Search Vacation Homes in Galena

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Galena

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (165)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (13)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is AED 724
AED 1,636 total
includes taxes & fees
11 Aug - 12 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (269)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience

Walk to Town & River: Charming Home in North East!

10.0 out of 10, Exceptional, (2)
"Great stay and responsive host. So definitely stay again. "
Walk to Town & River: Charming Home in North East!

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "
Luxury 2-bedroom house with Water views, Chesapeake City

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (72)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (99)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (55)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (10)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (23)
"Was a great clean place located in a nice little town! Would definitely recommend it!"
Tip Of The Town Fresh and New 3 Bedroom Nest

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (20)
"We attended a wedding across the canal from this house at the Chesapeake Inn. It was very cool to see these really large ships go by as we sat on the deck. Very nice accommodations here! Jane was a great host!"
Chesapeake City Quiet Overlook

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Waterfront Estate w Private Pier, Game Room & Bar

9.8 out of 10, Exceptional, (30)
"Overall, our stay was fantastic. The weather was absolutely magnificent the entire stay."
Waterfront Estate w Private Pier, Game Room & Bar

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (15)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Galena Hotel Reviews