Lodging Image

Earleville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Earleville holiday rentals

A riverside dock with boats, a covered seating area, and a bridge in the background.

1. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (28 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is NZ$468
includes taxes & fees
29 Aug - 30 Aug
Historic Chesapeake City Stay
A brick house with a front porch, a chimney, and a well-maintained lawn.

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is NZ$622
includes taxes & fees
9 Sept - 10 Sept
Bohemia Manor Farm
A wooden cabin with a porch, surrounded by dense forest.

3. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (47 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is NZ$186
includes taxes & fees
2 Sept - 3 Sept
Country Get Away Studio Apartment
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

4. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (27 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is NZ$209
includes taxes & fees
15 Sept - 16 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

5. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is NZ$326
includes taxes & fees
21 Sept - 22 Sept
Beachcomber Suite
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

6. Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$291
includes taxes & fees
21 Sept - 22 Sept
Turtle Cove Room
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

7. Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
9.8 out of 10, Exceptional, (51 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
The price is NZ$350
includes taxes & fees
27 Aug - 28 Aug
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

8. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is NZ$171
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house in Aberdeen with WiFi and AC
A covered deck area with a grill and outdoor seating.

9. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is NZ$381
includes taxes & fees
22 Sept - 23 Sept
Nature's Haven Tiny Home
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

10. Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is NZ$270
includes taxes & fees
6 Sept - 7 Sept
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

11. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (2 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
The price is NZ$313
includes taxes & fees
27 Aug - 28 Aug
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

12. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (3 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is NZ$482
includes taxes & fees
29 Aug - 30 Aug
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

13. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is NZ$401
includes taxes & fees
27 Aug - 28 Aug
Tiny Home Tranquil Oasis
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

14. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (123 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is NZ$266
includes taxes & fees
2 Sept - 3 Sept
First Floor Studio Apartment in Historic Chestertown
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

15. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is NZ$626
includes taxes & fees
9 Sept - 10 Sept
Waterfront Retreat with Private Dock and Beach
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

16. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"The Port Deposit area is a favorite "mini-vacation" location with great bars/restaurants and beautiful walks. We've stayed at this property a number of times and we've found the rooms to be perfect for our needs. "
United States
Lance W.
The price is NZ$477
includes taxes & fees
2 Sept - 3 Sept
Private 3 room Queen Suite w/Kitchenette
A house with a curved roof, a garden with various plants and flowers, and a red garage.

17. Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (11 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
The price is NZ$293
includes taxes & fees
27 Aug - 28 Aug
Cozy 1-bedroom bungalow in quaint Darlington with AC

18. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is NZ$469
includes taxes & fees
29 Aug - 30 Aug
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

19. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is NZ$573
includes taxes & fees
27 Aug - 28 Aug
Newly restored apartment in the heart of Chestertown
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

20. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (159 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$931
includes taxes & fees
22 Sept - 23 Sept
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Earleville Hotel Reviews

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

10/10 Excellent
"The hotel needs to remove the carpet."
Hassan 1-night trip
Posted 1 hour ago
Sonesta ES Suites Wilmington - Newark

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 favorite 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 depends 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 NZ$266 per night. Entering your travel dates in the search wizard you might find 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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Earleville is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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. Knight Island 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.