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Holiday Rentals in Earleville

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Holiday Rentals in Earleville

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (45)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (169)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (34)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is €245
includes taxes & fees
24 Aug - 25 Aug
Historic Chesapeake City Stay

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Very beautiful with private waterfront. Roomy and clean. Like another world away ."
The price is €570
includes taxes & fees
1 Sept - 2 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (98)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is €132
includes taxes & fees
21 Aug - 22 Aug
First Floor Studio Apartment in Historic Chestertown

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
The price is €276
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom cabin close to Fair Hill on horse farm

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (60)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

Sailor's Sunrise Cottage - Chesapeake Bay

9.6 out of 10, Exceptional, (51)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay

Stay & Play at Our Beautiful Retreat

10.0 out of 10, Exceptional, (3)
"This property has everything you need for a friends weekend. Pickelball, pool, basketball, even golf hitting net were all used by our group and we enjoyed the TV room and large outdoor space. Takes a little navigating to get there, but the directions were well done and communication with the owner was great. They were very responsive to all of our questions. Would highly recommend this place for groups."
Stay & Play at Our Beautiful Retreat

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

10.0 out of 10, Exceptional, (19)
"Very nice cottage, as advertised"
The price is €182
includes taxes & fees
1 Sept - 2 Sept
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (30)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"The property is everything it claims to be & more. Awesome location on the bay. Great accommodations. So peaceful. We had a wonderful time. Would highly recommend! "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Summer Rustic Camping with AC and King Bed

9.6 out of 10, Exceptional, (4)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
The price is €155
includes taxes & fees
25 Aug - 26 Aug
Summer Rustic Camping with AC and King Bed
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 Earleville Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Earleville?

Yes, there are holiday rentals close to the most popular sights in Earleville, or you can select a more secluded option if you're looking for a relaxing stay. Earleville is known for its museums.

What are some of the best holiday rentals that Earleville has to offer?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Earleville is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Earleville?

Expedia has 6 holiday rentals for your stay in Earleville.

What can I see and do in Earleville?

Earleville Wildlife Management Area and Cecilton Park are a couple of lovely local spots to get outside and enjoy nature. Hack's Point Marina and Sassafras Harbor Marina are other places to visit while you're in town.

What are holiday rentals like in Earleville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Earleville. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.