Last Updated August 31, 2021 8/31/2021

19 Best Chesapeake Bay Vacation Rentals

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The Chesapeake Bay is lined with cute small towns that offer fun things to do and easy access to water recreation. The Bay is about 200 miles long and largely bordered by Maryland and Virginia. There are lots of different places to set up your home base while on a Chesapeake Bay vacation, including rental properties with private pools, that are pet-friendly, and that offer lots of amenities to make your stay cozy and comfortable.

Here are some of the top Chesapeake Bay vacation rentals to choose from.

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Cottage on Solitude Creek, Hot Tub & Fire Pit – Easton, Maryland
Credit: Airbnb.com
Plenty of privacy and amenities to enjoy

Cottage on Solitude Creek, Hot Tub & Fire Pit – Easton, Maryland

With two bedrooms and two baths, this cottage comes with a pool, hot tub, fire pit, and great location near St. Michaels and Easton. The home allows small dogs with a $100 fee. The host lives on site but will give you plenty of privacy. You’ll enjoy the views from the water dock and can bring your boat or kayak along. There are yard games here, as well as a picnic table, and a gas grill for outdoor recreation. The pool is not heated but usually opens in May. Four people can be comfortable staying here in the queen-size beds.

Private Waterfront Retreat – Stevensville, Maryland
Credit: Vrbo.com
True vacation starts right here

Private Waterfront Retreat – Stevensville, Maryland

Available to rent on Vrbo, this waterfront retreat works well for large groups of up to 12 people. It’s a two-story home with a shared pool and hot tub access. The home offers three bedrooms, six beds, and 2.5 baths. You can bring your boat along and tie it up to the dock to go fishing or set out on a sunset cruise. It’s an easy boat ride to get to historic towns and local restaurants. Bridal parties love spending time here. You’ll be in a great location to experience everything that the Eastern Shore has to offer. From here, it’s easy to get to Route 50 and just 15 minutes from Annapolis.

Waterfront Cottage with Pool, Pier & Kayaks – Bohannon, Virginia
Credit: Airbnb.com
An awesome pool for your cottage stay

Waterfront Cottage with Pool, Pier & Kayaks – Bohannon, Virginia

Designed with your comfort and relaxation in mind, this waterfront cottage has a private pool, kayaks, bikes, mini-golf, and is pet-friendly and kid-friendly. Known as the Fish House, it accommodates a family of four and is decorated with eclectic art inside. It’s a two-level cottage that has a gourmet kitchen, TV, grill, and patio swings. The host has another Airbnb rental property onsite too that’s called the Crab Shack. Other great things about this rental are the pier with Adirondack chairs, hammocks, Wi-Fi, and central air conditioning. When you stay here, you’ll be an hour from Colonial Williamsburg and Busch Gardens.

The Barn at Pond Point, Riverfront Home – Cobbs Creek, Virginia
Credit: Airbnb.com
A nice pool for your Chesapeake adventure

The Barn at Pond Point, Riverfront Home – Cobbs Creek, Virginia

A unique way to stay in the Chesapeake Bay region is to rent this barn on Airbnb. It sleeps up to nine people and has three bedrooms and two baths. With this rental, you’ll be on 27 acres of wooded, waterfront property along with the host’s main house. The Piankatank River here is a saltwater arm of the Chesapeake Bay. Guests will enjoy the sand beach, large pool, and well-equipped kitchen here. You can explore all 27 acres of the property during your stay. The pool is only open in the summer. This is a pet-friendly rental except for pit bulls.

Adorable Waterfront Apartment Weekend Getaway – Lexington Park, Maryland
Credit: Airbnb.com
Soak up the sun and views

Adorable Waterfront Apartment Weekend Getaway – Lexington Park, Maryland

You and another person can rent this one-bedroom waterfront apartment on the banks of St. Mary’s River. It offers river views, TV, central heat and air conditioning, a private entrance, and parking for two cars. There’s also a kitchen inside, as well as a work desk, shaded dock deck, gas grill, and complimentary coffee and tea. It’s ideal for two people and has a queen-size bed in the bedroom. From this rental property, you can reach grocery and chain stores within about 15-20 minutes, so consider stocking up on supplies on your way here.

