Vacation rentals in Galena

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Top-rated vacation rentals in Galena

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Guest favorite

Guest suite in Smyrna

4.82 out of 5 average rating, 113 reviews

King's Landing, Simple & Unique

Our charming home, built circa 1800's, updated with addition's in the 1930's and brought into the 21st century, totally revamped and modernized, 2020. Located within walking distance of downtown Historical Smyrna, where charming pubs and stores await you. Enter your quarters, through the 'Milk Room', pass your private full bath, by the spiral staircase to your spacious private bedroom suite, nestled below a cathedral ceiling on the second floor. Oh, Dover Downs and Wesley college are close by

Sep 27 – Oct 4

ﺩ.ﺇ548 per night

Superhost

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.

Jun 18 – 25

ﺩ.ﺇ519 per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 129 reviews

Chestertown - Eastern Shore Getaway

"A little slice of Americana" (commented one of our guests) This century-old three-story home is in the beautiful historic district of Chestertown, which sits on the majestic, unspoiled Chester River, on Maryland's famous Eastern Shore. We are right across the street from Washington College and just blocks from the quaint ambiance of High Street. The commercial district is equally accessible, with banks, grocery and liquor stores, restaurants, and more, a few blocks up Washington Avenue.

Oct 5 – 12

ﺩ.ﺇ501 per night

Guest favorite

Apartment in Greenwood

4.97 out of 5 average rating, 477 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Nov 20 – 27

ﺩ.ﺇ302 per night

Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 102 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Jan 20 – 27

ﺩ.ﺇ500 per night

Guest favorite

Apartment in Frederica

4.96 out of 5 average rating, 257 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

Oct 29 – Nov 5

ﺩ.ﺇ267 per night

Guest favorite

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.

Oct 1 – 8

ﺩ.ﺇ514 per night

Guest favorite

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.

Mar 11 – 18

ﺩ.ﺇ406 per night

Guest favorite

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.

Mar 29 – Apr 5

ﺩ.ﺇ381 per night

Guest favorite

Apartment 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.

May 3 – 10

ﺩ.ﺇ477 per night

Guest favorite

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.

Apr 22 – 29

ﺩ.ﺇ375 per night

Superhost

Cottage in Galena

4.83 out of 5 average rating, 103 reviews

Tranquil and relaxing escape at Morton Hall

Totally refreshed 2021! Enjoy the peaceful, rural setting of this unique telescoping house. Set in acres of farmland, this quiet and tranquil home helps you to unplug and relax. Take a walk down the street to the Sassafras river or explore the local area.

Feb 10 – 17

ﺩ.ﺇ485 per night