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Holiday rentals in Earleville

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Top-rated holiday rentals in Earleville

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Cottage in Betterton

4.8 out of 5 average rating, 51 reviews

Cottage By the Chesapeake

This cozy cottage on the Eastern Shore of Maryland sits on a spacious private lot a five minute walk to Betterton Beach! Relax on the screened-in porch or fully-furnished living room after a day in the woods, or cook a homemade dinner in our fully-equipped kitchen. The community of Betterton offers tennis courts, covered outside picnic tables with grills, a brand new playground, and of course...THE BEACH! For a change of pace or a night out, Chestertown, Maryland is only a short drive away.

18–25 Jun

€ 154 per night

Guest favourite

Flat in Havre de Grace

5.0 out of 5 average rating, 138 reviews

Mid Century 2 Bedroom at JoRetro with a King Bed

Enjoy a newly renovated mid-century modern apartment in the heart of downtown Havre de Grace, located above our shop, JoRetro Vintage Market. We currently have 3 units to choose from. We have decorated this suite using the 1945 Pyrex Primary bowls for design inspiration. Find luxury amenities and authentic Vintage items throughout the apartment, including Pyrex! Walk to restaurants and unique shops. Visit the lighthouse and museums. Enjoy a show at the Opera House or the State Theater.

19–26 Mar

€ 172 per night

Home in Earleville

4.89 out of 5 average rating, 35 reviews

Waterfront Estate with Pool on 16 acres

Looking for a place to enjoy a water front estate on 16 acres of land? Look no further than Cherry Grove Manor. It is a traditional style home that sleeps 18 & features 6,000 sq. ft. on 3 levels of living. Enjoy your private 550 ft. sandy beach that overlooks the mouth of the Elk River with views into the Chesapeake Bay. There is a private dock that you can fish and crab from. The newly renovated Salt Water Pool (not heated) offers views of the water. (Pool available May-September. )

6–13 Dec

€ 1,145 per night

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

1–8 Oct

€ 149 per night

Guest favourite

Cottage in North East

4.97 out of 5 average rating, 436 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.

11–18 Mar

€ 116 per night

Guest favourite

Cottage in Earleville

4.98 out of 5 average rating, 58 reviews

The Bohemia Charmer

Take it easy at this unique and tranquil getaway. In the Hack's Point Community, on the shores of the Bohemia River, this home will give you plenty of opportunities to relax, no matter the season. This home has the closest proximity to the community beach and pier, and it also exudes historic charm with a stunning 2-story fireplace, hardwood & stone flooring, and built-ins. ***There is no guest access to the pier for storage or day-use of boats***

10–17 Sep

€ 300 per night

Guest favourite

Home in Earleville

4.91 out of 5 average rating, 151 reviews

Cozy 4 BR 3 BA Near Chesapeake City

Peaceful, cozy modern cottage with many amenities in a water-oriented community along the Bohemia River. Just minutes from Chesapeake City and located across the street from the water. Our house is perfect for family vacations, tranquil retreats, girl/guy getaways, weddings, wedding guests. Two queen master BR’s w/private baths on the first floor, second floor has one larger BR w/twins and smaller BR w/daybed +trundle and shared bathroom.

17–24 Oct

€ 307 per night

Guest favourite

Cottage in North East

4.94 out of 5 average rating, 276 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

29 Mar – 5 Apr

€ 115 per night

Guest favourite

Flat in Chesapeake City

4.93 out of 5 average rating, 141 reviews

Bohemia Vista CC Horse Farm Apartment

Comfortable and private, 10 minutes from Chesapeake City This private apartment comes with a basic kitchen, private bedroom with king sized bed, common area twin bed, sitting area, bath with a jacuzzi tub, and expansive views of farmland and horses. Private entrance and use of private laundry room included.

3–10 May

€ 138 per night

Home in Earleville

4.92 out of 5 average rating, 38 reviews

Veazey Cove | Waterfront w/ Pool + Hot Tub!

BNB Breeze Presents: Veazey Cove! Veazey Cove has everything needed to be the retreat destination of your DREAMS! Everyone in your group will find something to enjoy, such as: ★ Waterfront Views ★ HOT TUB! ★ Pool ★ 8,000 sq. Feet! ★ Outdoor Patio ★ Game Room! ★ Pool Table ★ Private Dock and much more!

9–16 Jan

€ 1,176 per night

Guest favourite

Guest suite in North East

4.95 out of 5 average rating, 116 reviews

The Cozy Studio of North East MD

Newly remodeled second floor unit in the town of North East and walking distance to restaurants, shops. This unit sleeps 4 and has an attached full bath and an eat-in kitchenette. BRING YOUR BOAT! This unit is walking distance to the water and has ample street parking for your boat.

22–29 Apr

€ 103 per night

Guest favourite

Home in North East

4.9 out of 5 average rating, 122 reviews

Private home

Our guest house has been renovated and is located next to the main house on the property. You will have a private drive, and parking area. Great for boaters! We are 3 miles to town, and rivers. 15 minutes to Delaware. And the university of delaware

1–8 Dec

€ 119 per night

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Popular amenities for Earleville holiday rentals

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Other great holiday rentals in Earleville

Guest favourite

Flat in Chesapeake City

4.94 out of 5 average rating, 64 reviews

cozy garden: hygge= happy + cozy

17–24 Nov

€ 145 per night

Guest favourite

Home in Elkton

5.0 out of 5 average rating, 24 reviews

Elk River Cottage

21–28 Jul

€ 268 per night

Guest favourite

Flat in Rising Sun

4.91 out of 5 average rating, 53 reviews

Cozy Corner Getaway: Relax on an Amish Farm

17–24 Mar

€ 100 per night

Guest favourite

Cottage in Charlestown

4.98 out of 5 average rating, 49 reviews

Long Beach Cottage, (romantic couple’s getaway)

17–24 Sep

€ 487 per night

Guest favourite

Flat in Clayton

4.93 out of 5 average rating, 41 reviews

Quaint 1 BR apt in Historic Firehouse

16–23 Jul

€ 107 per night

Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 28 reviews

Charming, updated home in Historic Chesapeake City

3–10 Nov

€ 428 per night

Guest favourite

Home in North East

4.95 out of 5 average rating, 74 reviews

Red Point Lighthouse

27 Sep – 4 Oct

€ 911 per night

Guest favourite

Cottage in Chesapeake City

5.0 out of 5 average rating, 53 reviews

Bohemia Bungalow

13–20 Nov

€ 252 per night

Destinations to explore