Compare Eastern Maryland Cottage Rentals

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Featured Cottages in Eastern Maryland

Shore Point Cottages

Shore Point Cottages

3 out of 5
9543 Stephen Decatur Hwy Berlin MD
$124 nightly
The price is $138 total per night
$138 total
Dec 17 - Dec 18
Total with taxes and fees
At Shore Point Cottages, guests have access to a seasonal outdoor pool, laundry facilities, and a vending machine. A stay here includes free parking.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Comfortable cottage in gated community, 5 mins to OC and Assateague

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

Berlin MD
$275 nightly
The price is $305 total per night
$305 total
Dec 17 - Dec 18
Total with taxes and fees
Guests staying at this cottage enjoy an outdoor pool, an arcade/game room, and laundry facilities. This family-friendly cottage also has a garden.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD
At this cottage, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

Cambridge MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette

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

Ocean City MD
Guests of this cottage enjoy access to a water park, laundry facilities, and a garden.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

Elkton MD
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton MD
This cottage features an outdoor pool and laundry facilities.
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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.

Hotel Options in Eastern Maryland

    Grand Hotel Ocean City Oceanfront

    Grand Hotel Ocean City Oceanfront

    2100 N Baltimore Ave Ocean City MD
    $68 nightly
    The price is $76 total per night from Jan 7 to Jan 8
    $76 total
    Jan 7 - Jan 8, 2026
    Total with taxes and fees
    9/10 Wonderful! (3,347 reviews)
    Hyatt Place Ocean City / Oceanfront

    Hyatt Place Ocean City / Oceanfront

    1 16th Street Ocean City MD
    $80 nightly
    The price is $89 total per night from Dec 21 to Dec 22
    $89 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9/10 Wonderful! (1,589 reviews)
    Hilton Garden Inn Ocean City Oceanfront

    Hilton Garden Inn Ocean City Oceanfront

    2800 Baltimore Ave Ocean City MD
    $71 nightly
    The price is $79 total per night from Dec 21 to Dec 22
    $79 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9/10 Wonderful! (1,094 reviews)

Cottages

Book a cottage in Eastern Maryland
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Eastern Maryland. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Eastern Maryland better.

Cottage apartments in Eastern Maryland range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Eastern Maryland
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Eastern Maryland and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Eastern Maryland cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Eastern Maryland. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Eastern Maryland Cottages essential information

Accommodation
53 Cottages
Lowest Price
$76
Highest Price
$305
Popular accommodation
Shore Point Cottages, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Comfortable cottage in gated community, 5 mins to OC and Assateague, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Family and Pet-Friendly, Waterfront with Pier, Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly), Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette, Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC, Chesapeake City Pool Retreat – Waterfront Stay in the Woods

More to Explore