Search Eastern Shore Cottages

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

Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, 62 reviews
"Very comfortable, well appointed units. Loved the screened in front porch and side patios. Tasteful decor with practical touches, such as separate air conditioning units, 3 tv’s and plenty of wall hooks. Thank you for being pet friendly! "
Shore Point Cottages
cottage, community pool, playground, boating, crabbing kayaking and fishing!!!
10.0 out of 10, Exceptional, 2 reviews
"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!!!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, 152 reviews
"Cute, quaint, conveniently located home. Lovely stay!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, 85 reviews
"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
Waterfront property with private boat ramp and new dock!
Waterfront property with private boat ramp and new dock!
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
10.0 out of 10, Exceptional, 4 reviews
"We enjoyed our weekend stay. Everything was new and clean. It was a quiet stay away from the hustle and bustle of OCMD. Like other guests, we tried to contact the owner with questions during our stay and got no response. There was also no check out instructions, so we were not sure how they wanted trash and bed linens handled. Everything was great except for communication."
Deluxe Cottage - 2 Bedroom Cabin 5 - Deluxe Cottage with two bedrooms.
Comfortable cottage in gated community, 5 mins to OC and Assateague
9.6 out of 10, Exceptional, 13 reviews
"VERY NICE NEIGHBORHOOD. QUIET AND PRESTINE. COTTAGE WAS COMFORTABLE, HOMEY, CLEAN AND VERY WELL APPOINTED. WOULD RECOMMEND IT TO FREINDS AND FAMILY MEMBERS. OWNERS WERE VERY ACCOMMADATING. SPENT AT LEAST AN HOUR WITH THEM TO WALK US TROUGH SIGNING INTO THE TV. SUCH PATIENCE!! WE ARE NOT VERY TECH SAVVY. THEY WERE VERY PLEASEANT. WE TRULY APPRECIATED THEIR WILLINGNESS TO BE OF HELP TO US. NEIGHBORS WE PLEASANT AND FRIENDLY."
The price is $225
$473 total
includes taxes & fees
Jun 16 - Jun 17
Comfortable cottage in gated community, 5 mins to OC and Assateague
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
8.8 out of 10, Excellent, 5 reviews
"I'm originally from Salisbury and we grew up traveling to OC most weekends, so finding the right place to stay was so important. This is a newer property, well kept and peaceful. We will be booking again in the future for our church retreats and family getaways."
Deluxe Cottage - 2 Bedroom Cabin 1 - Deluxe Cottage with two bedrooms.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, 127 reviews
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
9.8 out of 10, Exceptional, 14 reviews
"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
Your Own Stonegate Cottage— North OC—4 blocks to the Beach
10.0 out of 10, Exceptional, 13 reviews
"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
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
8.4 out of 10, Very Good, 41 reviews
"clean, great location, well equipped cottage, nice park across street for dogs."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Cozy Coastal Cottage Ocean Pines
9.0 out of 10, Wonderful, 15 reviews
"Good neighborhood. Communication with host was great! Nice OC home!! Would stay again."
Cozy Coastal Cottage Ocean Pines
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, 90 reviews
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Private Carriage House Retreat on a 33 Acre Historic Working Estate
10.0 out of 10, Exceptional, 8 reviews
"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
Holiday Cottage-Oceanside 77th St, W/D, AC, Free WIFI
8.4 out of 10, Very Good, 11 reviews
"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
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
9.8 out of 10, Exceptional, 16 reviews
"Family of 5 & our dog stayed for holiday weekend…..area was so nice and peaceful with beautiful views of the bay. House was well maintained. Jessica was easy to communicate with. We will definitely be back! We had an amazing visit!"
-Sunset River Shack-Amazing water views of the upper Chesapeake bay
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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

Majestic Hotel & Apartments
3.0 star property
6.6 out of 10, 76 reviews
"Plumbing needs work but fantastic stay! "
The price is $102
$124 total
includes taxes & fees
Jul 2 - Jul 3
Majestic Hotel & Apartments
Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, 62 reviews
"Very comfortable, well appointed units. Loved the screened in front porch and side patios. Tasteful decor with practical touches, such as separate air conditioning units, 3 tv’s and plenty of wall hooks. Thank you for being pet friendly! "
Shore Point Cottages
Near it all OC beaches,Assateague island.Family-friendly white horse park
10.0 out of 10, Exceptional, 12 reviews
"This place was perfect for us. We were coming for a quick getaway and this place was extremely clean, no weird smells, and looks like the pictures. Two things I want to mention that could help with booking is the campground does rent out bikes and I think kayaks which would have been helpful to know ahead of time. Also we couldn’t find towels which was a first for me in a bnb. Not a big deal for us because we wanted new ones for home anyway. Thanks for a great weekend and we will definitely be...
Near it all OC beaches,Assateague island.Family-friendly white horse park
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
762
Accommodation
24 Cottages
Lowest Price
$225
Highest Price
$225

Frequently asked questions

How much do cottages in Eastern Shore cost?
Cottages in Eastern Shore range between $225 and $225 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 9.5, 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 24 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.

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