Photo by Lisa Warmouth Strusowski

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Compare 146 Vacation Homes in Earleville with updated reviews, rates, and availability.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (258)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Beautiful Colonial Style Home in Nottingham PA

9.6 out of 10, Exceptional, (10)
"Wonderful experience in a beautiful home. Could live there! Perfect for our entire family. Appreciate how well appointed it was with supplies, linens, etc. Could have used one more bathroom but it didn't cramp our style. Thanks to the host for a memorable vacation! "
Beautiful Colonial Style Home in Nottingham PA

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

The price is SAR 507
SAR 1,066 total
includes taxes & fees
20 Apr - 21 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)
"This 3 bedroom, 2 bath Cottage was perfect! Our family enjoyed staying there. We found the home to be clean, well equipped and comfortable."
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)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is SAR 1,347
SAR 2,430 total
includes taxes & fees
8 May - 9 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)
"We really enjoyed our stay here ! Plenty of space to spread out for everyone . We will rent this home again next year when we come to town ! "
The price is SAR 619
SAR 1,313 total
includes taxes & fees
21 Apr - 22 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)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
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)
"The house had plenty of space and location was great!"
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)
"The home was perfect for our family of 10. We spent most of our time on the beautiful screened in porch overlooking the river. The location was within a 5 min drive to all our favorite restaurants. The owners are very accommodating and quick to answer any questions. "
The price is SAR 2,115
SAR 4,152 total
includes taxes & fees
24 Apr - 25 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 home had to have been the most perfect VRBO we have stayed in. The home was clean, comfortable, stocked with amenities that made the stay incredibly pleasant and in a fantastic location. We particularly enjoyed the built in speakers in the dining room. I would highly recommend this home for a visit to Chestertown. "
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 SAR 432
SAR 537 total
includes taxes & fees
9 May - 10 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)
"This was a great Property, with a Great View. Wife & her sister, and 98yr old Mother really enjoyed it."
Nancy’s Touch, A Waterfront Paradise!

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

9.4 out of 10, Exceptional, (33)
"Clean with comfortable beds!"
Waterfront Oasis w/ Private Dock, 3BR/2BA

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"Wonderful place to 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, (55)
"Host was excellent making sure we had everything we needed and more for a comfortable stay. The home was very cozy and comfortable like being in your own home. We will definitely be returning! "
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)
"Very spacious and relaxing and well kept. We really enjoyed our stay."
*** 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, (95)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
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)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
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)
"Great location, wonderful place and fantastic owner. Recommendations on restaurants and things to do were perfect. We had a great time and Betty Ann was very kind and responsive in communications. Will definitely visit again!"
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.