Earleville Vacation Rentals from ￥12,063: Search Short-Term Rentals

Q: What's the top vacation rental that Earleville has to offer?

Chesapeake Bay House with Dock & Private Beach : This vacation home rental near Earleville is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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Vacation Rentals in Earleville

"Lovely cottage, well-equipped, immaculately clean. "

"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."

"Great place for a long weekend. Easy travel to surrounding areas to explore."

"Lovely location"

"Always a nice get away…."

￥41,187 total

includes taxes & fees

Aug 14 - Aug 15

"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. "

"This property was amazing! My family of six, really enjoyed the pool, large yard, for one including a balcony, toys for the kids, and many more! Will definitely be staying again in the future"

￥198,574 total

includes taxes & fees

Aug 14 - Aug 15

"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."

"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"

"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "

"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."

￥24,059 total

includes taxes & fees

Aug 14 - Aug 15

Beach nearby, sun loungers, beach towels

"This is a jewel as it is private, peaceful with lovely setting."

"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "

"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "

"a great place to unwind. "

"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...

￥47,921 total

includes taxes & fees

Aug 25 - Aug 26

"Exactly as advertised and Brad was very helpful/responsive!"

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Top Earleville Hotel Reviews

Ramada by Wyndham Newark/Wilmington

10/10 Excellent

"Great location and accommodating staff. Room was clean and neat. Could have had better TV reception though. That’s the only drawback."

Baymont by Wyndham Newark at University of Delaware

10/10 Excellent

"The trip was for a vist with friends. It was conveniently located to the various venues. Manager at the time of checkin was friendly and accommodating. The room was clean. I will say I have not seen the type of shower but it was all clean. There is no tub. Vanity is just outside the bathroom in the room. "

Find out more about Earleville

Search for holiday rentals in Earleville on Expedia! You can easily find your home rentals, villas, holiday apartments in Earleville using one of the methods below:

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Frequently asked questions

Can I find vacation rentals in Earleville?

Yes, you can find vacation rentals near popular sights in Earleville, or you can choose a more remote option if you want a relaxing place to stay. Earleville is known for its museums.

What's the top vacation rental that Earleville has to offer?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Earleville is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Earleville?

Expedia has 6 vacation 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 Earleville Wildlife Management Area are other places to visit while you're in town.

What are vacation rentals like in Earleville?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Earleville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.

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Earleville Vacation Rentals

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Vacation Rentals in Earleville

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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

Chesapeake Bay House with Dock & Private Beach

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

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

Historic Chesapeake City Stay

Historic Downtown Garden Oasis with Private Patio

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Stay & Play at Our Beautiful Retreat

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

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

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

Summer Rustic Camping with AC and King Bed

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

* NEWLY RENOVATED** Escape to a Beautiful Getaway on the Chesapeake Bay

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

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Waterfront house with amazing views. Top of the Chesapeake

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

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!