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Galena Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Galena vacation rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $95
CA $163 total
includes taxes & fees
Nov 2 - Nov 3
Guest Suite for up to 2 in a Victorian on the Chester River
Restaurant

2. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is CA $781
CA $828 total
includes taxes & fees
Nov 2 - Nov 3
Bohemia Manor Farm
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (132 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $138
CA $210 total
includes taxes & fees
Nov 2 - Nov 3
First Floor Studio Apartment in Historic Chestertown
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

4. 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.
The price is CA $243
CA $287 total
includes taxes & fees
Nov 9 - Nov 10
Beachcomber Suite
A garden path leading to a wooden building with a rustic appearance.

5. 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.
The price is CA $257
CA $384 total
includes taxes & fees
Nov 3 - Nov 4
Secluded Cottage in Middle of Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $314
CA $470 total
includes taxes & fees
Nov 2 - Nov 3
Newly restored apartment in the heart of Chestertown
A living room with a sofa, a coffee table, and a patterned rug. There is a window with curtains, a door, and a small table with chairs.

7. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is CA $189
CA $419 total
includes taxes & fees
Nov 1 - Nov 2
Historic Chesapeake City Stay
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

8. Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $226
CA $266 total
includes taxes & fees
Nov 2 - Nov 3
Turtle Cove Room
A covered porch with a wooden bench, potted plants, and a decorative railing.

9. 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.
The price is CA $426
CA $638 total
includes taxes & fees
Nov 2 - Nov 3
Wren Retweet- Country Estate in Center of C’Town
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is CA $277
CA $401 total
includes taxes & fees
Nov 6 - Nov 7
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A wooden deck with outdoor furniture, a small shed, and a view of a body of water.

11. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is CA $201
CA $393 total
includes taxes & fees
Nov 3 - Nov 4
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A house with a paved walkway leading to the front door, surrounded by a landscaped garden with mulch and plants.

12. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is CA $98
CA $144 total
includes taxes & fees
Nov 9 - Nov 10
Country Get Away Studio Apartment
A boat interior with a white leather sofa, a cushioned bench, a television, and a view of the outside.

13. 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
9.8 out of 10, Exceptional, (7 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.
The price is CA $349
CA $396 total
includes taxes & fees
Nov 4 - Nov 5
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
A room with a large sliding glass door leading to a balcony with a view of the sea and a wooden deck.

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

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is CA $400
CA $613 total
includes taxes & fees
Nov 4 - Nov 5
Long Beach Cottage, (romantic couple’s getaway)
A wooden deck with lounge chairs and a dock extending into calm water.

15. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is CA $371
CA $721 total
includes taxes & fees
Nov 4 - Nov 5
Waterfront house with amazing views. Top of the Chesapeake
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is CA $102
CA $126 total
includes taxes & fees
Nov 2 - Nov 3
Charming 2-bedroom house in Aberdeen with WiFi and AC
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

17. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is CA $175
CA $203 total
includes taxes & fees
Nov 2 - Nov 3
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A spacious room with a large sliding glass door leading to a deck, a dining area with a white table, and a cozy seating area with a view of the water.

18. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is CA $333
CA $552 total
includes taxes & fees
Nov 2 - Nov 3
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

19. 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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $119
CA $198 total
includes taxes & fees
Nov 4 - Nov 5
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A covered deck area with a grill and outdoor seating.

20. 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
The price is CA $264
CA $311 total
includes taxes & fees
Nov 1 - Nov 2
Nature's Haven Tiny Home
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

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

8/10 Good
"O"
Louis 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Galena vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Galena vacation rentals we have selected for you start as low as CA $144 per night. Entering your travel dates in the search wizard 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?

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. 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.