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

Earleville Vacation Rentals

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Check prices for these dates

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

Our top choices for Earleville vacation 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.
$263 nightly
The price is $279
Oct 25 - Oct 26
Total with taxes and fees
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
$118 nightly
The price is $125
Oct 22 - Oct 23
Total with taxes and fees
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, (51 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
$105 nightly
The price is $111
Oct 28 - Oct 29
Total with taxes and fees
Country Get Away Studio Apartment
A bedroom with a single bed, a wooden wardrobe, and a ceiling light.

4. 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
$275 nightly
The price is $292
Nov 5 - Nov 6
Total with taxes and fees
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.

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.
$197 nightly
The price is $214
Oct 26 - Oct 27
Total with taxes and fees
Beachcomber Suite
A brick house with a front porch, a chimney, and a well-maintained lawn.

6. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
$352 nightly
The price is $373
Oct 27 - Oct 28
Total with taxes and fees
Bohemia Manor Farm
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
$183 nightly
The price is $199
Oct 26 - Oct 27
Total with taxes and fees
Turtle Cove Room
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

8. 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.
$144 nightly
The price is $159
Oct 22 - Oct 23
Total with taxes and fees
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.

9. 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
$88 nightly
The price is $93
Oct 27 - Oct 28
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
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.
$471 nightly
The price is $499
Oct 27 - Oct 28
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
A wooden deck with lounge chairs and a dock extending into calm water.

11. 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.
$470 nightly
The price is $498
Oct 22 - Oct 23
Total with taxes and fees
Waterfront house with amazing views. Top of the Chesapeake
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.

12. 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.
$428 nightly
The price is $447
Oct 26 - Oct 27
Total with taxes and fees
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

13. 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.
$145 nightly
The price is $154
Nov 2 - Nov 3
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

14. 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.
$264 nightly
The price is $274
Oct 25 - Oct 26
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Exterior

15. 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.
$193 nightly
The price is $194
Oct 22 - Oct 23
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A covered deck area with a grill and outdoor seating.

16. 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
$226 nightly
The price is $235
Oct 22 - Oct 23
Total with taxes and fees
Nature's Haven Tiny Home
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

17. 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.
$310 nightly
The price is $329
Oct 22 - Oct 23
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

18. 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
$285 nightly
The price is $296
Oct 24 - Oct 25
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A kitchen with white cabinets, a wooden countertop, a built-in oven, and a window.

19. Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (18 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$218 nightly
The price is $231
Nov 9 - Nov 10
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

20. 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.
$199 nightly
The price is $210
Oct 22 - Oct 23
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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

Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

8/10 Good
"The room was clean. The air conditioner wasn't the greatest and one of the stairs was loose and almost killed me. But other than that it was fine. Breakfast was good!"
Denise 8-night trip
Posted 3 hours ago
Sonesta ES Suites Wilmington - Newark

Find out more about Earleville

Everything you need to know about Earleville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Earleville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Earleville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Earleville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Earleville rentals

At Expedia, we put the best Earleville vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Earleville?

Yes, you can find vacation rentals near popular sights in Earleville, or you can choose a more remote option if you want a relaxing place to stay. Earleville is known for its museums.

What's the top vacation rental that Earleville has to offer?

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental near Earleville is located on a lake and has a fireplace, a garden, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

How many vacation rentals are there in Earleville?

Expedia has 5 vacation 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 vacation rentals like in Earleville?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Earleville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.