Photo by Lisa Warmouth Strusowski

Earleville Holiday Rentals

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Holiday Rentals in Earleville

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (58)
"Lovely cottage, well-equipped, immaculately clean. "
United States
Mary
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Stunning waterfront villa with indoor pool and kids swing set and play area.
9.8 out of 10, Exceptional, (19)
"This was the perfect house for the occasion, the rooms were spacious and there was a lot of spaces to gather. We didn’t leave for the whole weekend and it was amazing. The property is beautiful and the lake is serene. Thanks for letting us stay! Would love to come back. "
United States
Kelly & Devin V.
Stunning waterfront villa with indoor pool and kids swing set and play area.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
9.8 out of 10, Exceptional, (51)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
United States
Lisa
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Chesapeake Bay House with Dock & Private Beach
10.0 out of 10, Exceptional, (174)
"Nice property. Large enough for 13. Plenty of space to spread out "
United States
Mike J.
Chesapeake Bay House with Dock & Private Beach
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (101)
"The river house has an absolutely amazing view! My kids were thrilled with the chance to fish off a very long dock and even get their feet in the water on a small beach below the house (when the tide was out). Overall, the house was perfect and just big enough for our large family of seven. Matt was very responsive to a few questions I had and was a wonderful host! "
United States
Skye M.
Waterfront house with amazing views. Top of the Chesapeake
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.4 out of 10, Exceptional, (36)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
United States
Vince E.
Waterfront Oasis w/ Private Dock, 3BR/2BA
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (12)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
10.0 out of 10, Exceptional, (27)
"Very nice cottage, as advertised"
United States
nick k.
The price is AU$324
includes taxes & fees
23 Oct - 24 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (10)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
United States
Michael S.
The price is AU$432
includes taxes & fees
26 Oct - 27 Oct
Historic Chesapeake City Stay
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.6 out of 10, Exceptional, (8)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (42)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
United States
Lexi F.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
5-bedroom vacation home 5 minutes from historic Charlestown
9.8 out of 10, Exceptional, (145)
" The location and the house! Great communication from owner!! Thank you!!"
United States
steve j.
The price is AU$932
includes taxes & fees
28 Oct - 29 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (24)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is AU$486
includes taxes & fees
2 Nov - 3 Nov
Waterfront Retreat with Private Dock and Beach
Tiny Home Tranquil Oasis
The price is AU$375
includes taxes & fees
2 Nov - 3 Nov
Tiny Home Tranquil Oasis
Summer Rustic Camping with AC and King Bed
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$257
includes taxes & fees
22 Oct - 23 Oct
Summer Rustic Camping with AC and King Bed
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.6 out of 10, Exceptional, (34)
"We loved our stay. Our family wants us to book again next year. Thank you"
United States
Darlene G.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (103)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AU$247
includes taxes & fees
23 Oct - 24 Oct
First Floor Studio Apartment in Historic Chestertown
Quarry Landing - Center of Town & River View - 3 Bedroom
9.8 out of 10, Exceptional, (9)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
United States
Elise E.
The price is AU$350
includes taxes & fees
20 Nov - 21 Nov
Quarry Landing - Center of Town & River View - 3 Bedroom
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
9.8 out of 10, Exceptional, (6)
"This property was amazing! My family of six, really enjoyed the pool, large yard, for one including a balcony, toys for the kids, and many more! Will definitely be staying again in the future"
United States
serina
The price is AU$2,087
includes taxes & fees
22 Oct - 23 Oct
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
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$247 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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Earleville is located on the beach, 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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?

Chesapeake Bay and Earleville Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. Cecilton Park and Hack's Point Marina 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.