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Galena Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Galena vacation rentals

Exterior

1. 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
9.8 out of 10, Exceptional, (24 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
$118 nightly
The price is $125
Aug 10 - Aug 11
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Marina

2. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (26 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
$266 nightly
The price is $282
Aug 9 - Aug 10
Total with taxes and fees
Historic Chesapeake City Stay
Exterior

3. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (45 reviews)
"Perfect in every way… a great stay"
United States
Robert B.
$105 nightly
The price is $111
Aug 17 - Aug 18
Total with taxes and fees
Country Get Away Studio Apartment
Property grounds

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
$144 nightly
The price is $159
Aug 10 - Aug 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
1 bedroom, WiFi, bed sheets

5. Turtle Cove Room

Turtle Cove Room
Kent County
$160 nightly
The price is $174
Aug 10 - Aug 11
Total with taxes and fees
Turtle Cove Room
Property grounds

6. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$181 nightly
The price is $196
Aug 24 - Aug 25
Total with taxes and fees
Beachcomber Suite
Interior

7. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
9.8 out of 10, Exceptional, (10 reviews)
"The pictures were accurate. Our host communicated with us in a timely manner. Everything was as it said it was going to be everything in the house worked and made sense. We really enjoyed our stay. We definitely will be staying at this location again when we come in into Dover."
United States
Laura
$159 nightly
The price is $163
Sep 6 - Sep 7
Total with taxes and fees
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
TV

8. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.4 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
$91 nightly
The price is $97
Aug 25 - Aug 26
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
TV, fireplace

9. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
$271 nightly
The price is $281
Aug 19 - Aug 20
Total with taxes and fees
Secluded Cottage in Middle of Chestertown
Interior

10. Cozy Room in Dover

Cozy Room in Dover
Dover
$94 nightly
The price is $96
Aug 12 - Aug 13
Total with taxes and fees
Cozy Room in Dover
Beach nearby

11. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$343 nightly
The price is $379
Aug 30 - Aug 31
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Terrace/patio

12. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
$224 nightly
The price is $233
Aug 9 - Aug 10
Total with taxes and fees
Nature's Haven Tiny Home
Terrace/patio

13. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
$228 nightly
The price is $237
Aug 9 - Aug 10
Total with taxes and fees
Tiny Home Tranquil Oasis
Smart TV, books

14. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
$319 nightly
The price is $352
Aug 20 - Aug 21
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
Interior

15. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
$286 nightly
The price is $297
Aug 10 - Aug 11
Total with taxes and fees
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Smart TV

16. Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (12 reviews)
"Very cool place, walking distance to everything."
United States
Brett S.
$245 nightly
The price is $259
Sep 7 - Sep 8
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Property grounds

17. Sunset River Shack -amazing waterfront view

Sunset River Shack -amazing waterfront view
Elkton
9.6 out of 10, Exceptional, (9 reviews)
"The home is nice The view from the deck was wonderful But there wasn’t access to the water Easy to find and we really enjoyed the area"
United States
Hope D.
$417 nightly
The price is $441
Aug 9 - Aug 10
Total with taxes and fees
Sunset River Shack -amazing waterfront view
Pool

18. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
$217 nightly
The price is $223
Sep 6 - Sep 7
Total with taxes and fees
Mini Aruba RV/Glamping Tent
Property grounds

19. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
$517 nightly
The price is $539
Sep 2 - Sep 3
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town
Sun loungers, beach towels

20. 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, (156 reviews)
"Kitchen was fully equipped for a large family, beautiful views and perfect family getaway! "
United States
Kshama C.
$555 nightly
The price is $588
Sep 8 - Sep 9
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
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

Comfort Inn & Suites North East

Comfort Inn & Suites North East

10/10 Excellent
"Clean, quiet and right next to fast food and across the street from convenience store and gas station."
Laura A 1-night trip
Posted 5 hours ago
Comfort Inn & Suites North East

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.

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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This vacation home rental near Galena is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 hot tub.

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. Sassafras Harbor Marina and Galena Town Hall 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.