Earleville Holiday Rentals from NZ$274: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Chesapeake City

Martha J.

includes taxes & fees

19 Oct - 20 Oct

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

Millington

Riley B.

includes taxes & fees

19 Oct - 20 Oct

A bunk bed room with white bedding and blue throw blankets.

3. Bohemia Manor Farm

Chesapeake City

includes taxes & fees

26 Oct - 27 Oct

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

Chesapeake City

includes taxes & fees

21 Oct - 22 Oct

A wooden cabin with a porch, surrounded by dense forest.

5. Country Get Away Studio Apartment

Elkton

JAMES V.

includes taxes & fees

22 Oct - 23 Oct

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

6. Beachcomber Suite

Kent County

"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...

Lisa E.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

7. Turtle Cove Room

Kent County

includes taxes & fees

9 Nov - 10 Nov

A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

8. 5-bedroom vacation home 5 minutes from historic Charlestown

Perryville

Teresa M.

includes taxes & fees

13 Oct - 14 Oct

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

Aberdeen

christine

includes taxes & fees

13 Oct - 14 Oct

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

10. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

includes taxes & fees

13 Oct - 14 Oct

11. Sunset River Shack -amazing waterfront view

Elkton

Natasha G.

A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

12. Long Beach Cottage, (romantic couple’s getaway)

Charlestown

Mike F.

includes taxes & fees

22 Oct - 23 Oct

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.

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

Charlestown

Sandy B.

includes taxes & fees

18 Oct - 19 Oct

A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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

Aberdeen

Matthew

includes taxes & fees

4 Nov - 5 Nov

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

Bear

"My boyfriend and I had a fantastic night on the yacht. We arrived right on time and found the AC and the lights on and ready for our arrival. I sunbathed on the front of the yacht and danced on the back after dinner at Grain H2O. The restaurant is located at the top of the hill on the marina . There was a band and we could hear the music from the boat. The marina was clean and everyone is friendly. At night it was very peaceful and easy to fall asleep. The morning we enjoyed our last couple of...

Karen

includes taxes & fees

16 Oct - 17 Oct

A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

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

Port Deposit

Terry R S.

includes taxes & fees

11 Oct - 12 Oct

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

Port Deposit

Don S.

includes taxes & fees

19 Oct - 20 Oct

A covered deck area with a grill and outdoor seating.

18. Nature's Haven Tiny Home

Bear

Maxwell

includes taxes & fees

22 Oct - 23 Oct

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

19. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

15 Oct - 16 Oct

A spacious living area with a dining table, sofa, and a kitchen in the background.

20. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

includes taxes & fees

21 Oct - 22 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

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

Ramada by Wyndham Newark/Wilmington

8/10 Good

"Good alignment between price and quality. Staff was fantastic. The breakfast is not good. The rooms are dated (but very clean, quiet, and comfortable!)... and the pricing reflects that, so I would still rate this hotel quite highly and would stay here again."

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10/10 Excellent

"Property was incredibly clean, comfortable, and exactly as described. The host was absolutely wonderful—very pleasant and incredibly easy to reach. Whenever we sent a text, her response was incredibly fast, which made our stay completely stress-free. We had a great time and would definitely stay here again!""

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

10/10 Excellent

"We had a wonderful long weekend at the cottage. It is beautifully decorated and very clean. It was perfect for our needs. We spent our days boating on the upper bay (gorgeous weather) and evenings relaxing on the deck with a perfect view of the sunset and turkey point lighthouse. Thank you Chris and we would love to come back next season."

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$274 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?

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Earleville holiday rentals

1. Historic Chesapeake City Stay

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

3. Bohemia Manor Farm

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

5. Country Get Away Studio Apartment

6. Beachcomber Suite

7. Turtle Cove Room

8. 5-bedroom vacation home 5 minutes from historic Charlestown

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

10. First Floor Studio Apartment in Historic Chestertown

11. Sunset River Shack -amazing waterfront view

12. Long Beach Cottage, (romantic couple’s getaway)

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

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

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

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

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

18. Nature's Haven Tiny Home

19. Secluded Cottage in Middle of Chestertown

20. Newly restored apartment in the heart of Chestertown

Find holiday rentals that suit your style

Top Earleville Hotel Reviews

Ramada by Wyndham Newark/Wilmington

Red Roof Inn & Suites Newark - University

La Quinta Inn & Suites by Wyndham Newark - Elkton

Holiday Inn Express & Suites Wilmington-Newark by IHG

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Find out more about Earleville

Frequently asked questions

Go further with the Expedia app