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Compare 143 Vacation Homes in Earleville with updated reviews, rates, and availability.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"The house was perfect. While the weather didn't really cooperate still had time to sit on the dock and the porch watching the eagles, osprey, geese, ducks, birds and fishermen. Location near Charlestiwn and NorthEast us freat fir restaurants and shopping "
Captivating Chesapeake experience

Beautiful Colonial Style Home in Nottingham PA

9.6 out of 10, Exceptional, (10)
"We had a great stay at this house! It was clean, comfortable and "
Beautiful Colonial Style Home in Nottingham PA

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

8.0 out of 10, Very Good, (1)
"Nice and quiet place to stay"
The price is AED 496
AED 1,032 total
includes taxes & fees
27 Apr - 28 Apr
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (37)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (136)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,319
AED 2,398 total
includes taxes & fees
13 May - 14 May
5-bedroom vacation home 5 minutes from historic Charlestown

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (14)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
The price is AED 624
AED 1,297 total
includes taxes & fees
28 Apr - 29 Apr
Tip Of The Town Fresh and New 3 Bedroom Nest

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

9.8 out of 10, Exceptional, (13)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

8.2 out of 10, Very Good, (12)
"Thanks Sean "
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is AED 2,071
AED 4,064 total
includes taxes & fees
27 Apr - 28 Apr
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (10)
"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Cozy 2-bedroom townhome in charming Elkton

8.0 out of 10, Very Good, (1)
"The house itself was clean. Had everything we needed. It seemed like the back yard was still being cleared of trees and debris. Was too chilly for sitting out though. All and all, was fine."
The price is AED 422
AED 526 total
includes taxes & fees
1 May - 2 May
Cozy 2-bedroom townhome in charming Elkton

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (159)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!

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

9.4 out of 10, Exceptional, (33)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at Ted’s property. The basement was cold as they hadn’t figured out to adjust the thermostat yet, so we didn’t spend any time down there. We also encountered challenges with the hot water heater, but overall it was a lovely stay. "
Amazing Waterfront Home on the Bush River

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

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

9.6 out of 10, Exceptional, (56)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.4 out of 10, Exceptional, (33)
"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

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

9.4 out of 10, Exceptional, (170)
"The lake house was spacious and had a beautiful view. The owner had a lot of amenities in the house available, so there was no need to run out for any supplies. Will book again!"
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (96)
"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! ...
Waterfront house with amazing views. Top of the Chesapeake
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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Other property types in Earleville

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (46)
"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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

10.0 out of 10, Exceptional, (35)
"Clean and away from all the hustle and bustle, not to mention the views and lovely hosts! Don’t miss out on this if you want a relaxing trip, or if you do want to explore the area there’s plenty of great small towns in the area, also an easy drive to some of the most iconic cities along the Chesapeake Bay."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.4 out of 10, Exceptional, (33)
"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
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.