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.

Guest favorite

Farm stay in Chestertown

4.94 out of 5 average rating, 106 reviews

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Apr 12 – 19

€ 241 per night
Guest favorite

Guest suite in Forest Hill

5.0 out of 5 average rating, 107 reviews

Scenic, private 2 room-guest suite, near Bel Air

Relax and enjoy the scenic view of the countryside in this spacious (3 room) guest suite. The sunset is gorgeous! Spend the weekend enjoying the local activities: Dance under the stars at Boordy Vineyard Taste the craft beers at local breweries Hiking at Rocks State Park Biking nearby at the old railroad trail Explore the shops and restaurants on Main Street in historic Bel Air Spend a work trip in this peaceful, quiet space, located close to Aberdeen Proving Grounds, Peach Bottom Plant.

Feb 2 – 9

€ 104 per night
Guest favorite

Guesthouse in Media

4.96 out of 5 average rating, 467 reviews

Studio Apartment in Attractive Sylvan Setting

Enjoy the view of the treetops outside this secluded and bright studio while listening to limitless free music on the smart speaker. Unique touches include exposed beams, sliding barn door and European-style bathroom with large tiled shower. Enjoy original artwork hanging on the walls, a nod to Philadelphia's thriving art scene. Designed and decorated using a combination of American & European influences, the high quality finishes and accessories make this 280 square foot space feel like home.

Aug 11 – 18

€ 115 per night

Popular amenities for Galena vacation rentals

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

Guest favorite

Apartment in Clayton

4.95 out of 5 average rating, 40 reviews

Quaint 1 BR apt in Historic Firehouse

Sep 6 – 13

€ 104 per night
Guest favorite

Apartment in Dover

4.88 out of 5 average rating, 84 reviews

Cozy apartment in a quiet Amish country setting

Feb 1 – 8

€ 89 per night
Guest favorite

Home in Millington

4.91 out of 5 average rating, 32 reviews

The Peaceful Getaway (with private pool & hot tub)

Jul 5 – 12

€ 451 per night
Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 43 reviews

Long Beach Cottage, (romantic couple’s getaway)

Nov 26 – Dec 3

€ 464 per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Feb 3 – 10

€ 156 per night
Guest favorite

Apartment in Kent County

4.92 out of 5 average rating, 73 reviews

Furnished country apartment!

Oct 24 – 31

€ 101 per night
Guest favorite

Home in Greensboro

4.95 out of 5 average rating, 44 reviews

Cozy 2 bedroom home on wooded private lane

Feb 5 – 12

€ 125 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

€ 525 per night
Guest favorite

Apartment in Chesapeake City

4.95 out of 5 average rating, 63 reviews

hygge haven: hygge= happy + cozy

May 30 – Jun 6

€ 134 per night
Guest favorite

Home in Kennedyville

4.91 out of 5 average rating, 45 reviews

Comfy and Cozy on the Eastern Shore

Sep 14 – 21

€ 185 per night
Guest favorite

Home in Millington

4.91 out of 5 average rating, 11 reviews

Lark's Nest on the Chester River

Sep 26 – Oct 3

€ 231 per night
Guest favorite

Cottage in Earleville

4.98 out of 5 average rating, 56 reviews

The Bohemia Charmer

Sep 10 – 17

€ 292 per night

Destinations to explore

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  3. Maryland
  4. Kent County
  5. Galena