Photo by Lisa Warmouth Strusowski

Search Vacation Homes in Earleville

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Compare 159 Vacation Homes in Earleville with updated reviews, rates, and availability.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (260)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (18)
"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

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (160)
"The property was great, clean and spacious. The views were remarkable and amenities exactly what we needed while we are working a major event."
Chesapeake Bay House with Dock & Private Beach

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

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is SAR 536
SAR 1,070 total
includes taxes & fees
16 Jun - 17 Jun
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Cozy 2-bedroom townhome in charming Elkton

8.8 out of 10, Excellent, (3)
"This home wss a perfect stay for me and my friends, spacious, clean, and as described "
The price is SAR 431
SAR 537 total
includes taxes & fees
18 Jun - 19 Jun
Cozy 2-bedroom townhome in charming Elkton

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

9.6 out of 10, Exceptional, (14)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (97)
"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

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

10.0 out of 10, Exceptional, (12)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (17)
"Wonderful experience, thank you for having us!! "
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

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

9.6 out of 10, Exceptional, (38)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"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

Summer Rustic Camping with AC and King Bed

10.0 out of 10, Exceptional, (3)
"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 SAR 306
SAR 611 total
includes taxes & fees
2 Jun - 3 Jun
Summer Rustic Camping with AC and King Bed

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (18)
"Everyone in our family ages 8, 10, 17, 18, 38, 64, and 71 thought the house and location were perfect and we had a great stay."
Chesapeake City Quiet Overlook

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

10.0 out of 10, Exceptional, (77)
"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!

Modern cozy get-away* game room-amish country

Modern cozy get-away* game room-amish country

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

The Cozy Corner, 2-bedroom townhome in charming Newark with WiFi, and parking

10.0 out of 10, Exceptional, (1)
"Mohammed was such an amazing host to us, even before we checked in! We were a little early & saw him prior to check-in, he assured us whatever we may need don’t hesitate to give him a call. The location was great, very easy to get to other places in a nice quiet neighborhood. The entire house was comfortable and nicely decorated. Mohammed is such a great host that at checkout we were still cleaning a little and he let us stay until 1pm free of charge even with another guest coming after us!!!...
The Cozy Corner, 2-bedroom townhome in charming Newark with WiFi, and parking

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

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

9.4 out of 10, Exceptional, (33)
"Quick stay so I could visit family in Abingdon and DC. So awesome. Beautiful property even with the raging wind and snow storm."
Waterfront Oasis w/ Private Dock, 3BR/2BA

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is SAR 1,347
SAR 2,449 total
includes taxes & fees
2 Jun - 3 Jun
5-bedroom vacation home 5 minutes from historic Charlestown
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.
Save an average of 15% on thousands of hotels when you're signed in