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

Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun
Shore Point Cottages
Private kitchen

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (204)
"I love how quiet the place is. It gives you a remote feeling. A very nice getaway!"
Shore Point Cottages
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier
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, (175)
"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
Dog-Friendly Westover Cottage w/ River Access!
Fridge, microwave, stovetop, dishwasher

Dog-Friendly Westover Cottage w/ River Access!

9.8 out of 10, Exceptional, (7)
"Overall very good. Bath/shower needs upgrade Gas fireplace hard to start. May need maintenance Very pet friendly. Dog bowls, bed, and toys on site Owner allowed early arrival and was responsive quickly to any questions that we had "
Dog-Friendly Westover Cottage w/ River Access!
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, (117)
"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
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, (136)
"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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
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
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
View from property

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (38)
"This weekend, we had the pleasure of staying at Mark and Karen's place, and it was truly immaculate and thoughtfully designed. They’ve considered every detail, providing everything you could possibly need for a fantastic stay.One of the main reasons we chose this house was to have a gathering with our brother, who uses a wheelchair. This house checks all the boxes for accessibility. The doors throughout the home are wide enough to easily accommodate a larger wheelchair, including the doorways to...
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Outdoor dining

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

4.6 out of 10, (7)
"My family and I stayed at the Parrot Bay Condo for the first time this year. We had fun! My children enjoyed the bunk bed, and the cottage where we used to stay every summer did not have a pool, so having the 3-5 foot pool was another feature that enhanced our vacation this year. I wished I had a fly swatter because flies do get in the house, but we would stay here again if it’s available again next year. Recommended!"
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
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 HK$778
HK$2,393 total
includes taxes & fees
4 May - 5 May
Comfortable cottage in gated community, 5 mins to OC and Assateague
Charming 2-bedroom cottage in the heart of West Ocean City
Microwave, dishwasher

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

10.0 out of 10, Exceptional, (1)
The price is HK$1,066
HK$2,341 total
includes taxes & fees
9 Apr - 10 Apr
Charming 2-bedroom cottage in the heart of West Ocean City
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

10.0 out of 10, Exceptional, (91)
"It was a lovely property that had everything our family needed. It was convenient to the shore and the local attractions."
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.
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, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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)
"This was one of the most beautiful spots I've seen. Kayaking was wonderful! Couch was very uncomfortable. And many maybe put off to find they must put everything in a box to keep away from rodents. And I just took my garbage home as we didn't have time to dump at an off site location on vacation. I would still book again as it was the most peaceful, charming and secluded place to truly relax!"
Private waterfront cottage with pool on Church Creek
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"
Long Beach Cottage, (romantic couple’s getaway)
Grasonville Home w/ Private Pool on the Water
Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Charming Salisbury Getaway w/ Grill & Fire Pit!
Interior

Charming Salisbury Getaway w/ Grill & Fire Pit!

3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!
Cottage downtown on a quiet street
Marina

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
Charming 1-bedroom cottage in downtown Saint Michaels
Interior

Charming 1-bedroom cottage in downtown Saint Michaels

Charming 1-bedroom cottage in downtown Saint Michaels
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

Shore Point Cottages
Private kitchen

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (204)
"I love how quiet the place is. It gives you a remote feeling. A very nice getaway!"
Shore Point Cottages
Majestic Hotel & Apartments
Private kitchen

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments
Saint Tropez
Exterior

Saint Tropez

3.0 star property
9.0 out of 10, Wonderful, (90)
"Relaxing and beautiful views with easy access to the beach. The room has all needed amenities: oven, coffee maker, microwave, washer and dryer. "
Saint Tropez
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?
Prepare to pay between and per night for cottages in Eastern Shore. No matter your budget, a fantastic stay is just clicks away on Expedia. 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?
Slide straight into holiday mode and take life at a gentler pace in one of Eastern Shore’s multiple cottages. With a total average guest review rating of 9.2, there’s something here for everyone, no matter your style and budget. Many visitors to Ocean City prefer staying at Frontier Town Campground, a 2-star cottage retreat with a barbecue grill and a swimming pool. Another highly rated option here is 103 79th Street 3 Bedroom Cottage By Redawning. This 3-star property offers clothes washing facilities and WiFi.
How many cottages are there in Eastern Shore?
Take your pick of 27 cottages in Eastern Shore. Whether you’re travelling with the whole family, as a couple or with a group of workmates, Expedia will help you find the perfect space.
Are there any family-friendly cottages in Eastern Shore?
There are indeed. Whether it’s in one of Eastern Shore’s renowned cities or way out in nature, the unique charm of a cottage is perfect for family fun. If Ocean City is your preferred destination, check out Frontier Town Campground. This 2-star option features a playground and WiFi. Another top choice is 103 79th Street 3 Bedroom Cottage By Redawning. Also in Ocean City, this family-friendly cottage has a 3-star rating and includes clothes washing facilities and WiFi. Ocean City has many family-friendly attractions when it’s time to get out and explore. Inlet Park and Golf Down Under has something for all ages.
Why book your cottage in Eastern Shore with Expedia?
Booking a cottage in Eastern Shore is as easy as deciding on your travel dates and picking your ideal place for a getaway in the outdoors. From luxurious retreats to budget-friendly stays and cottages that feature amenities like a kitchenette, Expedia has something for all traveller tastes. As for unbeatable deals? We’ve have them as well!
How can I find cheap cottages in Eastern Shore?
The quickest way to score cheap cottages in Eastern Shore is with Expedia’s filter tool. Narrow your search by budget, star rating and amenities to snag awesome rates in a couple of clicks.
What is there to do in Eastern Shore near my cottage?
The best accessory to take on your Eastern Shore holiday is a good itinerary! Jolly Roger at the Pier, Inlet Park and Ember’s Island Miniature Golf are some of the most popular sights if you’re heading to Ocean City. Salisbury also has plenty of superb attractions, such as Poplar Hill Mansion. Want to explore more? Visit Pemberton Historical Park and Ward Museum of Wildfowl Art too.