Search Eastern Shore Cottage Rentals from CA $141

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Browse Select Eastern Shore Cottages

Shore Point Cottages
Fridge, microwave, stovetop, dishwasher
Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, (199)
"We had an amazing time we even extended our stay . The management I believe her name was Erin was absolutely amazing , she was friendly and helpful . The property was so clean and so convienent. We will be back great place to stay ."
The price is CA $154
CA $216 total
includes taxes & fees
Nov 18 - Nov 19
Shore Point Cottages
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (63)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (134)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
Exterior
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
10.0 out of 10, Exceptional, (6)
"Fresh and clean , new gated community , except for street light at first cabin and they need black out blinds on windows, was to bright to try and sleep"
The price is CA $154
CA $221 total
includes taxes & fees
Nov 18 - Nov 19
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Interior
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
10.0 out of 10, Exceptional, (22)
"This is the cutest little beach cottage, steps to the beach! The owner is very responsive and super hospitable. We will be staying again! "
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Waterfront property with private boat ramp and new dock!
Outdoor dining
Waterfront property with private boat ramp and new dock!
9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
Property grounds
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
10.0 out of 10, Exceptional, (16)
"We love this location and the hosts"
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
Comfortable cottage in gated community, 5 mins to OC and Assateague
Property grounds
Comfortable cottage in gated community, 5 mins to OC and Assateague
9.8 out of 10, Exceptional, (26)
"Very nice, clean and quiet location. Would definitely book again."
The price is CA $141
CA $447 total
includes taxes & fees
Nov 18 - Nov 19
Comfortable cottage in gated community, 5 mins to OC and Assateague
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Terrace/patio
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
8.4 out of 10, Very good, (48)
"The house was nice. Neighbor quiet. It was nice there is a small park across the street for the dog. Had everything I need in the house. It was nice I did not have to bring my own sheets and towels. They were supplied to us. The beach is a short drive up the street, maybe a minute or two and there was plenty of parking. I would stay here again if I go down to ocean city again."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Cozy Coastal Cottage Ocean Pines
Fridge, microwave, oven, stovetop
Cozy Coastal Cottage Ocean Pines
9.2 out of 10, Wonderful, (20)
"Property was just as shown and couldnt have asked for better communication."
Cozy Coastal Cottage Ocean Pines
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Exterior
Private Carriage House Retreat on a 33 Acre Historic Working Estate
10.0 out of 10, Exceptional, (11)
"Place was great !"
Private Carriage House Retreat on a 33 Acre Historic Working Estate
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
Private kitchen
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
9.2 out of 10, Wonderful, (10)
"Clean, modern, compact cottage and is PET FRIENDLY! Great screened in porch and small but nice area outside of cottage to enjoy personal fire pit.Pool, Laundry facility all close on site.Pet area was clean, grassy, well kept area for our large dog.Would def stay there again!Check in and communication with office was perfect-always quick With responses!❤️"
The price is CA $154
CA $221 total
includes taxes & fees
Nov 18 - Nov 19
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
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
Waterfront, cozy cottage with private pool on 27 acres
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres
9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Miscellaneous
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
A pair of bay view cottages with cable & free WiFi - walk 2 blocks to the beach
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
Chesapeake Romantic Waterfront Home with Private Pool
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
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.
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Other property types in Eastern Shore

Shore Point Cottages
Fridge, microwave, stovetop, dishwasher
Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, (199)
"We had an amazing time we even extended our stay . The management I believe her name was Erin was absolutely amazing , she was friendly and helpful . The property was so clean and so convienent. We will be back great place to stay ."
The price is CA $154
CA $216 total
includes taxes & fees
Nov 18 - Nov 19
Shore Point Cottages
Majestic Hotel & Apartments
Basic Apartment, 2 Bedrooms, Non Smoking | Private kitchen
Majestic Hotel & Apartments
3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments
Coconut Malorie Resort Ocean City a Ramada by Wyndham
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, (1236)
"A bit dated but still in good shape and decent value, big room. Water came in under the counter during heavy rain. Nevertheless, I'd stay again."
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.

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prices for cottages in Eastern Shore range between CA $141 and CA $154 per night. No matter your budget, you’ll find the perfect place to soak up nature’s beauty. These prices were 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?
There are multiple cottages in Eastern Shore with a total average guest review rating of 9.3, so you’ll easily discover a place that suits your style. Planning to stay in Ocean City? Frontier Town Campground is one property recommended by guests. This 2-star cottage includes handy amenities like a barbecue grill and a swimming pool. 103 79th Street 3 Bedroom Cottage By Redawning is another highly rated getaway where you can be in touch with nature. A nearby beach and a patio are a couple of the conveniences you can expect at this 3-star option in Ocean City.
How many cottages are there in Eastern Shore?
Eastern Shore has 26 cottages to choose from. Enter your dates and destination and plan your next escape today.
Why book your cottage in Eastern Shore with Expedia?
We think that traveling should be a piece of cake, so if you’re on the lookout for cottages in Eastern Shore at a nice price, Expedia delivers. Stick to the budget and opt for a low-cost option far from the rush of the city, or book a 5-star cottage to spoil your loved ones.
How can I find cheap cottages in Eastern Shore?
Expedia is here to help you easily track down cheap cottages in Eastern Shore. To lock in your dream stay in a few quick keystrokes, try out our convenient filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Eastern Shore near my cottage?
No matter your interests, there are countless things to keep you busy in Eastern Shore. If you’re heading to Ocean City, check out Ocean City Beach, Seacrets Distilling Company and Trimper’s Rides. Planning a getaway in Berlin? Globe Theater, Main Street Berlin and Calvin B. Taylor House Museum are among the top sights in this city.