Galena Vacation Rentals from ￥24,821: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Galena?

Sailor's Sunrise Cottage - Chesapeake Bay : This vacation home rental near Galena is located on a lake and has a fireplace, 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 fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

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Our top choices for Galena vacation rentals

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

Millington

Riley B.

￥19,545 total

includes taxes & fees

Sep 10 - Sep 11

Luxury House, Multiple Bedrooms, Lake View

2. Bohemia Manor Farm

Chesapeake City

￥57,922 total

includes taxes & fees

Sep 8 - Sep 9

3. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveler

￥55,192 total

includes taxes & fees

Sep 8 - Sep 9

4. Historic Chesapeake City Stay

Chesapeake City

Martha J.

￥43,562 total

includes taxes & fees

Sep 8 - Sep 9

5. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

￥24,821 total

includes taxes & fees

Sep 8 - Sep 9

6. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

Chesapeake City

Deb D.

￥44,887 total

includes taxes & fees

Sep 30 - Oct 1

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

Bear

Justin M.

￥46,448 total

includes taxes & fees

Sep 9 - Sep 10

8. Long Beach Cottage, (romantic couple’s getaway)

Charlestown

Mike F.

￥96,191 total

includes taxes & fees

Sep 22 - Sep 23

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

Chestertown

Mandy D.

￥75,204 total

includes taxes & fees

Sep 8 - Sep 9

10. Nature's Haven Tiny Home

Bear

Maxwell

￥36,801 total

includes taxes & fees

Sep 8 - Sep 9

11. Beachcomber Suite

Kent County

"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...

Lisa E.

￥30,645 total

includes taxes & fees

Sep 14 - Sep 15

12. 5-bedroom vacation home 5 minutes from historic Charlestown

Perryville

Teresa M.

￥84,226 total

includes taxes & fees

Sep 8 - Sep 9

13. Tiny Home Tranquil Oasis

Bear

Erin C.

￥37,582 total

includes taxes & fees

Sep 8 - Sep 9

14. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

￥43,971 total

includes taxes & fees

Sep 8 - Sep 9

15. Elegant Family Stay • Quiet Neighborhood • Comfort

New Castle

Daniel J.

￥58,162 total

includes taxes & fees

Sep 8 - Sep 9

16. Turtle Cove Room

Kent County

￥27,225 total

includes taxes & fees

Sep 14 - Sep 15

17. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

￥49,326 total

includes taxes & fees

Oct 4 - Oct 5

18. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Hartly

￥23,852 total

includes taxes & fees

Sep 13 - Sep 14

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

Aberdeen

christine

￥17,474 total

includes taxes & fees

Sep 13 - Sep 14

20. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

￥44,721 total

includes taxes & fees

Oct 5 - Oct 6

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Top Galena Hotel Reviews

Great Wolf Lodge Perryville

8/10 Good

"VERY pricey. But, all in all, our family of 15 had a blast!"

Holiday Inn Express Hotel & Suites Dover by IHG

10/10 Excellent

"My daughter and I had a great stay everything was clean the breakfast was tasty the room was clean and very spacious but the bed and pillows was so comfy i wish I could take it home with me staff was so friendly even the cleaning ladies was so nice we had a great time"

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent

"Five-Star Stay! My wife and I had an outstanding stay at La Quinta Inn in Aberdeen, Maryland. The room was absolutely spotless, and the property appeared to have been recently renovated—it felt fresh and almost brand new. When we checked in Friday, September 4, at approximately 8 PM, the young gentleman at the front desk was exceptionally helpful, professional, and welcoming. We were so impressed that we asked his age, and he told us he was 21. Unfortunately, I don’t remember his name, but I hope management can identify him from the date and time and recognize him for his excellent customer service. He represented the hotel extremely well. The next morning at breakfast, we met a wonderful woman who was maintaining the breakfast area. Again, I apologize that I don’t remember her name, but she was incredibly gracious, friendly, and helpful. The breakfast was tasty, and the atmosphere was excellent. I also enjoyed a relaxing swim in the beautiful outdoor pool Friday evening—a perfect way to unwind after traveling. Overall, this was truly a five-star experience. The cleanliness, recent renovations, amenities, and especially the wonderful staff made our stay exceptional. We would definitely stay here again!"

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

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:

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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?

Sailor's Sunrise Cottage - Chesapeake Bay: This vacation home rental near Galena is located on a lake and has a fireplace, 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 fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 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 Frightland, 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.

Room 1

Check prices for these dates

Our top choices for Galena vacation rentals

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

2. Bohemia Manor Farm

3. Newly restored apartment in the heart of Chestertown

4. Historic Chesapeake City Stay

5. First Floor Studio Apartment in Historic Chestertown

6. HISTORIC WATERFRONT 2 Bedrooms/4 beds in Chesapeake City with AC

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

8. Long Beach Cottage, (romantic couple’s getaway)

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

10. Nature's Haven Tiny Home

11. Beachcomber Suite

12. 5-bedroom vacation home 5 minutes from historic Charlestown

13. Tiny Home Tranquil Oasis

14. Secluded Cottage in Middle of Chestertown

15. Elegant Family Stay • Quiet Neighborhood • Comfort

16. Turtle Cove Room

17. Waterfront Retreat with Private Dock and Beach

18. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

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

20. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Find vacation rentals that suit your style

Top Galena Hotel Reviews

Great Wolf Lodge Perryville

Red Roof Inn & Suites Dover Downtown

Fairfield Inn & Suites by Marriott Middletown

Red Roof Inn Perryville

Holiday Inn Express Hotel & Suites Dover by IHG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

Comfort Inn & Suites Dover near Speedway

Red Roof Inn & Suites Newark - University

The Lodge at Great Oak Landing

Find out more about Galena

Frequently asked questions