Galena Holiday Rentals

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Check prices for these dates

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Galena holiday rentals

Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$1,399
HK$2,775 total
includes taxes & fees
4 Jan - 5 Jan 2026
Amazing Modern house with a full kitchen and parking
Exterior
Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is HK$528
HK$972 total
includes taxes & fees
1 Jan - 2 Jan 2026
Guest Suite for up to 2 in a Victorian on the Chester River
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is HK$1,399
HK$2,603 total
includes taxes & fees
28 Dec - 29 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is HK$629
HK$1,919 total
includes taxes & fees
29 Dec - 30 Dec
Historic Chesapeake City Stay
Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is HK$544
HK$865 total
includes taxes & fees
15 Jan - 16 Jan 2026
Country Get Away 1 Bedroom Apartment
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Elkton
8.2 out of 10, Very good, (12)
"Nice and quiet place to stay"
United States
Gary M.
The price is HK$1,049
HK$2,134 total
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is HK$769
HK$1,234 total
includes taxes & fees
29 Dec - 30 Dec
First Floor Studio Apartment in Historic Chestertown
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug
Betterton
The price is HK$1,749
HK$3,237 total
includes taxes & fees
30 Dec - 31 Dec
Grandma’s Cottage will wrap around you like a warm hug
Fridge, microwave, oven, stovetop
Cozy loft above ink shop

Cozy loft above ink shop

Cozy loft above ink shop
Bear
9.6 out of 10, Exceptional, (5)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is HK$715
HK$903 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy loft above ink shop
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is HK$1,360
HK$2,354 total
includes taxes & fees
19 Jan - 20 Jan 2026
Waterfront Retreat with Private Dock and Beach
Outdoor spa tub
Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
United States
Elisheva K.
Long Beach Cottage, (romantic couple’s getaway)
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is HK$1,532
HK$3,461 total
includes taxes & fees
5 Jan - 6 Jan 2026
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is HK$1,346
HK$1,576 total
includes taxes & fees
7 Jan - 8 Jan 2026
High Tide Haven Suite
A heated pool
Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater
2.0 star property
Middletown
The price is HK$1,042
HK$4,256 total
includes taxes & fees
14 Jan - 15 Jan 2026
Heated Pool • Private Backyard • Home Theater
Outdoor dining
Spacious 4-bedroom house with backyard oasis

Spacious 4-bedroom house with backyard oasis

Spacious 4-bedroom house with backyard oasis
Middletown
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this gorgeous house! Very comfortable and nicely appointed."
United States
Jordan K.
The price is HK$1,806
HK$8,421 total
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 4-bedroom house with backyard oasis
Sun-loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is HK$2,511
HK$4,672 total
includes taxes & fees
29 Dec - 30 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
Private kitchen
JVA LUXURY HOUSING

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is HK$3,109
HK$4,577 total
includes taxes & fees
8 Jan - 9 Jan 2026
JVA LUXURY HOUSING
6 bedrooms, iron/ironing board, travel cot, WiFi
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.8 out of 10, Excellent, (8)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is HK$3,847
HK$6,475 total
includes taxes & fees
1 Jan - 2 Jan 2026
Luxury Waterfront Home Built for Entertaining!
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

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

10/10 Excellent
"Front desk staff. He was very nice and informative. "
Daniel 1-night trip
Posted 4 days ago
Hampton Inn & Suites Baltimore/Aberdeen

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?

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 Crumpton Auction, 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.