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Holiday Homes in Elkton

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Featured Holiday Homes in Elkton and around

Our top choices for Elkton holiday homes

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

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

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

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

Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

10.0 out of 10, Exceptional, (253)
"The pictures does no justice to this listing. It was absolutely beautiful and the stay was awesome. The hostbwas kind and generous. We had everything that we needed. Definitely would book again if I am going to be in the area. "
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

9.8 out of 10, Exceptional, (39)
"We had a great stay at this house while in town to celebrate our aunt's 90th birthday. The property was big enough to accommodate our 16 family members and we loved the historic charm. The busy road was a bit noisy but overall we had a wonderful time - thank you Vicki for a great experience!"
The price is €1,503
includes taxes & fees
11 Sept - 12 Sept
Vacay in an Authentic Chadds Ford / Brandywine Valley / Longwood Gardens

The Lodge at Cricklewood...where time melts away....

10.0 out of 10, Exceptional, (73)
"My family and I throughly enjoyed our short stay at Eric’s property. It a beautiful home in beautiful landscapes. The home is fully stocked and made our celebration of a graduation weekend memorable and successful. "
The Lodge at Cricklewood...where time melts away....

Homey Retreat in Historic Kennett Square!!

10.0 out of 10, Exceptional, (80)
"So convenient and easy to walk to shops and food! The house is adorable and clean. Looking forward to staying again. "
The price is €287
includes taxes & fees
2 Sept - 3 Sept
Homey Retreat in Historic Kennett Square!!

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

Cozy Farmhouse in Greenville, DE

10.0 out of 10, Exceptional, (24)
"Super clean house that’s perfect for a group gathering "
Cozy Farmhouse in Greenville, DE

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

2.0 star property
9.2 out of 10, Wonderful, (5)
"We had an excellent stay"
The price is €203
includes taxes & fees
2 Sept - 3 Sept
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

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 €571
includes taxes & fees
2 Sept - 3 Sept
5-bedroom vacation home 5 minutes from historic Charlestown

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!

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

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

9.2 out of 10, Wonderful, (179)
"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! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (165)
"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!

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

9.6 out of 10, Exceptional, (21)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is €270
includes taxes & fees
25 Aug - 26 Aug
Private townhouse near downtown and state park

Underground Railroad Barn

9.8 out of 10, Exceptional, (18)
"Great place to stay close to Longwood Gardens. We wanted to visit the Gardens, rated #1 botanical gardens in the United States. The barn was very convenient, spacious, modern. "
The price is €255
includes taxes & fees
25 Aug - 26 Aug
Underground Railroad Barn

Welcome to Woodview Estates!

7.6 out of 10, Good, (4)
"The house was perfect for our stay. We were in town for a family event and needed a place for 8 adults and 4 children and this was perfect. Lots of space to spread out with a great rec room that kept both kids and adults entertained during down time. The neighborhood was beautiful and had easy access to area restaurants and shopping. Close to many area attractions. It was the perfect location to have close proximity to points of interest and then return to at end of day to a relaxing...
Welcome to Woodview Estates!
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 Elkton Hotel Reviews