Waterfront Boutique Cottage Getaway Eastern Shore – Onancock, Virginia
Credit: airbnb.com
Waterfront Boutique Cottage Getaway Eastern Shore

Waterfront Boutique Cottage Getaway Eastern Shore – Onancock, Virginia

Here’s a highly rated Airbnb cottage for up to four guests that is a studio space with two beds and one bath. It’s located on Onancock Creek and offers lovely water views through the large windows. This is a private and peaceful escape in the country that is just 10 minutes from downtown Onancock. You’ll love the deck in the back when you’re looking for a getaway on the Eastern Shore. The home is equipped with a smart TV, full kitchen, dock, Wi-Fi, and both an indoor and outdoor shower. There are no laundry facilities here. Bring your own kayaks or paddleboards, or rent them nearby.

The Moore Cottage – White Stone, Virginia
Credit: Airbnb.com
Your own cottage with a cute porch and yard

The Moore Cottage – White Stone, Virginia

Perfect for couples, this rustic-chic fisherman’s cottage has one bedroom and one bath with a location just a mile from Windmill Point Marina. It is five miles from the town of White Stone and overlooks Little Bay and the mouth of Antipoison Creek. The host provides guests with kayaks and a paddleboard to use, as well as life jackets. You can also use the propane grill on the deck to cook out. Other perks are the kitchen, Wi-Fi, and TV with standard cable.

Waterfront Getaway – Stevensville, Maryland
Credit: airbnb.com
Waterfront Getaway

Waterfront Getaway – Stevensville, Maryland

Couples love this guesthouse that’s a private studio apartment on the water and that offers awesome views of the Chesapeake Bay. You can swim in the private pool, fish off the pier, and sit around the fire in the evening. Local beaches are nearby to enjoy. This apartment is above a detached garage that is connected to the main house by an open breezeway. You may see the host family out and using the pool, but you’ll have your own patio and private entrance here. The rental property allows pets under 30 pounds.

Vintage Cabin in the of Middletown – Middletown, Maryland
Credit: Vrbo.com
Such vintage-cool decor and design

Vintage Cabin in the of Middletown – Middletown, Maryland

With 700-square-feet of space, travelers love this one-bedroom, one-bath cabin in the heart of Middletown. It’s possible to check out quaint restaurants and shops while you’re here, hike the Appalachian Trail, and float on the Potomac River. The home was built in the 1890s and has been restored several times to make it especially accommodating for two people. The home comes with a TV, Wi-Fi, queen-size bed, gas grill, fire pit, and cozy kitchen. Guests have access to the whole cabin, yard, porches, shed for storage, and driveway for parking. This is a pet-friendly cabin rental in Maryland.

Amazing Riverfront Tiny House – Denton, Maryland
Credit: Airbnb.com
Relax in the hammock near the river

Amazing Riverfront Tiny House – Denton, Maryland

A cute tiny house option is this Airbnb property that can sleep three people and is right on the river. The beach is about an hour away. You’ll be in the middle of the Eastern Shore and have an opportunity to try out the tiny house experience here. The home’s dimensions are about eight feet by 16 feet. The interior offers a small kitchen, heat, A/C, queen-size bed in the loft, and full-size futon. The shower is an outdoor shower. There are free-range chickens living here, so host approval is required to bring a pet.

Newly Renovated Waterfront Getaway – Onancock Virginia
Credit: Airbnb.com
Right by the water for a quiet stay

Newly Renovated Waterfront Getaway – Onancock Virginia

Nestled on an acre on Onancock Creek, here’s a one-room guesthouse that’s quiet and newly renovated. It has a queen-size bed, full kitchen, internet, TV, and lovely views of the creek. You can check out the historic town of Onancock when you’re here and also rent kayaks in town to hang out on the creek and watch sunsets over the Chesapeake Bay. Couples looking for a quiet getaway love it here. Fish off the dock and prepare your own meals here if you like.

Boulder Ridge Cabin – Friendsville, Maryland
Credit: Vrbo.com
Perfectly tucked in and secluded

Boulder Ridge Cabin – Friendsville, Maryland

With 840 feet of square footage, this quiet cabin offers one bedroom and a bathroom to accommodate four people. It’s 15 minutes from Deep Creek Lake and Wisp Resort. The cabin comes with an equipped kitchen, laundry room, loft bedroom, shower/tub combo, and screened porch with chairs. The outside area offers a campfire area, hammock, boulders, and a trail through the woods. For sleeping, there’s a queen-size bed in the loft and a pull-out couch in the living room. Ask the host about using free passes to Deep Creek Fitness. This is a pet-friendly vacation rental listed on Vrbo.

