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Check prices for these dates

Next weekend
25 Jul - 27 Jul
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1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Eastern Maryland

Shore Point Cottages
Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher

Shore Point Cottages

3.0 star property
9.2 out of 10, Wonderful, (260)
"Excellent stay i will come back "
Shore Point Cottages
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (5)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
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, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (250)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

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

10.0 out of 10, Exceptional, (4)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Fridge, microwave, oven, stovetop

Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower

9.0 out of 10, Wonderful, (2)
"We enjoyed our stay at Parrot Bay. The decor was perfect for the beach and it had all of the amenities we needed. We liked the coffee machine, televisions in the bedrooms and living room, and cozy furniture. It was a short walk to the boardwalk, and the pool was a nice bonus!"
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Charming 2-bedroom cottage in the heart of West Ocean City
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage in the heart of West Ocean City

9.4 out of 10, Exceptional, (3)
"Very nice cottage and some good restaurants near by"
Charming 2-bedroom cottage in the heart of West Ocean City
Comfortable cottage in gated community, 5 mins to OC and Assateague
Outdoor pool

Comfortable cottage in gated community, 5 mins to OC and Assateague

9.8 out of 10, Exceptional, (32)
"We enjoyed staying at this property. We have stayed at Assateague point several times in the past and will be back."
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, (49)
"This house is in a great location. Quiet, friendly neighbors, and a large park right across the street for the dogs. We would definitely stay there again."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
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)
"Close to beach and shopping"
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Private waterfront cottage with pool on Church Creek
Fridge, microwave, oven, stovetop

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"Very clean, comfortable, and cozy property with gorgeous view of the water. Would definitely stay here again. Just wish we spent more time on the property this stay, but obligations in Fishing Creek kept us away most of the time. Thank you for sharing your lovely cottage!!"
Private waterfront cottage with pool on Church Creek
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette
Fridge, microwave, oven, dishwasher

Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette

10.0 out of 10, Exceptional, (1)
"Location and having a place to yourself was perfect for a quiet getaway weekend."
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette
New to VRBO! Cozy cottage close to everything!
Fridge, microwave, oven, stovetop

New to VRBO! Cozy cottage close to everything!

10.0 out of 10, Exceptional, (4)
"This place was great. Close to everything you could want, and the host was very helpful. He gave suggestions on which beaches to go to and where the best food is. My wife and I had a hell of a time. We will definitely be back"
New to VRBO! Cozy cottage close to everything!
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, (121)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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, (118)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Boho chic modern 1-bedroom cottage with AC, WiFi in the heart of West Ocean City
Exterior detail

Boho chic modern 1-bedroom cottage with AC, WiFi in the heart of West Ocean City

10.0 out of 10, Exceptional, (1)
"This place was perfect! Accommodations were fantastic. Communication with owner (Karen) was fast and efficient. Could not have asked for a better place to stay while in Ocean City for a work project. Thank you! Hope to come back on next project."
Boho chic modern 1-bedroom cottage with AC, WiFi in the heart of West Ocean City
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, (140)
"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
Charming Salisbury Getaway w/ Grill & Fire Pit!
House (3 Bedrooms) | Interior

Charming Salisbury Getaway w/ Grill & Fire Pit!

3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!
Updated Home - Walk to Salisbury University!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Updated Home - Walk to Salisbury University!

3.0 star property
Updated Home - Walk to Salisbury University!
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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Top Eastern Maryland Hotel Reviews

Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Clean hotel , great pool bar and restaurant. I would definitely go back. I just wish the pool and bar didn’t close at 8 pm. Especially in summertime. That would be my only complaint, otherwise is was great and the location on the boardwalk was perfect!"
Jennifer 4-night trip
Posted 19 hours ago
Crystal Beach Hotel

Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between and per night. These retreats offer a chance to reconnect with nature — at a price you can afford. 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.
How many cottages are there in Eastern Maryland?
You can pick from 27 cottages in Eastern Maryland. Whether you're traveling with your family, as a duo or with a group of friends, Expedia can help you secure your ideal digs.
Why book your cottage in Eastern Maryland with Expedia?
We think that traveling should be easy, so if you're after cottages in Eastern Maryland at a great price, Expedia is here to help. Keep the budget under control and choose an economical option far from the rush of the city, or book a luxury cottage to spoil the ones you love most.