Photo by Ronanne Vinson

Search Chesapeake Beach Cottages

Most properties are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

Compare 46 Cottages in Chesapeake Beach with updated reviews, rates, and availability.

Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"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
Fridge, microwave, stovetop, dishwasher
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (8)
"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!
Outdoor pool
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
10.0 out of 10, Exceptional, (32)
"Lovely property."
The price is $140
$230 total
includes taxes & fees
May 19 - May 20
Relaxing and peaceful guest house close to beach towns and DC. Lotsa amenities.
Save an average of 15% on thousands of hotels when you're signed in
Property grounds
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (103)
"Really enjoyed the house and it’s location, perfect for a couples weekend!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (126)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Beach nearby
Cozy Cottage with access to and partially obstructed views of the bay.
9.2 out of 10, Wonderful, (10)
"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.
Interior
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (20)
"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
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (195)
"We enjoyed our stay very much. It was lovely to sit either on the screened in porch or in the living room and look out onto the water. It happened to be chilly & rainy during our stay but with views of the water, we didn’t even mind that."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"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
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
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (5)
"We loved Waterside Cottage. It was so quite & the crabbing was wonderful which is what we were looking for. Topher was wonderful to work with both before we arrived & on the day of arrival. My husband is already asking if we can book it again next year."
Eastern Shore Waterside Cottage Near St. Michaels
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!
Exterior
Charming Cottage by the Chesapeake Bay - 1 block from private Calvert beach
9.0 out of 10, Wonderful, (8)
"Went for vacation and to find shark teeth"
Charming Cottage by the Chesapeake Bay - 1 block from private Calvert beach
Outdoor dining
Waterfront property with private boat ramp and new dock!
Waterfront property with private boat ramp and new dock!
Sun loungers
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (35)
"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 $295
$354 total
includes taxes & fees
May 17 - May 18
Cottage Located on the Patuxent River!
Interior
Family-friendly Chesapeake Beach House With Deck!
3.0 star property
Family-friendly Chesapeake Beach House With Deck!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (1)
"Thank you so much for our wonderful time at the Point of View. We were so comfortable we didn’t want to ever leave – it was clean and comfortable. The home feels brand new because it has been renovated very recently. The furniture and kitchen are brand new and perfect for the space. The water views are incredible in every direction – we watched stunning sunrises (and moon rises!) to the east, we watched the awesome sunsets to the west and thoroughly enjoyed watching all the action in Dogwood...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Fridge, microwave, oven, stovetop
Relax in our cottage within walking distance of Herrington on the Bay events.
9.6 out of 10, Exceptional, (88)
"Perfect for 6 adults for a weekend gathering. Lots of space, and a nice outdoor area"
Relax in our cottage within walking distance of Herrington on the Bay events.
Don't see what you're looking for?
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

Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (60)
"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"
Mid-Century Modern and Marvelous on the Bay
Pool
Bay Views |Breezy point Beach: 4BD 2BA King bed
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 $170
$485 total
includes taxes & fees
May 21 - May 22
Bay Views |Breezy point Beach: 4BD 2BA King bed
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"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
1,075
Accommodation
46 Cottages
Lowest Price
$140
Highest Price
$295

Frequently asked questions

Why book your cottage in Chesapeake Beach with Expedia?
We think that a vacation should be a piece of cake, so if you’re in search of cottages in Chesapeake Beach at a competitive rate, Expedia is here to help. Save money and opt for a thrifty option surrounded by wilderness, or splurge on a luxury cottage to pamper your favorite people.
How can I find cheap cottages in Chesapeake Beach?
With Expedia’s user-friendly filter tool, booking cheap cottages in Chesapeake Beach has never been simpler. To discover accommodations that’ll make your hip pocket happy, narrow your search results by amenities, star rating and budget.
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.

Recent reviews of Chesapeake Beach hotels
Expedia verified reviews