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Vacation Homes in Galena

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (260)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (160)
"The property was great, clean and spacious. The views were remarkable and amenities exactly what we needed while we are working a major event."
Chesapeake Bay House with Dock & Private Beach

3 Mi to Dtwn: Townhome w/ Deck in Dover

3 Mi to Dtwn: Townhome w/ Deck in Dover

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (18)
"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

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (14)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

9.4 out of 10, Exceptional, (3)
"Nice and quiet place to stay"
The price is SAR 656
SAR 1,244 total
includes taxes & fees
30 Jun - 1 Jul
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (97)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake

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

9.6 out of 10, Exceptional, (39)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"The place is well cared and cute. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (77)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
Luxury 2-bedroom house with Water views, Chesapeake City

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (18)
"Everyone in our family ages 8, 10, 17, 18, 38, 64, and 71 thought the house and location were perfect and we had a great stay."
Chesapeake City Quiet Overlook

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

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

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

10.0 out of 10, Exceptional, (13)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.4 out of 10, Exceptional, (46)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is SAR 1,212
SAR 2,286 total
includes taxes & fees
17 Jun - 18 Jun
5-bedroom vacation home 5 minutes from historic Charlestown

Spacious North East Home w/ Fenced Yard & Fire Pit

10.0 out of 10, Exceptional, (8)
"Very nice house and well suited for the four adult couples on this trip."
Spacious North East Home w/ Fenced Yard & Fire Pit

Waterfront family resort Lodge with private pier, game room and bar

9.8 out of 10, Exceptional, (27)
"We had a great time. Place was unique and good for group get together. "
Waterfront family resort Lodge with private pier, game room and bar

Waterfront House on the Upper Chesapeake Bay

9.0 out of 10, Wonderful, (4)
"My boyfriend and i had a great 2 days! So peaceful bing on the water. Cottage was equipped with everything you would need!"
Waterfront House on the Upper Chesapeake Bay
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.
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