La Casita on Harris Creek – Saint Michaels, Maryland
Credit: Airbnb.com
View peaceful sunsets just like this

La Casita on Harris Creek – Saint Michaels, Maryland

Up to three people can stay in this cottage that has one bedroom and one bath on a secluded 40-acre farm. The farm is on Harris Creek, and the guesthouse is modeled after the historic Chesapeake barns. With this rental, you’ll have a private pool, kayaks, fire pit, kitchen, Wi-Fi, and TV. The 360-degree views with wildlife and starry night skies can’t be beaten. The saltwater pool here is open between May and September. It’s fun to take the kayaks out on the water in the spring, summer, and fall from the private dock.

Getting to the Point at Cove Point Beach – Lusby, Maryland
Credit: Airbnb.com
How adorable is this white picket fence?

Getting to the Point at Cove Point Beach – Lusby, Maryland

This is a beach house where you can enjoy Cove Point Beach just 500 feet away. It does not allow kids under age eight or pets. However, for older humans, it offers an outdoor patio, fire pit, laundry machines, air conditioning, and parking in the driveway. The space accommodates four guests in two bedrooms (one with a king-size bed and the other with a queen-size bed) and two bathrooms. Wi-Fi and TV with standard cable are also provided by the host.

Northern Neck – Irvington, Virginia
Credit: Airbnb.com
Such a unique and inviting rental space

Northern Neck – Irvington, Virginia

Six people can stay at this Airbnb rental home that’s situated on two wooded acres and among the trees. It’s behind the Dog and Oyster Winery and comes with community pool access and a four-person hot tub. The home has three levels, three bedrooms, and three bathrooms. It’s close to a state park, seafood restaurants, and small towns on the water. This is an ideal spot for a couple’s getaway, girls’ or guys’ getaway, or a family retreat. The home is a pet-friendly rental.

Cottonwood Estate Farmhouse – Gloucester Point, Virginia
Credit: Airbnb.com
Live the farm life while being close to the beach

Cottonwood Estate Farmhouse – Gloucester Point, Virginia

Another option is to stay in this farmhouse cottage that’s just five miles from the beach. It’s a charming escape where you can pet cute farm animals and access fresh eggs from the chicken coop. Yorktown and Colonial Williamsburg are also close by. Book this Airbnb rental to get an escape from everyday life and have all the comforts of home, such as Wi-Fi and TV. Children love it here, and the host provides children’s items for your convenience. The bedroom has a queen-size bed, couch, floor mattress, and baby crib. With prior approval and a security deposit, you may be able to bring your dogs too.

Beautiful Open Floor Plan Waterside Home – Easton, Maryland
Credit: Vrbo.com
Beautiful Open Floor Plan Waterside Home

Beautiful Open Floor Plan Waterside Home – Easton, Maryland

Large groups of up to 10 people will be comfortable and living in luxury when they book this Vrbo rental property. The home is 5,000 square feet in size, and there are five bedrooms and three baths. Hang out by the saltwater outdoor pool, relax on the screened porch, and play a few games of ping pong. You’ll be in a unique high-elevation location that’s close to the amenities of Easton and less than 20 minutes from St. Michael’s Harbor.

Experience Complete Relaxation on the Water – Westover, Maryland
Credit: Airbnb.com
You'll love this location by the water

Experience Complete Relaxation on the Water – Westover, Maryland

Located in Westover, Maryland, here’s a historic three-story cottage on the Manokin River’s waterfront. You can access the beach next to the home and see water views from every room. Princess Anne is 10 minutes away, and there’s a grocery store 15 minutes away. The house dates back to around 1840 and is secluded in nature away from traffic and noise. It’s on a 34-acre property and about 45 minutes from public beaches in Virginia and Maryland. You’ll have your own private beach here though. It works best for five to seven adults.

The Laughing King Retreat Honeymoon Island Cottage – Cape Charles, Virginia
Credit: Airbnb.com
Experience a real organic farm

The Laughing King Retreat Honeymoon Island Cottage – Cape Charles, Virginia

It’s fun to stay in a tiny house when you’re exploring the Chesapeake Bay area of Virginia and Maryland, such as this rental home on Airbnb. It sleeps two people and is an adults-only getaway known as the Honeymoon Island Cottage. You’ll be just steps from the Chesapeake Bay here on a USDA-certified organic farm. When you’re in the charming house, you’ll also have access to a private beach, private and saltwater pool. Then you can head over to the bay’s water access point for swimming, boating, fishing, paddle boarding, and digging for clams and oysters. Pets are allowed to join you at this tiny house.

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