very helpful to keep the mosquitos at bayLocation:
very nice walk to the beachgreat place to get away from it allnice short walk to a little beachwhat a great place where we continue to returnCleanliness:
has everything you need and very cleanthe home was clean cozy and quiet and just a short walk from the waterRead more reviewsAmenities & Room:
the house was nicely furnished with a nicely equipped kitchenwe love the space in the bathroom and the bedroom
5. Comfortable house with a screened porch (from USD 304)
You are cordially invited to have a relaxed stay with the best people in your life at this comfortable house that is situated directly on the water. Two bedrooms and one bathroom are available along with a fully equipped kitchen and a living room. The screened porch is the perfect place to relax over a drink and observe diverse wildlife. An additional pet fee applies for the entire visit.
Top guest reviews
Host:
the property manager & owner made sure our stay was everything we expectedmanagers were very responsive and came to say thanks and goodbyeLocation:
great location and tons of fun we will be backthe location was wonderful can’t wait to return in warmer weatherwhat a charming placevery quiet neighborhood and safe for riding the bikes down to the state parkRead more reviewsAmenities & Room:
great place to stay useable kitchen great patio and deck spaces
6. Relaxed house with a cable television (from USD 316)
Situated not far from grocery stores and restaurants, this house promises a relaxed and serene stay right on the shores of the Potomac River. The property offers a fully equipped fishing pier in which you can indulge in a great fishing experience or sunbathe with your furry friends. For entertainment, the house comes with cable television and high-speed internet. An additional pet fee applies if you want to bring your pets.
Top guest reviews
Host:
the contact person was also helpful and contacted me prior to arrivallori was very responsive and a great hostlori was so kind and readily available for any questionsLocation:
the house and location are perfecthaving the beach so close was greateverything you could possibly need is provided and is super convenient - close to so many activitiesCleanliness:
very clean comfortable and well appointed propertythe house was super clean beds were very comfortable and ample fishing gear was availablewe had a wonderful time in lottsburg the house was very clean and had everything we neededit was clean and had cable and internetRead more reviewsAmenities & Room:
we enjoyed the large family room with the wonderful view of the waterwe enjoyed relaxing in the river room and watching the many moods of the river
7. Cozy cabin on York River (from USD 213)
Come to relax at this cabin rental near Chesapeake Bay that guarantees a cozy stay for small families of four. You can watch the spectacular sunset on York River with a glass of wine in your hand for a memorable evening every day. Catch up with the rest of the world when you want to by being connected to a wireless internet connection. Delectable meals can be prepared first in the kitchen and later are brought into the deck for al fresco dining. Before coming to the cabin, let the owner know how many pets you plan to bring and their sizes.
Top guest reviews
Host:
larry and sheila are friendly and accommodating and i felt like a welcome guest in their homeLocation:
the location is perfect and sunsets beautifulgreat little cabin in a great location with everything that you needsuperb location on the york river with excellent screened in outdoor patioCleanliness:
very clean and easy to get tothe cabin is was welcoming very clean and well stocked with linens and towelsvery comfortable cozy and cleanRead more reviewsAmenities & Room:
wifi and tv great for our teenagerseverything was as advertised the cabin was cozy the view was great the sunsets were beautifulalso hot water never really kicked in when showering but the water was warmvery gracious hosts perfect location gorgeous views and comfortable beds
8. Tranquil house with a fireplace (from USD 301)
Say yes to a tranquil stay for as long as you want with days spent at this house that is located by the creek. Equipped with three bedrooms and three bathrooms, the house is ideal for nine people. Catch some fish on the river and later indulge in barbecuing. Stay warm by the fireplace during colder nights and make your evening memorable by the fire pit to roast marshmallows. Let the owner know if you are bringing a dog and it must be less than 50 lbs (22 kg).
Top guest reviews
Host:
owners are exceptionally nicephil was an excellent host who went out of his way to accommodate us and the boysthe property owner is awesome and super easy to get along withLocation:
beautiful location with amazing sunsetsrural setting yet close to attractions and necessitiesvery quiet wonderful placeit's very quiet and prettyRead more reviewsCleanliness:
great clean house with nice outdoor spacesthe house is very clean comfortable and well equippedthis property is absolutely beautiful this home is incredibly clean and well kept
9. Charming house with a large furnished deck
An unforgettable stay awaits if you choose to book this charming house that can be occupied by nine people as it comes with four bedrooms and four bathrooms. Grab your favorite novel and read it on the large deck. Here, you can also absorb the peaceful atmosphere of the surrounding. In the evening, cozy up by the fireplace and pour yourself a glass of wine. The house welcomes pets with an additional pet charge. Upon booking, you need to mention that you wish to bring a pet.
Heathsville, Virginia, United States
14.17 km (8.9 mi) from Point Lookout State Park
Top guest reviews
Read more reviewsHost:
had a few questions about the property the owners were very responsive and eager to assisthouse was as advertised mora was a great host and answered all questions promptly
10. Spacious house with a hot tub
Unwind and recharge at this house that is spacious enough to accommodate up to eight guests. Have a good night’s sleep in the four bedrooms available. There are plenty of amenities that you can enjoy for fun moments, such as a swimming pool for children, a ping pong table and darts. After doing all those activities, find yourself having a refreshing soak in the hot tub. But, you need to shower first before relaxing in the hot tub. As for pets, dogs must be under 50 lbs (22 kg) and cats must have their nails trimmed before arrival. Be sure to clean up after your pets at all times.
Reedville, Virginia, United States
21.82 km (13.6 mi) from Point Lookout State Park
Top guest reviews
Cleanliness:
clean and comfortable houseRead more reviewsAmenities & Room:
this was a great house the kitchen was very well stocked bed linens were comfy plenty of towels
Be prepared to be blown away by the beauty of Chesapeake Bay
Now that you know more about Chesapeake Bay, you just want to be there as soon as possible, don’t you? What are you waiting for then? Start planning your trip and book a pet-friendly cabin close to Chesapeake Bay right away.
If you would like to explore more accommodation options, you can also check out these Airbnb vacation rentals.
Frequently asked questions about the best pet-friendly vacation rentals near Chesapeake Bay, USA
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