Galena Holiday Rentals

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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Holiday Rentals in Galena

Our top choices for Galena holiday rentals

Tip Of The Town Fresh and New 3 Bedroom Nest
Fridge, microwave, oven, stovetop

Tip Of The Town Fresh and New 3 Bedroom Nest

10.0 out of 10, Exceptional, (25)
"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
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
"Good experience"
The price is HK$1,558
HK$2,452 total
includes taxes & fees
16 Sept - 17 Sept
Charming 2-bedroom cabin close to Fair Hill on horse farm
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (62)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Sailor's Sunrise Cottage - Chesapeake Bay
Outdoor spa tub

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (52)
"It was represented very well. I would definitely recommend for getting away from crowds. NEAT place,yes you are at the water! Would give it a 4.7 overall.! "
Sailor's Sunrise Cottage - Chesapeake Bay
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (40)
"The house was perfect for 6 young adults! We were only 5 minutes from Anchor Marina which was perfect for our group. The fire pit and outdoor set up was nice and we had plenty of space for everyone. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is HK$771
HK$1,237 total
includes taxes & fees
24 Sept - 25 Sept
First Floor Studio Apartment in Historic Chestertown
Historic Chesapeake City Stay
Marina

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is HK$841
HK$2,172 total
includes taxes & fees
14 Sept - 15 Sept
Historic Chesapeake City Stay
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
Interior

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

10.0 out of 10, Exceptional, (1)
"The property is exactly as you see in the pictures/description. We were 4 adults, 4 kids (9 months to 13 years). Plenty of room for all of us. Hosts were quick to respond to any messages sent.Had a great 3 days here."
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"Great house, will stay again in the future. "
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Marina

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (31)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Beach nearby

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

9.8 out of 10, Exceptional, (18)
"Enjoyed our stay. Location is beautiful and peaceful! Great place for a large group."
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (22)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (46)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop

Tiny Home Tranquil Oasis

The price is HK$1,472
HK$1,881 total
includes taxes & fees
13 Sept - 14 Sept
Tiny Home Tranquil Oasis
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!

10.0 out of 10, Exceptional, (2)
"The house is amazing. Very clean and accessible. Carrie and Mike were amazing host . The backyard is truly an oasis. "
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (9)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Chesapeake City Quiet Overlook
Outdoor dining

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (21)
"We had a wonderful stay in Chesapeake City! The property was very clean, well stocked, and perfect for our family. The kitchen is gorgeous with a beautiful view of the water, and everything is labeled so items are easy to find and put away. Just a short walk to dinner at Schaefer’s Canal House and the trail. Highly recommend!"
Chesapeake City Quiet Overlook
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Excellent property and was exactly what we needed. It was clean, well maintained and easy to use."
Chesapeake Bay House with Dock & Private Beach
Waterfront house with amazing views. Top of the Chesapeake
Terrace/patio

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"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
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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Top Galena Hotel Reviews

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"."
Erin 1-night trip
Posted 1 day ago
Bally's Dover Casino Resort

Find out more about Galena

Find out more about Galena

Search for holiday rentals in Galena on Expedia! You can easily find your home rentals, villas, holiday apartments in Galena using one of the methods below:

  • View our selection of featured holiday rentals in Galena
  • Use the map to find apartments and other holiday homes in the Galena neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Galena while they last

Look no further and take a look at our great range of rental properties in Galena!

Frequently asked questions

Can I find a holiday rental in Galena?

Yes, there are holiday rentals close to the most popular sights in Galena, or you can select a more secluded option if you're looking for a relaxing stay. Galena is known for its restaurants.

What are some of the best holiday rentals that Galena has to offer?

Tip Of The Town Fresh and New 3 Bedroom Nest: This holiday home rental outside of Galena offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Galena?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Galena stay.

What’s there to see and do in Galena?

Explore the area and family-friendly sights such as Havre de Grace Maritime Museum, or get out into nature at a spot like Betterton Beach. Galena Town Hall and Sassafras Harbor Marina are other places to visit while you're in town.

What’s a holiday rental in Galena like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Galena. Holiday rentals feature amenities like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family gatherings.