An aerial view of a marina surrounded by dense forest, with boats docked at the piers and a small building on the shore.

Earleville Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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
9.2 out of 10, Wonderful, (31 reviews)
"This is a great place, to feel comfortable. Exactly as advertised Just around the corner from Schaeffers."
United States
Janice H.
The price is AU$433
includes taxes & fees
25 Oct - 26 Oct
Historic Chesapeake City Stay
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

2. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$181
includes taxes & fees
2 Nov - 3 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
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, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is AU$161
includes taxes & fees
2 Nov - 3 Nov
Country Get Away Studio Apartment
Beach bar

4. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$466
includes taxes & fees
28 Oct - 29 Oct
Bohemia Manor Farm
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

5. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.4 out of 10, Exceptional, (6 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is AU$419
includes taxes & fees
26 Oct - 27 Oct
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

6. 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 AU$307
includes taxes & fees
2 Nov - 3 Nov
Beachcomber Suite
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

7. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AU$286
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove Room
A bedroom with a bed, a dresser, a mirror, and a door.

8. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is AU$490
includes taxes & fees
25 Oct - 26 Oct
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A garden path leading to a wooden building with a rustic appearance.

9. 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 AU$392
includes taxes & fees
25 Oct - 26 Oct
Secluded Cottage in Middle of Chestertown
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

10. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AU$687
includes taxes & fees
2 Nov - 3 Nov
5-bedroom vacation home 5 minutes from historic Charlestown
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

11. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is AU$577
includes taxes & fees
26 Oct - 27 Oct
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

12. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$229
includes taxes & fees
26 Oct - 27 Oct
First Floor Studio Apartment in Historic Chestertown
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.

13. 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 AU$135
includes taxes & fees
3 Nov - 4 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC
A wooden deck with lounge chairs and a dock extending into calm water.

14. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is AU$753
includes taxes & fees
28 Oct - 29 Oct
Waterfront house with amazing views. Top of the Chesapeake
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

15. 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
9.8 out of 10, Exceptional, (7 reviews)
"The host was great and easy to communicate with. It was a first time experience staying on a boat for my family and I and we really enjoyed it. Perfect for a few nights to visit family nearby."
United States
Jessica
The price is AU$409
includes taxes & fees
29 Oct - 30 Oct
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

16. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is AU$221
includes taxes & fees
2 Nov - 3 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

17. 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, (57 reviews)
"Unique charming place to relax."
United States
Nimia N.
The price is AU$302
includes taxes & fees
25 Oct - 26 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

18. 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, (3 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 AU$281
includes taxes & fees
25 Oct - 26 Oct
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

19. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"This is a very nice apt. The owner was very receptive to any questions we had, even allowed an early checkin."
United States
Kathleen B.
The price is AU$459
includes taxes & fees
25 Oct - 26 Oct
Private 3 room Queen Suite w/Kitchenette
A residential house with a brick exterior, a dark roof, and a front porch with a bench.

20. 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, (15 reviews)
"It is in a lovely neighborhood and the hosts were very welcoming of us and my 2 dogs. We were all very comfortable."
United States
Barb
The price is AU$260
includes taxes & fees
25 Oct - 26 Oct
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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

Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

10/10 Excellent
"Everything was perfect we have a good time Thank you See you soon 👍👍"
Mario 2-night trip
Posted 1 hour ago
Great Wolf Lodge Perryville

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$161 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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Earleville is located on a lake, and has a fireplace, 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 fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 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. 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.