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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 ￥10,721
￥19,720 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 ￥63,693
￥67,515 total
includes taxes & fees
Oct 31 - Nov 1
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 ￥15,608
￥25,042 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 ￥27,433
￥33,746 total
includes taxes & fees
Nov 9 - Nov 10
Beachcomber Suite
A garden with a wooden bridge, lush greenery, and a variety of plants.

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 ￥28,946
￥43,362 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 ￥35,474
￥55,686 total
includes taxes & fees
Nov 2 - Nov 3
Newly restored apartment in the heart of Chestertown
A riverside dock with boats, a covered seating area, and a bridge in the background.

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 ￥21,284
￥49,133 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 ￥25,541
￥31,683 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 ￥48,017
￥72,033 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 ￥31,217
￥45,123 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 ￥22,703
￥45,958 total
includes taxes & fees
Nov 1 - Nov 2
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A wooden cabin with a porch, surrounded by dense forest.

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 ￥11,036
￥17,547 total
includes taxes & fees
Nov 10 - Nov 11
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)
"The host was great and easy to communicate with. It was a first time experience staying on a boat for my family and I and we really enjoyed it. Perfect for a few nights to visit family nearby."
United States
Jessica
The price is ￥39,415
￥46,864 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥45,122
￥71,951 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 ￥46,510
￥85,733 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 ￥11,777
￥15,826 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥19,708
￥24,233 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 ￥37,602
￥64,721 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 ￥14,978
￥25,112 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥29,798
￥36,815 total
includes taxes & fees
Oct 31 - Nov 1
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

Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Dover near Speedway

10/10 Excellent
"This is our prefered hotel due to it looks clean. I had everything I needed in the room. The bed was confortable, and it is close to everything in the area."
Gladys 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Dover near Speedway

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 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.