Galena Holiday Rentals

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Holiday Rentals in Galena

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Galena
9.8 out of 10, Exceptional, (22)
"Beautiful property overlooking the Sassafras river. Home and property above and beyond pictures. Renter easy to work with and accommodating "
United States
will u.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Be persuaded to experience this vintage cottage by the Sassa

Galena
9.2 out of 10, Wonderful, (11)
"We had a nice stay! The house had everything we needed and was comfortable for our trip. Overall the place was in good shape and worked well for us."
United States
Kristen P.
Be persuaded to experience this vintage cottage by the Sassa

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (177)
"Absolutely love this property! This is my family’s second stay here, we will definitely be coming back. Great hosts, clean house, wonderful location!"
United States
Katie H.
Chesapeake Bay House with Dock & Private Beach

Beachfront Sunsets on the Water at Oakwood Beach

Salem
10.0 out of 10, Exceptional, (43)
"House was well maintained and very clean. Fantastic view."
United States
Paul P.
Beachfront Sunsets on the Water at Oakwood Beach

Charming 3-bedroom Ranch in delightful Dover with AC

Dover
Charming 3-bedroom Ranch in delightful Dover with AC

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
United States
Ashlee S.
The price is AU$930
includes taxes & fees
13 Nov - 14 Nov
5-bedroom vacation home 5 minutes from historic Charlestown

Waterfront house with amazing views. Top of the Chesapeake

Perryville
10.0 out of 10, Exceptional, (102)
"Great accommodation overall - would visit again! Calm, great view, perfect spot for a private getaway."
United States
Jörg
Waterfront house with amazing views. Top of the Chesapeake

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

Elkton
9.6 out of 10, Exceptional, (12)
"Good experience"
United States
Thomas Z.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (58)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Perryville
9.2 out of 10, Wonderful, (181)
"Perfect spot for a relaxing weekend on the water, even if the kids are playing in a sports tournament."
United States
Donald R.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

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

Chestertown
10.0 out of 10, Exceptional, (10)
"Check-in was very easy. House was clean and well supplied with everything we needed. Peaceful and quiet. Mowed and cleared trails to enjoy. "
United States
Carol B.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown
10.0 out of 10, Exceptional, (2)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (17)
"Perfect little place for 2. Quiet Very close to Schaefers. "
United States
Karen H.
The price is AU$431
includes taxes & fees
13 Nov - 14 Nov
Historic Chesapeake City Stay

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.0 out of 10, Very good, (5)
The price is AU$1,285
includes taxes & fees
16 Nov - 17 Nov
Luxury Waterfront Home Built for Entertaining!

Tiny Home Tranquil Oasis

Bear
The price is AU$374
includes taxes & fees
15 Nov - 16 Nov
Tiny Home Tranquil Oasis

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Elkton
9.8 out of 10, Exceptional, (42)
"We stayed for my Birthday! It was definitely a great place to stay. The house was decorated beyond my expectation. We are planing to book again for Girls Weekend."
United States
Billie W.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
The price is AU$246
includes taxes & fees
17 Nov - 18 Nov
First Floor Studio Apartment in Historic Chestertown

A cottage on the shore of the Delaware River

Salem
9.8 out of 10, Exceptional, (68)
"This small home was perfect for a stay on our road trip. Beautiful views and quiet place to stay."
United States
Taylor A.
A cottage on the shore of the Delaware River

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
United States
Ann P.
Stunning waterfront villa with indoor pool and kids swing set and play area.
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

Find out more about Galena

Everything you need to know about Galena holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Galena holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Galena holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Galena holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Galena holiday rentals we have selected for you start as low as AU$246 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Galena rentals

At Expedia, we put the best Galena holiday 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 holiday.

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. 

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?

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.: This highly rated holiday home rental in Galena is located on a river, and has a patio, a BBQ and air conditioning 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 that you can cook with friends or family.

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.