Search Eastern Shore Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Eastern Shore Cottages

Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (89)
"Lovely visit. I have a 1 and 3 year old. They loved the water and meeting the llama. The room set up is confusing in the listing. Its 3 bedrooms with 2person beds and a forth bedroom w a 1person bed."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
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
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
10.0 out of 10, Exceptional, (3)
"Loved the tiny house and it’s located close to everything. Check in was easy and we loved the layout."
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
Save an average of 15% on thousands of hotels when you're signed in
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
10.0 out of 10, Exceptional, (13)
"My boyfriend and I were in OCMD for Oceans Calling music festival and wanted to stay somewhere quieter. This cottage was perfect! It was exactly as pictured and in a quiet, safe neighborhood. Parking was a breeze. Our hosts were communicative and so nice. We would definitely stay again!"
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
Private Carriage House Retreat on a 33 Acre Historic Working Estate
10.0 out of 10, Exceptional, (8)
"It was me, my son and my sister staying. The grounds were beautiful, and we fed the goats too! It was late season, so no pool or any relaxing outdoors. Brrr. Traffic is light in the area so it was easy to get in a 2+ mile walk and see the local neighborhoods. As it was mentioned in the listing (but not obvious in the photos), you have to walk through the bunk room to get to the master bedroom, and the door to the upstairs bath doesn't offer total privacy. No place is perfect, and we would...
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
9.8 out of 10, Exceptional, (14)
"The place was amazing and in a perfect location. I would go back again!"
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, (85)
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
Cottage downtown on a quiet street
9.8 out of 10, Exceptional, (59)
"My husband and I visited St. Michael’s for our 20th anniversary. This cottage was exactly what we were looking for. It is central located so we were able to walk everywhere. The cottage had everything you would need to have a fabulous stay. The town is charming and the people are just as charming and welcoming."
Cottage downtown on a quiet street
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
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!
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
9.6 out of 10, Exceptional, (15)
"Beautiful river views. Really clean and nicely maintained property. I liked the location which was close to Chesapeake City and reasonable to Elk Neck. We had five and it held us well. It is on the small side but with great outdoor spaces . Hot tub was a nice addition. The host was easy to get a hold of. Wouldn't hesitate to go again"
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (125)
"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
Shore Point Cottages
3.0 star property
9.0 out of 10, Wonderful, (46)
"Clean, safe, homes were close together but overall it was great"
Shore Point Cottages
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
8.6 out of 10, Excellent, (4)
"Overall, we all enjoyed our stay. I gave full stars as the property was beautiful and brand new. Some things I had concerns with was initially getting to the property. When putting in the address, our gps took us down some random road which was only down the street from the actual property. Also, when showering, (the shower was very modern and beautiful) the shower door would slide open and not stay shut for multiple guests that took showers. It also would have been nice to know exactly how to...
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
8.4 out of 10, Very good, (41)
"clean, great location, well equipped cottage, nice park across street for dogs."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
8.4 out of 10, Very good, (11)
"Was a great place for our family vacation. Even though it was right off of Coastal Highway the noise from the road was not too bad especially with the AC units running. Very close to the beach & perfect for walking our dog. The cottage is bigger inside than it looks. Didn't particularly care for the shared laundry but, we made it work - only had to do one load anyway. Looking for some privacy away from condo life, we recommend this little cottage."
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
Deluxe Cottage - 2 Bedroom Cabin 3 - Deluxe Cottage with two bedrooms.
8.0 out of 10, Very good, (2)
"the blind in the living room area was missing , leaving us feel exposed at night . i made two calls and left a message , no reply . the numbers on the cabins did not match up with the listing . we were supposed to be in cottage 3 the email gave us a different number , a little confusing ."
Deluxe Cottage - 2 Bedroom Cabin 3 - Deluxe Cottage with two bedrooms.
A pair of bay view cottages with cable & free WiFi - walk 2 blocks to the beach
7.6 out of 10, Good, (9)
"This Stay was very disappointing. From the check-in process, where the property management company made you come in person to get a blank envelope since the door had a keycode, to the ants throughout the kitchen and bathroom there were some minor annoyances but there were also some major issues. 1) in unit B one of the bedrooms did not have heat. If it was summer this may not be an issue but when it is getting down into the 30s at night that means its not a usable room. 2) The bunk beds...
A pair of bay view cottages with cable & free WiFi - walk 2 blocks to the beach
Deluxe Cottage - 2 Bedroom Cabin 2 - Deluxe Cottage with two bedrooms.
Deluxe Cottage - 2 Bedroom Cabin 2 - Deluxe Cottage with two bedrooms.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Don't see what you're looking for?
See all available properties in Eastern Shore
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 Eastern Shore

Beautiful suite between bay & beach w/ access to pool, private W/D, & central AC
9.8 out of 10, Exceptional, (7)
"clean - updated - fabulous location!"
Beautiful suite between bay & beach w/ access to pool, private W/D, & central AC
Shore Point Cottages
3.0 star property
9.0 out of 10, Wonderful, (46)
"Clean, safe, homes were close together but overall it was great"
Shore Point Cottages
Coconut Malorie Resort Ocean City a Ramada by Wyndham
3.0 star property
7.4 out of 10, Good, (1176)
"Staff was extremely kind and helpful. We will look to stay here during the season and will stay here again for cheerleading competition in the future"
Coconut Malorie Resort Ocean City a Ramada by Wyndham
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.

Eastern Shore Cottages information

Number of reviews
769
Accommodation
23 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do holiday cottages in Eastern Shore cost?
Holiday cottages in Eastern Shore range between and per night. These retreats offer a chance to get in tune with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many holiday cottages are there in Eastern Shore?
Eastern Shore has 23 holiday cottages to choose from. Enter your travel dates and destination and lock in your dream getaway today.
Why book your cottage in Eastern Shore with Expedia?
Reserving a cottage in Eastern Shore is as easy as entering your travel dates and picking an ideal place for a getaway in nature. From high-end retreats to low-cost stays and holiday cottages that come with perks like a pool, Expedia has something for all tastes and styles. As for the best offers around? We’ve got them as well!
How can I find cheap cottages in Eastern Shore?
Expedia is here to help you track down cheap cottages in Eastern Shore. To discover your perfect stay in just a few clicks, try out the filter tool to refine your search results by amenities, star rating and budget.

Eastern Shore Hotel Reviews
Expedia verified reviews