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Compare 23 Cottages in Eastern Shore with updated reviews, rates, and availability.

Fridge, microwave, stovetop, dishwasher
Shore Point Cottages
3.0 star property
9.2 out of 10, Wonderful, (48)
"This was our 3rd stay at Shore Point. We love the quaint community feel of it. The cottages are cute and have plenty of room. Our only complaint is that the bedspreads were dirty the 1st time we came, so we have been bringing our own."
Shore Point Cottages
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (52)
"A small house, well situated overlooking the waterfront, with a private pier. House interior was very clean and tidy!"
Waterfront Cottage in Beautiful Hoopers Island
Private kitchen
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.
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Property grounds
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
Property grounds
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior
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.
Dining
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
Property grounds
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
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!
Exterior
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
Beach nearby
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
Fridge, microwave, oven, stovetop
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
Property grounds
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
Interior
Chesapeake Romantic Waterfront Home with Private Pool
8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
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
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
Beach nearby, beach towels
-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
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
Interior
Charming Salisbury Getaway w/ Grill & Fire Pit!
3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!
Lake
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
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

Basic Apartment, 2 Bedrooms, Non Smoking | Private kitchen
Majestic Hotel & Apartments
3.0 star property
6.4 out of 10, (68)
"We stayed in one of the majestic apartments. I liked how it was an apartment, but it wasn't like dealing with a rental company. It was dealing with a hotel company. It was very simple and easy to get set up. We were lucky enough to get one of the apartments that was detached a block away. So it was a lot more quiet. The property is definitely dated, if you're looking for some modern place this is not it. With that being said though it was very clean. Which I'm not going there to stay in a hotel...
The price is $55
$61 total
includes taxes & fees
May 30 - May 31
Majestic Hotel & Apartments
Fridge, microwave, stovetop, dishwasher
Shore Point Cottages
3.0 star property
9.2 out of 10, Wonderful, (48)
"This was our 3rd stay at Shore Point. We love the quaint community feel of it. The cottages are cute and have plenty of room. Our only complaint is that the bedspreads were dirty the 1st time we came, so we have been bringing our own."
Shore Point Cottages
Studio, 1 King Bed, Non Smoking | Balcony
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
760
Accommodation
23 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in Eastern Shore cost?
Cottages in Eastern Shore range between and per night. These stays offer a chance to soak up nature’s beauty — 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.
What are the best cottages in Eastern Shore?
Slide right into vacation mode and slow things down in one of Eastern Shore’s multiple cottages. With a total average guest review rating of 9.4, there’s something for everyone’s budget and taste. Many visitors to Ocean City prefer a stay at Frontier Town Campground, a 2-star cottage retreat with a barbecue grill and a swimming pool. Another top-rated option in this much-visited destination is 103 79th Street 3 Bedroom Cottage. This 3-star escape comes with a patio and free self parking.
How many cottages are there in Eastern Shore?
You can select from 23 cottages in Eastern Shore. Whether you’re traveling with the entire family, as a duo or with a group of workmates, Expedia will help you find the perfect place.
Are there any family-friendly cottages in Eastern Shore?
There are family-friendly cottages in destinations across Eastern Shore, including Ocean City. Frontier Town Campground is one option that’ll suit your style in this renowned city. It has a 2-star rating and handy amenities like a swimming pool and a playground. Also take a look at 103 79th Street 3 Bedroom Cottage. With a nearby beach and pet-friendly facilities, this 3-star cottage in Ocean City will make your crew feel relaxed and welcome. Once you’ve settled in, it’s time to explore Ocean City. Look forward to making memories together at family-friendly attractions such as Ocean City Beach and Jolly Roger Amusement Park.
Why book your cottage in Eastern Shore with Expedia?
Booking a cottage in Eastern Shore is as simple as deciding on your travel dates and choosing an ideal place for a getaway in the outdoors. From luxurious retreats to affordable properties and cottages that feature amenities like laundry facilities, Expedia has something for all traveler tastes. As for epic deals? We’ve got your back!
How can I find cheap cottages in Eastern Shore?
Expedia can help you track down cheap cottages in Eastern Shore. To lock in a fantastic stay in a few quick clicks, try out the filter tool to tailor your search results by star rating, amenities and budget.
What is there to do in Eastern Shore near my cottage?
The most important travel accessory for your Eastern Shore getaway is a good itinerary! Ocean City Beach, Seacrets Distilling Company and Trimpers Rides are some of the top sights if you’re off to Ocean City. Berlin also has plenty of big-name attractions, such as Globe Theater. Eager to explore more? Check out Main Street Berlin and The Bay Club too.

Recent reviews of Eastern Shore hotels
Expedia verified reviews

Holiday Inn & Suites Ocean City, an IHG Hotel

Holiday Inn & Suites Ocean City, an IHG Hotel

5/5 Excellent
"Amazing hotel!! The staff and restaurant was absolutely fantastic! A definite must-stay when in O.C! "
A verified traveler stayed at Holiday Inn & Suites Ocean City, an IHG Hotel
Posted 12 hours ago
Holiday Inn & Suites Ocean City, an IHG Hotel