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Chesapeake Bay unique stays
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354 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.

A Little Slice Of Heaven On The Choptank River. - Chesapeake Bay
10 31 reviews

A Little Slice Of Heaven On The Choptank River.

chalet, Cambridge
This charming cottage is located in East New Market, just across from the Hyatt Resort and a short distance from downtown Cambridge's attractions and restaurants. The chalet has received excellent user ratings, making it a popular choice for travelers.
The cottage features two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy access to a private waterfront location with a terrace, a garden, and a kitchen equipped with a fridge and microwave, plus amenities like air conditioning.
The Tilghman Island Inn - Chesapeake Bay
9.3 76 reviews

The Tilghman Island Inn

island, Tilghman Island
Tilghman Island Inn is situated on Tilghman Island, a 5-minute walk from the Chesapeake Bay and Tilghman Island Marina, and 0.2 miles (approximately 1,056 feet) from Chesapeake Bay (North).
This inn offers complimentary Wi-Fi, on-site parking, a restaurant, a bar, a seasonal outdoor pool, and bicycle rentals, with grab-and-go breakfast available daily.
Fisherman's Cabin On The Bay - Chesapeake Bay
8.8 26 reviews

Fisherman's Cabin On The Bay

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.
La Cabaña - Chesapeake Bay
9.8 79 reviews

La Cabaña

cabin, Nanticoke Acres
This Nanticoke Acres cabin rental offers a secluded wooded setting near a pier, providing peace and quiet for guests.
The one-bedroom, one-bathroom cottage sleeps four, features a fully equipped kitchen (fridge, microwave), air conditioning, laundry facilities, kayaks, fishing equipment, and a first-aid kit; plus, it includes internet access and parking.

Best Chesapeake Bay unique accommodations with a garden

Pizza Friday - Chesapeake Bay
10 9 reviews

Pizza Friday

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.
Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields - Chesapeake Bay
10 9 reviews

Freshly Renovated C1900 Farmhouse In Plainview Surrounded By Crop Fields

farm, West Point
This Buena Vista farmhouse rental in Middlesex County sits between West Point and Gloucester, providing easy access to the Middlesex County Museum and Gloucester Museum of History.
This 3000-square-foot property boasts four bedrooms, three bathrooms, and accommodates up to ten guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a terrace, air conditioning, and a lovely garden.
Sunset Point Farm - Gracious Country Farm On The Chesapeake Bay - 75 Acres - Chesapeake Bay
9.6 31 reviews

Sunset Point Farm - Gracious Country Farm On The Chesapeake Bay - 75 Acres

manor house, Boston
This luxurious 2,500-square-foot waterfront farm stay, near Exmore, Virginia, offers a tranquil escape from Boston, located within 12 miles of Exmore Town Park, Northampton Shopping Center, and The Blue Crow Antique Mall.
This four-bedroom, three-bathroom vacation rental accommodates up to ten guests and features a fully equipped kitchen, air conditioning, a terrace, a garden, concierge service, parking, and access to nearby golf and a community college, plus on-site barbecue grills.
2-bedroom Lake-house With A Magnificent View - Chesapeake Bay
9.6 203 reviews

2-bedroom Lake-house With A Magnificent View

cabin, Drum Point
This Drum Point cabin is located just a short walk from the bay beach, offering stunning sunrise and sunset views. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The cabin comfortably sleeps six guests in its two bedrooms and two bathrooms. You'll find a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, a peaceful garden, and a relaxing hot tub, all perfect for a memorable stay.

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.

Popular destinations

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.

