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Vacation rentals in Galena

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Top-rated vacation rentals in Galena

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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.

Aug 7 – 14

G$28,311 GYD per night

Guest suite in Chestertown

4.99 out of 5 average rating, 130 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.

Sep 12 – 19

G$28,067 GYD per night

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)

Sep 19 – 26

G$17,163 GYD per night

Guesthouse in White Marsh

4.97 out of 5 average rating, 140 reviews

Bird River Bottega - A Waterfront Oasis!

Private entrance studio located on a waterfront property. The Bottega is perfect for couples, solo travelers, and business professionals; best suited for two travelers. Enjoy your morning coffee by the water and watch the Ospreys, herons, ducks, hawks, and bald eagles galore. Whether you are fishing, lounging, or kayaking the Bird River (home to the Chesapeake Bay), you are bound for relaxation. Surrounded by a plethora of eateries, shopping, and entertainment all within a 25 minute drive.

Dec 15 – 22

G$18,818 GYD per night

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 18 – 25

G$28,448 GYD per night

Apartment in Frederica

4.97 out of 5 average rating, 258 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!

Sep 11 – 18

G$13,574 GYD per night

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

G$29,265 GYD per night

Cottage in North East

4.97 out of 5 average rating, 437 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 18 – 25

G$23,073 GYD per night

Cottage in North East

4.94 out of 5 average rating, 279 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.

Jan 8 – 15

G$20,452 GYD per night

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.

Jul 28 – Aug 4

G$27,297 GYD per night

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.

Jun 12 – 19

G$21,625 GYD per night

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.

Aug 5 – 12

G$27,591 GYD per night

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Popular amenities for Galena vacation rentals

Free parking on premises

Air conditioning

Stay near Galena's top sights

Twinny's Place9 locals recommend

Galena Pizzaria Inc4 locals recommend

Cross Street Food and Garden6 locals recommend

Other great vacation rentals in Galena

Apartment in Worton

5.0 out of 5 average rating, 16 reviews

Elliott House Historic Home Near Chesapeake Bay

Apr 30 – May 7

G$35,032 GYD per night

Apartment in Dover

4.87 out of 5 average rating, 87 reviews

Cozy apartment in a quiet Amish country setting

Aug 22 – 29

G$19,583 GYD per night

Apartment in Clayton

4.93 out of 5 average rating, 41 reviews

Quaint 1 BR apt in Historic Firehouse

May 27 – Jun 3

G$22,135 GYD per night

Home in Millington

4.91 out of 5 average rating, 11 reviews

Lark's Nest on the Chester River

Nov 29 – Dec 6

G$45,734 GYD per night

Home in Millington

4.91 out of 5 average rating, 34 reviews

The Peaceful Getaway (with private pool & hot tub)

Dec 15 – 22

G$82,168 GYD per night

Home in Betterton

5.0 out of 5 average rating, 17 reviews

Ruby's Sea Glass Cottage near Betterton Beach

Dec 26 – Jan 2

G$45,894 GYD per night

Home in Greensboro

4.96 out of 5 average rating, 46 reviews

Cozy 2 bedroom home on wooded private lane

Oct 10 – 17

G$26,818 GYD per night

Apartment in Chestertown

5.0 out of 5 average rating, 67 reviews

Waterfront historic district 1BR Apartment

Jul 22 – 29

G$34,419 GYD per night

Destinations to explore