Eastern Shore Cottages from CA $282

A marina with numerous boats docked at wooden piers under a clear sky.

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Our top choices for Eastern Shore cottages

A single-story mobile home with a front porch and steps leading to the entrance.

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

Assateague Pointe

Joe

CA $512 total

includes taxes & fees

Oct 19 - Oct 20

A single-story house with a front porch, a staircase leading to the entrance, and a small deck.

2. Deal Island Bay Cottage

Deal Island

"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"

Harold B.

CA $368 total

includes taxes & fees

Oct 19 - Oct 20

A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

3. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Port Deposit

Nimia N.

CA $298 total

includes taxes & fees

Oct 21 - Oct 22

A wooden deck with a white railing overlooking a calm body of water and a distant bridge.

4. Game Room! Waterfront Group Haven in Ocean Pines

Ocean Pines

CA $1,130 total

includes taxes & fees

Oct 18 - Oct 19

A residential area with houses, a parking lot, and a body of water in the background.

5. Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit

jerel p.

CA $328 total

includes taxes & fees

Nov 9 - Nov 10

A row of mobile homes with a one-way sign, a covered porch, and a street sign indicating 'Shore Point Lane'.

6. Shore Point Cottages

Berlin

Kelly

A waterfront house with a balcony, dock, and a view of the water.

7. Key West Cottages

Downtown Chincoteague

Melissa

CA $282 total

includes taxes & fees

Nov 17 - Nov 18

A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

8. EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Georgetown

Kay Lorelle R.

CA $303 total

includes taxes & fees

Oct 19 - Oct 20

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

9. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

ed r.

CA $381 total

includes taxes & fees

Oct 18 - Oct 19

A residential property with a swimming pool, a covered patio, and a two-story house with a balcony.

10. Luxury Home 3 Mi to Bethany Beach Boardwalk!

Ocean View

CA $638 total

includes taxes & fees

Oct 31 - Nov 1

A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

11. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

West Annapolis

Jill R.

CA $638 total

includes taxes & fees

Nov 5 - Nov 6

A single-story house with a covered porch, a number '374' on the side, and a covered grill area.

12. Charming 1-bedroom cottage with loft in Rehoboth Beach

Truitts Park

Clair H.

CA $489 total

includes taxes & fees

Oct 18 - Oct 19

A single-story house with a porch, a small front yard, and an American flag.

13. Plum Point Cottage #1

Calvert County

CA $722 total

includes taxes & fees

Oct 24 - Oct 25

14. Pet-friendly creekside cottage w/ backyard

Up the Neck

Christine

CA $521 total

includes taxes & fees

Oct 18 - Oct 19

A covered porch with wooden flooring, two wicker chairs with cushions, a small table, and a potted plant.

15. Plum Point Cottage #14

Huntingtown

Yonnick H.

CA $774 total

includes taxes & fees

Oct 18 - Oct 19

An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

16. Plum Point Cottage #15

Maryland

CA $818 total

includes taxes & fees

Oct 18 - Oct 19

A covered patio with a table and chairs, large windows, and an American flag.

17. Plum Point Cottage #17

Huntingtown

CA $636 total

includes taxes & fees

Oct 18 - Oct 19

A sunlit patio with wicker furniture, a potted plant, and a decorative rug.

18. Ocean Block Dewey Beach and Pet Friendly!

Rehoboth by the Sea

Kelly B.

CA $759 total

includes taxes & fees

Nov 1 - Nov 2

A wooden deck with wicker furniture, a round table, and a fire pit.

19. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena

Buu T.

CA $940 total

includes taxes & fees

Oct 21 - Oct 22

A covered patio with a table and chairs, a white fence, and a view of the greenery.

20. Getaway on 1/2 Acre w/ Deck in Georgetown

Georgetown

ANA

CA $472 total

includes taxes & fees

Nov 9 - Nov 10

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Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

8/10 Good

"Great oceanfront location suites were clean & spacious whirlpool tub was a plus will definitely be staying there again"

The Americana Hotel

8/10 Good

"The staff here are wonderful—everyone was so friendly and helpful! Unfortunately, the housekeeping fell short. The room wasn't cleaned until we requested it, the bed wasn't made on our second day, and the bathrooms weren't cleaned properly. Housekeeping only emptied the trash and brought fresh towels. With better room cleaning, this would have been a much better stay."

St Michaels Inn

8/10 Good

"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."

Find out more about Eastern Shore

Eastern Shore Cottages information

Number of reviews	1,133
Accommodation	27 Cottages
Lowest Price	CA $282
Highest Price	CA $1,130

Frequently asked questions

How much do cottages in Eastern Shore cost?

Prepare to pay between CA $282 and CA $1,130 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?

Eastern Shore offers multiple cottages with a total average guest review rating of 9.7. Planning a trip to Ocean City? Travellers prefer Frontier Town Campground, a 2-star property with a swimming pool and a barbecue grill. Another top pick where you can escape the hustle and bustle is 103 79th Street 3 Bedroom Cottage By Redawning. It has a 3-star rating and amenities such as a nearby beach and a patio.

How many cottages are there in Eastern Shore?

Take your pick of 27 cottages in Eastern Shore. Whether you're traveling 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 sure are. Whether it's in one of Eastern Shore's bustling cities or way out in the wilderness, the unique charm of a cottage is ideal for family fun. If Ocean City is your destination, book a stay at Frontier Town Campground. This 2-star option features a playground and clothes washing facilities. Another great 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. After you've unpacked your luggage, it's time to discover the best of Ocean City. Look forward to memorable moments together at family-friendly attractions like 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 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 traveler 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 vacation 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.

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Search Eastern Shore Cottage Rentals from CA $282

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Eastern Shore cottages

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

2. Deal Island Bay Cottage

3. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

4. Game Room! Waterfront Group Haven in Ocean Pines

5. Quarry Landing - Center of Town & River View - 3 Bedroom

6. Shore Point Cottages

7. Key West Cottages

8. EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

9. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

10. Luxury Home 3 Mi to Bethany Beach Boardwalk!

11. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

12. Charming 1-bedroom cottage with loft in Rehoboth Beach

13. Plum Point Cottage #1

14. Pet-friendly creekside cottage w/ backyard

15. Plum Point Cottage #14

16. Plum Point Cottage #15

17. Plum Point Cottage #17

18. Ocean Block Dewey Beach and Pet Friendly!

19. Chesapeake Cottages- 2 Quaint Waterfront Retreats

20. Getaway on 1/2 Acre w/ Deck in Georgetown

Find vacation rentals that suit your style

Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

Find out more about Eastern Shore

Eastern Shore Cottages information

Frequently asked questions

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