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Chesapeake Bay unique stays
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481 Unique places to stay in Chesapeake Bay

Top Family Unique Stays in Chesapeake Bay

Kid-friendly unique stays in Chesapeake Bay offer a perfect blend of excitement and convenience for a happy family getaway.

Blue Heron Farm Waterfront Chalet - Chesapeake Bay
10 2 reviews
Chesapeake Bay
08/23 – 08/28
$366/nighttotal: $1830 (5 )

Blue Heron Farm Waterfront Chalet

3 2
farm , Kingstown
This Chestertown, Maryland farmhouse rental, situated on a 127-acre organic farm along the Chester River, is 15 minutes from historic Chestertown and a quarter-mile from the owners' home.
The three-bedroom, two-bathroom chalet features a large wraparound deck with river views, a fully equipped kitchen, a private dock with kayaks, and access to miles of hiking trails; it sleeps six and includes a microwave, dishwasher, and air conditioning.
Pizza Friday - Chesapeake Bay
10 9 reviews
Chesapeake Bay
10/01 – 10/05
$458/nighttotal: $1832 (4 )

Pizza Friday

4 3
cabin , Piney Point
This Piney Point waterfront cottage is located less than a mile from Cardinal Gibbons Park and First District Community Park, and approximately three miles from Saint Inigoes State Forest, offering easy access to outdoor recreation.
Sleeping up to ten guests, this four-bedroom, two-bathroom home features a fully equipped kitchen, free WiFi, a fireplace, a terrace, a garden, barbecue grills, and a smart TV, perfect for family vacations.
Fisherman's Cabin On The Bay - Chesapeake Bay
8.8 26 reviews
Chesapeake Bay
07/30 – 08/05
$450/nighttotal: $2700 (6 )

Fisherman's Cabin On The Bay

3 6
cabin , Norfolk
This Norfolk cabin is located just a short block from the marina and a couple of blocks from the Chesapeake Bay's sandy beaches, offering easy access to waterfront activities and attractions. Guests consistently rate this rental as "very good," highlighting its comfortable accommodations and prime location.
The single-story home features 1450 square feet of space, comfortably accommodating up to seven guests in its three bedrooms and one bathroom. Enjoy modern amenities like a large 65" Smart TV, high-speed WiFi, a fully equipped kitchen, a charcoal grill, a fireplace, and a spacious garden perfect for relaxing and enjoying the beautiful sunsets over the Chesapeake Bay.
Kent Island Resort - Chesapeake Bay
Chesapeake Bay
08/23 – 08/28
$215/nighttotal: $1075 (5 )

Kent Island Resort

1 2
island , Stevensville
Kent Island Resort is located in Stevensville, Maryland, just a 15-minute drive from the Chesapeake Bay Bridge and Queenstown Premium Outlets. The resort offers a waterfront location with stunning views of the Chesapeake Bay, making it a perfect choice for a relaxing getaway. This charming resort features a Victorian design and offers a variety of amenities, including a swimming pool, garden, restaurant, bar, and meeting space. Guests can enjoy outdoor recreation, complimentary internet access, and convenient room service.

Best Chesapeake Bay unique accommodations with a garden

Hideaway On The Bay: Waterfront Vintage A Frame - Chesapeake Bay
9.8 252 reviews
Chesapeake Bay
08/23 – 08/28
$413/nighttotal: $2065 (5 )

Hideaway On The Bay: Waterfront Vintage A Frame

1 2
cabin , Long Beach
This charming cabin is located in Lusby, Maryland, just an hour's drive from Washington D.C., offering a peaceful escape near the Chesapeake Bay. The cabin has consistently earned excellent ratings from guests for its location, cleanliness, and overall experience.
The cozy cabin sleeps up to 5 guests and features a fully equipped kitchen with modern appliances. Enjoy kayaking, canoeing, fishing, and crabbing right from the property, relax by the fire pit, and take advantage of the nearby vineyards and nature park.
6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino - Chesapeake Bay
10 6 reviews
Chesapeake Bay
07/30 – 08/05
$1000/nighttotal: $6000 (6 )

