Galena Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Galena

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

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

9.6 out of 10, Exceptional, (8)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm
Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip."
Chesapeake Bay House with Dock & Private Beach
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, (33)
"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.
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)
"Everything about this rental was easy, from check in to departure. We had one challenge with the TV and the host answered my text immediately and solved the issue for us. House was clean and as described in the listing. Highly recommend. "
Waterfront house with amazing views. Top of the Chesapeake
Historic Chesapeake City Stay
Marina

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
$263 nightly
The price is $279
Oct 2 - Oct 3
Total with taxes and fees
Historic Chesapeake City Stay
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, (57)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Nancy’s Touch, A Waterfront Paradise!
Terrace/patio

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (169)
"Absolutely fantastic place to stay. When we walked in, it just felt so comfortable. The gardens are beautiful and we were able to see Eagles most every day. Communication was excellent. "
Nancy’s Touch, A Waterfront Paradise!
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, (48)
"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
Outdoor Oasis + Hot Tub: Maryland Home w/ Bar!
Terrace/patio

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

7.4 out of 10, Good, (3)
"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!
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (276)
"We had such a great weekend at this property. It was beautiful and such a relaxing location. House had everything we needed. We hope to be back!! "
Captivating Chesapeake experience
5-bedroom vacation home 5 minutes from historic Charlestown
Sun loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (144)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
$571 nightly
The price is $605
Oct 8 - Oct 9
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
Tiny Home Tranquil Oasis
Fridge, microwave, oven, stovetop

Tiny Home Tranquil Oasis

$233 nightly
The price is $242
Oct 2 - Oct 3
Total with taxes and fees
Tiny Home Tranquil Oasis
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (9)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (101)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
$144 nightly
The price is $159
Oct 6 - Oct 7
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

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

9.8 out of 10, Exceptional, (10)
"We thoroughly enjoyed this cottage and location for weekend during lacrosse tournaments. Much better than staying in hotel and perfect on the water to enjoy some family time! Thanks Angela! "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
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, (23)
"Peaceful relaxing getaway with my family. The cottage was perfect in every way. The property outside was a dream. Every day we were outside on the deck or dock enjoying nature. This is exactly what we needed to recharge with life. Can’t wait to come back and enjoy this perfect retreat again! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Marina

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Terrace/patio

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

9.8 out of 10, Exceptional, (84)
"We had a wonderful weekend. Thank you!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Property grounds

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (12)
"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
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Galena Hotel Reviews

Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

10/10 Excellent
"The place is peaceful and nict workers"
comfort. 1-night trip
Posted 19 hours ago
Red Roof Inn & Suites Dover Downtown

Find out more about Galena

Find out more about Galena

Everything you need to know about Galena vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Galena vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Galena vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Galena vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Galena. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Galena in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $159 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Galena rentals

At Expedia, we put the best Galena vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Galena rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Galena vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Galena. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Galena?

Yes, we offer vacation rentals close to well known points of interest in Galena, or you can select a secluded option if you're looking for relaxation. Galena is known for its restaurants.

What are some of the best vacation rentals in Galena?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Galena is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Galena?

With 3 Expedia vacation rentals, you're sure 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 vacation rental in Galena like?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Galena. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips.