A marina with numerous sailboats docked at wooden piers.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Eastern Maryland cottages

Exterior

1. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 reviews)
"We were there for our granddaughter's wrestling tournament in Salisbury. House was excellent, quiet and clean. Beautiful home. Thank you."
United States
Christopher M.
The price is ￥22,364
￥40,769 total
includes taxes & fees
Sep 20 - Sep 21
Deal Island Bay Cottage
Exterior

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

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (54 reviews)
"Convenient amenities at Assateague Point, easy access to Assateague Island and OCMD. Everything in the unit was clean, in proper working order, and we had everything we needed for our family with young children. Would definitely stay here again."
United States
Alexandra
The price is ￥20,943
￥56,294 total
includes taxes & fees
Sep 22 - Sep 23
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

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

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (53 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is ￥27,427
￥32,883 total
includes taxes & fees
Sep 20 - Sep 21
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Property grounds

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

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (17 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥20,816
￥33,329 total
includes taxes & fees
Sep 24 - Sep 25
Quarry Landing - Center of Town & River View - 3 Bedroom
House (6 Bedrooms) | Interior

5. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
The price is ￥91,736
￥188,392 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines
Palm Cottage | 1 bedroom, premium bedding, laptop workspace, soundproofing

6. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (640 reviews)
"This was the perfect relaxing get away! Clean and quiet! Already booked for next spring 2027!"
United States
LaTonya
The price is ￥31,520
￥35,396 total
includes taxes & fees
Oct 18 - Oct 19
Key West Cottages
Exterior

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

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Georgetown
9.8 out of 10, Exceptional, (62 reviews)
"We stayed at this property for 6 nights, everything was exactly like the pictures and very clean. We were just far enough to many shopping areas and grocery stores. It was very quiet and peaceful. Ed and Cindy are amazing hosts, we will be returning next year!"
United States
Haileigh
The price is ￥15,628
￥33,835 total
includes taxes & fees
Oct 11 - Oct 12
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
House (3 Bedrooms) | Interior

8. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is ￥24,536
￥62,979 total
includes taxes & fees
Sep 26 - Sep 27
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Exterior

9. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (61 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is ￥22,082
￥46,931 total
includes taxes & fees
Oct 5 - Oct 6
Soul Oasis - home on the Chesapeake Bay
Exterior

10. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
The price is ￥25,580
￥53,026 total
includes taxes & fees
Oct 1 - Oct 2
Pet-friendly creekside cottage w/ backyard
Exterior

11. Oasis at Muchy Branch

Oasis at Muchy Branch
Midway
9.8 out of 10, Exceptional, (27 reviews)
"Very pet friendly for my two small dogs 9lbs and 15lbs.So satisfied I think we will return the end of September for a few days."
United States
Bill G.
The price is ￥14,799
￥47,421 total
includes taxes & fees
Sep 22 - Sep 23
Oasis at Muchy Branch
Exterior

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

Charming 1-bedroom cottage with loft in Rehoboth Beach
Truitts Park
9.8 out of 10, Exceptional, (25 reviews)
"loved our stay!"
United States
Clair H.
The price is ￥23,890
￥55,060 total
includes taxes & fees
Oct 13 - Oct 14
Charming 1-bedroom cottage with loft in Rehoboth Beach
Living area

13. Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA

Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
Up the Neck
The price is ￥40,089
￥49,389 total
includes taxes & fees
Oct 1 - Oct 2
Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA
Exterior

14. Heart of Amish Country - Paradise Cottage

Heart of Amish Country - Paradise Cottage
Paradise
10.0 out of 10, Exceptional, (63 reviews)
"Great location, super clean and the host was very thoughtful with all the sweet treats provided for us. The coffee bar was well stocked and the kitchen had everything needed for our weekend stay."
United States
Tammy W.
The price is ￥20,632
￥40,827 total
includes taxes & fees
Sep 21 - Sep 22
Heart of Amish Country - Paradise Cottage
Exterior

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

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is ￥52,679
￥76,776 total
includes taxes & fees
Oct 5 - Oct 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Exterior

16. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (18 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is ￥34,694
￥67,649 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior

17. Thunder Hill Retreat - Spacious/Deck/Hot tub

Thunder Hill Retreat - Spacious/Deck/Hot tub
Lincoln University
10.0 out of 10, Exceptional, (24 reviews)
"Great place to get away! Peaceful, serene with amenities to boast!"
United States
Arthur B.
The price is ￥33,883
￥75,666 total
includes taxes & fees
Sep 21 - Sep 22
Thunder Hill Retreat - Spacious/Deck/Hot tub
House (3 Bedrooms) | Interior

18. 2 Mi to Bethany Beach! Family Getaway w/ Deck

2 Mi to Bethany Beach! Family Getaway w/ Deck
3.0 star property
Savannah's Landing
10.0 out of 10, Exceptional, (1 review)
"Everything was fine, looking forward to come back!"
United States
Marlon
The price is ￥24,223
￥66,206 total
includes taxes & fees
Oct 5 - Oct 6
2 Mi to Bethany Beach! Family Getaway w/ Deck
Property grounds

19. Cozy Spring House in Gorgeous Chadds Ford!

Cozy Spring House in Gorgeous Chadds Ford!
Chadds Ford
9.8 out of 10, Exceptional, (87 reviews)
"We enjoyed Cozy Cottage and would come back again!"
United States
ken s.
The price is ￥31,256
￥54,535 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Spring House in Gorgeous Chadds Ford!
Exterior

20. Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!
Milton
9.8 out of 10, Exceptional, (38 reviews)
"Love how pet friendly it was a so close to the beach!"
United States
Lauren B.
The price is ￥33,616
￥75,136 total
includes taxes & fees
Oct 14 - Oct 15
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!
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

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

10/10 Excellent
"The first night we couldn’t sleep with a loud rattling sound from the air conditioning I taped the sound from the horrible evening and morning The staff was so kind and immediately suggested a room change It was greatly appreciated for the next 2 nights"
Elizabeth 3-night trip
Posted less than an hour ago
Hyatt Place Ocean City / Oceanfront

Find out more about Eastern Maryland

Eastern Maryland Cottages information

Number of reviews
732
Accommodation
18 Cottages
Lowest Price
￥32,883
Highest Price
￥188,392

Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between ￥32,883 and ￥188,392 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 18 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.
How can I find cheap cottages in Eastern Maryland?
The easiest way to score cheap cottages in Eastern Maryland is with Expedia's useful filter tool. Fine-tune your search results by amenities, star rating and budget to access unbeatable rates in a few clicks.
What is there to do in Eastern Maryland near my cottage?
There are plenty of exciting attractions to explore when traveling through Eastern Maryland. If you're planning a couple of days in Seaford, Williams Pond Park is a must-see.

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