6 Bedroom 4 Bathroom 1870 Farmhouse. Right Next To Great Wolf & Hollywood Casino

6 6
farm , Perryville
This farm stay is located in Perryville, just a short drive from the Susquehanna Museum at the Lock House and Concord Point Lighthouse, offering easy access to historical attractions and the natural beauty of the surrounding area. This spacious property provides comfortable accommodations for up to 16 guests with 6 bedrooms and 4 bathrooms, encompassing a generous 3050 square feet of living space. This rural retreat offers a variety of amenities, including a fully equipped kitchen, a fitness center, a garden, and multiple entrances for convenient access, making it an ideal destination for families and groups seeking a relaxing getaway.
Waterfront Lancaster Cabin ~ 10 Mi To Kilmarnock! - Chesapeake Bay
10 8 reviews
Chesapeake Bay
10/01 – 10/05
$387/nighttotal: $1548 (4 )

Waterfront Lancaster Cabin ~ 10 Mi To Kilmarnock!

3 3
cabin , Lancaster
This waterfront Lancaster County cottage is situated 5.1 miles from the Mary Ball Washington Museum and Library, within 12 miles of Good Luck Cellars and Compass Entertainment Complex, and near other historical sites.
The 1600-square-foot home features five bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, a terrace, a garden, and parking; enjoy outdoor grilling and a cozy fireplace.
Private 3br Farmhouse On Estate With Event Space, Horses,trails, Ponds & Orchard - Chesapeake Bay
9.4 19 reviews
Chesapeake Bay
10/01 – 10/05
$229/nighttotal: $916 (4 )

Private 3br Farmhouse On Estate With Event Space, Horses,trails, Ponds & Orchard

3 3
farm , Smyrna
This Townsend, Delaware farm stay, near Smyrna, offers easy access to Old Bohemia Wildlife Management Area and Fort DuPont State Park.
This 1,292-square-foot rural estate boasts three bedrooms, two bathrooms, sleeps eight, and includes a full kitchen, hot tub, and access to horse trails, fishing ponds, and an apple orchard.

Frequently Asked Questions about unique stays in Chesapeake Bay

  • What attractions is Baie de Chesapeake famous for?

    Chesapeake Bay is known for its beautiful beaches, like Ocean City and Assateague Island. You can also visit the Chesapeake Bay Maritime Museum in St. Michaels to learn about the region's rich maritime history.
  • What clothing or gear is recommended for the climate in Baie de Chesapeake?

    Pack light, breathable clothing for the warm and humid summers. Don't forget your swimsuit and sunscreen! In the fall and spring, you'll need layers as the weather can be unpredictable. And in the winter, pack warm clothes and a jacket.
  • What are the best ways to travel to Baie de Chesapeake eco-consciously?

    To travel eco-consciously, consider taking the train to Baltimore or Washington, D.C., then renting a car. You can also explore the Bay by bike or kayak, which are great ways to enjoy the scenery and get some exercise.
  • Which neigbourhood offers the best unique stays in Baie de Chesapeake?

    St. Michaels is a great place to find unique stays. The town has a variety of charming inns and bed and breakfasts, as well as waterfront cottages and vacation rentals.
  • What should you know about unique stays in Baie de Chesapeake before booking?

    Before booking a unique stay, check the reviews and make sure it's the right fit for you. Some unique stays may be more remote or have limited amenities, so it's important to do your research.

Destinations nearby

Find the Best Unique Stays with a Hot Tub in Chesapeake Bay

These unique stays in Chesapeake Bay feature private hot tubs, perfect for a private soak after a day by the water.

Lakefront Cabin Near Solomons Island W/ Hot Tub - Chesapeake Bay
Chesapeake Bay
10/01 – 10/05
$615/nighttotal: $2460 (4 )

Lakefront Cabin Near Solomons Island W/ Hot Tub

3 3
cabin , Chesapeake Ranch Estates
This lakefront vacation home in Lusby, Chesapeake Ranch Estates, offers direct beach access and lake views, located 5.5 miles from Annmarie Garden and 6.4 miles from Calvert Marine Museum.
This three-bedroom, two-bathroom residence spans 1860 square feet, accommodating up to 23 guests with a fully equipped kitchen, hot tub, private patio, and free Wi-Fi.
Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay! - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$435/nighttotal: $3045 (7 )

Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay!

