Search Eastern Shore Cottage Rentals

    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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 24 Cottages in Eastern Shore with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
cottage, community pool, playground, boating, crabbing kayaking and fishing!!!
10.0 out of 10, Exceptional, (2)
"Wonderful Location and proximity to Ocean City!Quiet,quaint ocean cottages on bayside.Great for walks in neighborhood,esplly with our doggies.Plenty trails close by.Highly recommend Isle of Wight Park(is on the way over or back from OC)Nice cozy place and beds. Sunroom toasty and warm.There is heater,AC unit on both sides.Stayed plenty warm enough on cool Fall nights.All amenities as home,kitchen ,fridge microwave, stocked pans,silverware and items.(We had brought our usual paper plates,bowls...
cottage, community pool, playground, boating, crabbing kayaking and fishing!!!
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (53)
"Had a wonderful time really enjoyed the use of the dock the house was perfect had everything you could of possibly needed definitely will be back!"
Waterfront Cottage in Beautiful Hoopers Island
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
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
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
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
Pool | Outdoor pool
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
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
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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (127)
"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
Property grounds
Comfortable cottage in gated community, 5 mins to OC and Assateague
9.6 out of 10, Exceptional, (12)
"Spent a long weekend at this property and had a wonderful time. Good food in Berlin. Very close to the Assateague National Seashore, and Ocean City. The weather wasn't the greatest but we weren't expecting warm and sunny in the middle of February. Mostly it was just a nice relaxing stay."
The price is ￥35,021
per night
May 29 - May 30
Comfortable cottage in gated community, 5 mins to OC and Assateague
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (104)
"Loved this historic house! Perfect location, peaceful neighborhood and walking distance to entire town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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"
The price is ￥46,100
per night
Jun 2 - Jun 3
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
Fridge, microwave, stovetop, dishwasher
Shore Point Cottages
3.0 star property
9.2 out of 10, Wonderful, (56)
"Beautiful space! We’ll stay again!"
Shore Point Cottages
Fridge, microwave, oven, stovetop
Cozy Coastal Cottage Ocean Pines
9.0 out of 10, Wonderful, (15)
"Good neighborhood. Communication with host was great! Nice OC home!! Would stay again."
Cozy Coastal Cottage Ocean Pines
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
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.
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
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
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

Property grounds
Near it all OC beaches,Assateague island.Family-friendly white horse park
10.0 out of 10, Exceptional, (11)
"We had such a comfortable stay! Thoughtful hosts, adorable home in a safe and quiet area. We would definitely recommend and stay here again! Thank you so much!"
Near it all OC beaches,Assateague island.Family-friendly white horse park
Fridge, microwave, stovetop, dishwasher
Shore Point Cottages
3.0 star property
9.2 out of 10, Wonderful, (56)
"Beautiful space! We’ll stay again!"
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, (1180)
"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
691
Accommodation
24 Cottages
Lowest Price
￥46,100
Highest Price
￥46,100

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
Spring break
"Enjoyed my stay. The view, the floor I was on. Front desk was pleasant. "
A verified traveler stayed at Holiday Inn & Suites Ocean City, an IHG Hotel
Posted 18 hours ago
Holiday Inn & Suites Ocean City, an IHG Hotel