Search Cottages in Eastern Shore

  • 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 32 Cottages in Eastern Shore with updated reviews, rates, and availability.

Shore Point Cottages
Exterior

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (201)
"Awesome place to visit "
Shore Point Cottages
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

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 SAR 376
SAR 1,188 total
includes taxes & fees
20 Jan - 21 Jan
Comfortable cottage in gated community, 5 mins to OC and Assateague
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Outdoor dining

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
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (113)
"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!
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
Exterior detail

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
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (116)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower

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
Outdoor dining

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
Front of Carpenter St. Cottage

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (171)
"The Carpenter Street Cottage is a great place to stay. Very clean and comfortable and has all of the necessary amenities. The location is perfect for walking throughout the town. I will definitely stay there again! "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
Exterior

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
Private Pool

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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (135)
"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
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
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (14)
"The house is great, so clean and well-equipped and has everything you need for a comfortable stay. Kim delivered delicious crabs right to the dinner table! We enjoyed riding the bikes around the island. Smith Island Bakery is only a few doors down!"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Chesapeake Romantic Waterfront Home with Private Pool
Pool closed in winter and virtually staged because it was closed during pic.

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
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront property with private boat ramp and new dock!
Exterior

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!
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa
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.
Don't see what you're looking for?
See all available properties in Eastern Shore
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Eastern Shore

Majestic Hotel & Apartments
Exterior

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments
Shore Point Cottages
Exterior

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (201)
"Awesome place to visit "
Shore Point Cottages
Coconut Malorie Resort Ocean City a Ramada by Wyndham
Room

Coconut Malorie Resort Ocean City a Ramada by Wyndham

3.0 star property
7.4 out of 10, Good, (1236)
"Nice to have a kitchen and separate bedroom "
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 SAR 376 and SAR 376 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 9.4, so you’re sure to find a place that suits your tastes. Planning to stay in Ocean City? Frontier Town Campground is one property recommended by guests. This 2-star cottage includes 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 unwind close to nature. Clothes washing facilities and a patio are just two of the conveniences waiting for you at this 3-star option in Ocean City.
How many cottages are there in Eastern Shore?
Eastern Shore has 32 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.