Cozy Modern Chesapeake Bay Home - Chesapeake Bay
9.7 427 reviews

Cozy Modern Chesapeake Bay Home

bungalow, Deale
This Deale bungalow sits right on the Chesapeake Bay, offering stunning sunset views and a relaxed atmosphere. It's highly rated by previous guests for its cleanliness, location, and overall experience.
The two-bedroom home comfortably sleeps four guests and features a full kitchen, a private dock, and a jacuzzi. Enjoy kayaking, fresh seafood, and the beauty of the Chesapeake Bay right from your doorstep.
Lakefront Cabin Near Solomons Island W/ Hot Tub - Chesapeake Bay
No reviews

Lakefront Cabin Near Solomons Island W/ Hot Tub

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
No reviews

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

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.
Loveboat, Where Love Meets The Waves. - Chesapeake Bay
10 8 reviews

Loveboat, Where Love Meets The Waves.

barge, Cambridge
This unique waterfront accommodation in Cambridge, Maryland, offers a private escape with convenient access to dining and local attractions, including Portside Seafood Restaurant (a 3-minute walk), Sailwinds Park (a 15-minute walk), and the Choptank River Lighthouse (a 15-minute walk).
This one-bedroom houseboat accommodates up to three guests and features a full bathroom, a kitchen with a fridge and microwave, air conditioning, a jacuzzi, and a private porch with water views, allowing for a comfortable and relaxing stay.

Best pet friendly Chesapeake Bay unique stays

Among the 354 accommodations in Chesapeake Bay, here are the 4 best pet friendly unique accommodations

Outrange At Blue Heron Farm. Pet Friendly Cabin At Waterfront Farm! - Chesapeake Bay
9.8 25 reviews

Outrange At Blue Heron Farm. Pet Friendly Cabin At Waterfront Farm!

cabin, Kingstown
Outrange cabin, a waterfront retreat near Chestertown, Maryland, offers a private dock and Chester River views on a 127-acre organic farm, just 15 minutes from historic Chestertown.
This two-bedroom, one-bathroom cottage sleeps six, features a microwave and dishwasher, air conditioning, internet access, and allows pets; nearby attractions include Tilmon's Island Winery and Rolphs Wharf Marina, with opportunities for birdwatching and walking trails.
Multi-home Waterfront Eastern Shore Retreat With 80+ Acres To Yourself - Chesapeake Bay
10 1 review

Multi-home Waterfront Eastern Shore Retreat With 80+ Acres To Yourself

manor house, Madison
This waterfront farm stay in Cambridge, Maryland, offers direct water access and is a short drive from downtown attractions like the Richardson Maritime Museum and the Harriet Tubman Museum. This 7-bedroom, 4-bathroom house accommodates up to 18 guests and features private waterfront access for fishing and crabbing, along with air conditioning and internet.
Private 3br Farmhouse On Estate With Event Space, Horses,trails, Ponds & Orchard - Chesapeake Bay
9.4 23 reviews

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

manor house, 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.
"Elderberries" Chesapeake Bayfront Cottage - Chesapeake Bay
9.7 38 reviews

"Elderberries" Chesapeake Bayfront Cottage

cabin, Kilmarnock
"The Elderberries" is located on the Chesapeake Bay in Kilmarnock, offering stunning waterfront views and easy access to kayaking and fishing. It has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom, two-bathroom cottage comfortably sleeps four guests. It features a well-equipped kitchen, a screened-in porch, a hammock swing, a fire pit, and two kayaks for exploring the bay.

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.

El  Camino - Chesapeake Bay
10 58 reviews

El Camino

cabin, Piney Point

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.

Luxe Houseboat: Breathtaking Skyline 360 Views - Chesapeake Bay
10 26 reviews

Luxe Houseboat: Breathtaking Skyline 360 Views

houseboat, Baltimore
Coles Point Marina - Chesapeake Bay
No reviews

Coles Point Marina

cabin, Montross
Luxe Houseboat With Epic 360 Views Of Baltimore Harbor - Chesapeake Bay
10 15 reviews

Luxe Houseboat With Epic 360 Views Of Baltimore Harbor

houseboat, Baltimore
Maryland Vacation Rental W/ Private Pool & Dock - Chesapeake Bay
9.4 16 reviews

Maryland Vacation Rental W/ Private Pool & Dock

cabin, Long Beach
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