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Compare 54 Cottages in Chesapeake Beach with updated reviews, rates, and availability.

Waterfront nature retreat, contemporary home w/ pier by Annapolis. Pet Friendly!
10.0 out of 10, Exceptional, 1 review
Waterfront nature retreat, contemporary home w/ pier by Annapolis. Pet Friendly!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 186 reviews
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, 152 reviews
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Waterfront home with beach on the Chesapeake Dog-Friendly
9.8 out of 10, Exceptional, 20 reviews
"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 on the Chesapeake Dog-Friendly
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
10.0 out of 10, Exceptional, 32 reviews
"Lovely property."
The price is $140
$230 total
includes taxes & fees
Jun 4 - Jun 5
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
Waterfront property with private boat ramp and new dock!
Waterfront property with private boat ramp and new dock!
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
10.0 out of 10, Exceptional, 7 reviews
"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
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, 8 reviews
"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!
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, 6 reviews
"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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, 127 reviews
"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.
9.2 out of 10, Wonderful, 10 reviews
"We had a wonderful stay at this cute yellow house by the bay. It has all the comforts of home. It was perfect for family time. We would definitely stay here again."
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.
9.8 out of 10, Exceptional, 22 reviews
"Emwe enjoyed our time here, it was relaxing and close to travel around the area."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, 20 reviews
"We highly recommend Maria’s beautiful Beach cottage! House was fully equipped, beds were amazing, a lot of space and games galore! Thank you for contacting me prior to our stay with your contact information- made me feel welcomed and secure prior to our arrival. We will definitely be back when the weather gets warmer☀️🌈"
North Beach Cottage - Walk to Chesapeake Bay
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, 35 reviews
"We were in the area for an event but decided to find a nice getaway spot instead of staying in a hotel. This was a little further from the event location but well worth it! The cottage was clean and welcoming, the scenery beautiful, and overall a comfortable, quiet location."
The price is $345
$417 total
includes taxes & fees
Jul 1 - Jul 2
Cottage Located on the Patuxent River!
MEMORIAL DAY SPECIAL - 3 DAY MINIMUM 10% OFF ROOM CHARGE
MEMORIAL DAY SPECIAL - 3 DAY MINIMUM 10% OFF ROOM CHARGE
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 197 reviews
"We had our boat with us. Split out time between being on the water and going into St Michaels"
Relaxing Waterfront Cottage Near St Michaels, Maryland
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, 47 reviews
"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
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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

Bay Views |Breezy point Beach: 4BD 2BA King bed
10.0 out of 10, Exceptional, 1 review
"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 $220
$548 total
includes taxes & fees
Jun 6 - Jun 7
Bay Views |Breezy point Beach: 4BD 2BA King bed
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, 61 reviews
"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"
Mid-Century Modern and Marvelous on the Bay
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 186 reviews
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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
1,022
Accommodation
54 Cottages
Lowest Price
$140
Highest Price
$345

Frequently asked questions

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What is there to do in Chesapeake Beach near my cottage?
Chesapeake Beach has enough experiences and activities to keep you amused for weeks (or months!), starting with Breezy Point Beach. Chesapeake Beach Water Park, Bayside History Museum and Bruce Gabrielsons Surf Art Gallery and Museum are other fantastic attractions. If you’re in town for longer, Fridays Creek Winery and Franklin Point State Park will round off your itinerary nicely.

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