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Earleville Holiday Rentals

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Holiday Rentals in Earleville

Cottage in Port Deposit

10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AU$354
includes taxes & fees
5 Jan - 6 Jan 2026
Quarry Landing - Center of Town & River View - 3 Bedroom

Cottage in Port Deposit

10.0 out of 10, Exceptional, (31)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is AU$319
includes taxes & fees
9 Dec - 10 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Apartment in Elkton

2.0 star property
9.8 out of 10, Exceptional, (7)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is AU$246
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Apartment in Chesapeake City

2.0 star property
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is AU$510
includes taxes & fees
9 Dec - 10 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cabin in Chesapeake City

9.0 out of 10, Wonderful, (19)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is AU$424
includes taxes & fees
9 Dec - 10 Dec
Historic Chesapeake City Stay

Holiday Home in Bel Air

10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
The price is AU$477
includes taxes & fees
16 Dec - 17 Dec
Small House on Gentleman’s Farm

Apartment in Newark

2.0 star property
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay."
United States
Erik H.
The price is AU$422
includes taxes & fees
9 Dec - 10 Dec
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Apartment in Millington

9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$191
includes taxes & fees
9 Dec - 10 Dec
Guest Suite for up to 2 in a Victorian on the Chester River

Apartment in Chestertown

9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$242
includes taxes & fees
9 Dec - 10 Dec
First Floor Studio Apartment in Historic Chestertown

Holiday Home in Smyrna

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$544
includes taxes & fees
13 Dec - 14 Dec
Amazing Modern house with a full kitchen and parking

Apartment in Elkton

9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is AU$171
includes taxes & fees
15 Dec - 16 Dec
Country Get Away 1 Bedroom Apartment

Holiday Home in Elkton

10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AU$520
includes taxes & fees
9 Dec - 10 Dec
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Apartment in Bear

9.6 out of 10, Exceptional, (4)
"Second time staying in as many weeks. Place is spot on for what we needed for our quick trips. Close to food and shopping as well as easy access to highways if needed."
United States
Jeffrey R.
The price is AU$178
includes taxes & fees
9 Dec - 10 Dec
Cozy loft above ink shop

Cottage in Charlestown

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
The price is AU$591
includes taxes & fees
9 Dec - 10 Dec
Long Beach Cottage, (romantic couple’s getaway)

Holiday Home in Elkton

9.6 out of 10, Exceptional, (5)
"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."
United States
Rees L.
The price is AU$240
includes taxes & fees
9 Dec - 10 Dec
Summer Rustic Camping with AC and King Bed

Apartment in Worton

10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is AU$474
includes taxes & fees
9 Dec - 10 Dec
Waterfront Retreat with Private Dock and Beach

Holiday Home in Bel Air

10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
The price is AU$451
includes taxes & fees
9 Dec - 10 Dec
Hobbit House one of a kind home

Holiday Home in Elkton

8.0 out of 10, Very good, (10)
"Nice and quiet place to stay"
United States
Gary M.
The price is AU$428
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Apartment in Port Deposit

10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
The price is AU$392
includes taxes & fees
9 Dec - 10 Dec
Private 3 room Queen Suite w/Kitchenette

Holiday Home in Newark

9.4 out of 10, Exceptional, (20)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is AU$561
includes taxes & fees
30 Dec - 31 Dec
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
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 Earleville Hotel Reviews

Find out more about Earleville

Everything you need to know about Earleville holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Earleville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Earleville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Earleville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Earleville. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Earleville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Earleville holiday rentals we have selected for you start as low as AU$240 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Earleville rentals

At Expedia, we put the best Earleville holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Earleville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Earleville holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Earleville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Earleville?

Yes, there are holiday rentals close to the most popular sights in Earleville, or you can select a more secluded option if you're looking for a relaxing stay. Earleville is known for its museums.

What are some of the best holiday rentals that Earleville has to offer?

Waterfront Lodge packed with Amenities: This highly rated holiday home rental in Earleville is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Earleville?

Expedia has 5 holiday rentals for your stay in Earleville.

What can I see and do in Earleville?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Earleville Wildlife Management Area and Skipjack Cove Yachting Resort are other places to visit while you're in town.

What are holiday rentals like in Earleville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Earleville. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.