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Browse Select Chesapeake Beach Cottages

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (188)
"We loved our stay at the cottage. The weather was absolutely beautiful which meant every waking hour was spent outside on the deck of the cottage or at any one of several nature parks nearby. The serenity was just what we needed: mornings spent gazing at the water; evenings spent watching beautiful sunsets from the deck and/or pier, staying up well into the nighttime by the fire pit. The deer visited the yard multiple times daily adding to the serenity of the property. The only thing lacking was...
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (106)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Waterfront property with private boat ramp and new dock!
Outdoor dining
Waterfront property with private boat ramp and new dock!
10.0 out of 10, Exceptional, (2)
"Fun stay in an older refurbished home. All of the amenities one could need with a great water front area"
Waterfront property with private boat ramp and new dock!
Waterfront home with beach mins to downtown boat or car Dog-Friendly
Property grounds
Waterfront home with beach mins to downtown boat or car Dog-Friendly
9.8 out of 10, Exceptional, (20)
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Waterfront home with beach mins to downtown boat or car Dog-Friendly
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Beach nearby
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
10.0 out of 10, Exceptional, (7)
"We loved this property! Walk to the little local beach and a short drive to parks, larger beaches and museums. Kelsey is a great host and the house was perfect for us and the kids. Would book again."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (155)
"Very nice home! It was decorated with many antiques and gave you a feeling of another time but with all the modern amenities for a wonderful time."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (127)
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Cozy Cottage with access to and partially obstructed views of the bay.
Beach nearby
Cozy Cottage with access to and partially obstructed views of the bay.
9.4 out of 10, Exceptional, (12)
"This was a great little getaway! The property was very accurate to the listing, and everything was very clean and tidy. We cooked a bit at the house and it had all the pots/pans/utensils we needed. The beach across the street is quite nice, and it's a short drive to Calvert Cliffs State Park. Would definitely recommend this VRBO!"
Cozy Cottage with access to and partially obstructed views of the bay.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (24)
"Appreciated the lovely waterfront location, independence , nice filtered water tap for drinking and coffee. Especially enjoyed meeting owner, delightful visit."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Artist, writer & creative minds stay where inspiration is free & serenity lives
Property grounds
Artist, writer & creative minds stay where inspiration is free & serenity lives
Artist, writer & creative minds stay where inspiration is free & serenity lives
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Beach
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (109)
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (198)
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
Outdoor pool
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
10.0 out of 10, Exceptional, (34)
"Picked this property due to the location outside of the “city” and loved the rural location. The cottage fit our needs perfectly. Diana was very friendly and a wonderful host. The location was very peaceful."
The price is £183
per night
23 Jun - 24 Jun
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (1)
"This was an amazing property. Very clean and very cute and cozy. Beautiful property. The owners were fantastic. Very responsive and caring. Loved it! Would definitely return."
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Property grounds
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (3)
"Beautiful location, great views, beautiful sun rises, view of working watermen Dogwood Harbour. Owner met us at the property with a bottle of wine — very friendly. Tilghman Island is a quaint and beautiful gem."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, stovetop, dishwasher
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (9)
"This location was perfect for our trip for a wedding. Being only a three minute walk from the rehearsal, ceremony, and reception was absolutely perfect. Being close to the deli/market as well came in handy. The house was clean and welcoming. Overall I would absolutely stay here again."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Eastern Shore Waterside Cottage Near St. Michaels
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (6)
"Great property, extremely clean and exactly as pictured on listing. Host was responsive and check in and check out was a breeze. Would recommend if you’re looking for a quiet weekend away at the Eastern shore!"
Eastern Shore Waterside Cottage Near St. Michaels
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Property grounds
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
8.4 out of 10, Very good, (8)
"The property had everything we needed. It was clean and in a nice quiet area. Will go back again."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
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See all available properties in Chesapeake Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chesapeake Beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
10.0 out of 10, Exceptional, (1)
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
The price is £736
per night
20 Jul - 21 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (62)
"The house is a perfect retreat! I watched the sunrise from my bedroom and porch with my coffee each day of our stay. My parents live just 2 doors down. I have been coming to this neighborhood since the 70's. I still love hunting for fossils on the beach. Thank you for allowing us to book this spot!"
Mid-Century Modern and Marvelous on the Bay
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chesapeake Beach Cottages information

Number of reviews
997
Accommodation
55 Cottages
Lowest Price
£183
Highest Price
£183

Frequently asked questions

Why book your cottage in Chesapeake Beach with Expedia?
Expedia has some great holiday cottages in Chesapeake Beach, so get set for an unforgettable stay on nature’s doorstep. If you have a budget, choose how much you want to spend and the preferred star rating of your property. Or, try out our filters to search for holiday cottages with free WiFi or a pool. We’ll help you find the right digs whatever your trip looks like.
How can I find cheap cottages in Chesapeake Beach?
The quickest way to compare cheap cottages in Chesapeake Beach is with Expedia’s useful filter tool. Narrow your search results by star rating, budget and amenities to discover awesome bargains in a couple of clicks.
What is there to do in Chesapeake Beach near my cottage?
There are lots of fabulous things that’ll fill up your itinerary in Chesapeake Beach. Discover top attractions like Chesapeake Beach Water Park, Breezy Point Beach and Bayside History Museum. Fridays Creek Winery, Franklin Point State Park and Bruce Gabrielson’s Surf Art Gallery and Museum are other must-see’s.

Chesapeake Beach Hotel Reviews
Expedia verified reviews

St Michaels Inn

St Michaels Inn

5/5 Excellent
"We love it"
A verified traveller stayed at St Michaels Inn
Posted 2 days ago
St Michaels Inn