2 2
cabin , Charlestown
This log lodge in Charlestown is situated 30 miles from the Old Dutch House in North East, 19 miles from Dayett Station, and 20 miles from the Tennis Court.
This 400-square-foot vacation home offers 2 bedrooms, 1 bathroom, and accommodates up to 15 guests with amenities including a kitchenette, refrigerator, microwave, air conditioning, a hot tub, garden, fitness center, tennis court, and parking.

Best pet friendly Chesapeake Bay unique stays

Among the 481 accommodations in Chesapeake Bay, here are the 4 best pet friendly unique accommodations

Woodsy + Secluded! Amish Country Retreat In Hartly - Chesapeake Bay
Chesapeake Bay
08/23 – 08/28
$183/nighttotal: $915 (5 )

Woodsy + Secluded! Amish Country Retreat In Hartly

1 2
apartment , Hartly
This apartment in Hartly, Kent County, is located near local Amish markets and within 17 miles of Blackbird State Forest and Bombay Hook National Wildlife Refuge.
This 320 sq ft studio dwelling accommodates two guests and features a kitchenette with a fridge and microwave, air conditioning, parking, and a front porch, with the option for dog-friendly stays for an additional fee.
Sailboat Experience In Annapolis - Chesapeake Bay
10 1 review
Chesapeake Bay
08/23 – 08/28
$251/nighttotal: $1255 (5 )

Sailboat Experience In Annapolis

1 2
houseboat , Annapolis
This houseboat offers a waterfront location in Annapolis, placing you near the Kunta Kinte Alex Haley Memorial and Thurgood Marshall Memorial, and within 2 miles of Jonas Green State Park and Sandy Point State Park.
This 130-square-foot vessel accommodates two guests, featuring one bedroom, one bathroom, air conditioning, internet, and a kitchen, providing a unique camping-like experience on the water with opportunities for sailing.
The Whispering Rafters Tiny Home - Chesapeake Bay
10 1 review
Chesapeake Bay
08/29 – 09/05
$281/nighttotal: $1967 (7 )

The Whispering Rafters Tiny Home

1 2
farm , Bel Air South
This historical farm stay in Bel Air offers a unique lodging experience within a restored 1760s enslaved quarters and chicken coop, providing a palpable connection to centuries of American history.
This sanctuary for two features air conditioning and internet, accommodates two guests, and is located a short drive from Gunpowder Falls State Park and Susquehanna State Park, with the Havre de Grace Maritime Museum also nearby.
Family Retreat At Lansdowne Manor - Chesapeake Bay
10 12 reviews
Chesapeake Bay
07/30 – 08/05
$752/nighttotal: $4512 (6 )

Family Retreat At Lansdowne Manor

4 6
farm , Centreville
This Centreville farm stay, a 3,500-square-foot rural rental, is conveniently located within 9-12 miles of attractions like the Hazel Miner Monument, Tuckahoe State Park, Adkins Arboretum, Church Hill Theatre, and Cassinelli Winery and Vineyards.
The four-bedroom, three-bathroom house sleeps eight and offers amenities including air conditioning, a full kitchen with dishwasher, internet access, pet-friendliness, and ample parking.

Browse Waterfront Unique Stays in Chesapeake Bay

Plan an eccentric holiday at coastal unique stays in Chesapeake Bay, situated short distances from regional beach-town boardwalks.

Watch Deer From A Farm Cottage - Chesapeake Bay
10 6 reviews
Chesapeake Bay
10/01 – 10/05
$326/nighttotal: $1304 (4 )

Watch Deer From A Farm Cottage

3 3
farm , Bel Air South

Explore Unusual Accommodations with Swimming Pool in Chesapeake Bay

Every unique stay near the water in Chesapeake Bay includes a pool to complement your time by the shore.

Remarkable Waterfront Property On 270 Acres - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$2198/nighttotal: $15386 (7 )

Remarkable Waterfront Property On 270 Acres

5 2
farm , Madison
Sailboat Experience In Annapolis - Chesapeake Bay
8.8 5 reviews
Chesapeake Bay
08/29 – 09/05
$222/nighttotal: $1554 (7 )

Sailboat Experience In Annapolis

1 2
boat , Annapolis
Luxe Houseboat: Breathtaking Skyline 360 Views - Chesapeake Bay
10 24 reviews
Chesapeake Bay
10/01 – 10/05
$968/nighttotal: $3872 (4 )

Luxe Houseboat: Breathtaking Skyline 360 Views

1 3
houseboat , Baltimore
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