Galena Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Galena holiday rentals

A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

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, (33 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$172
includes taxes & fees
18 Nov - 19 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
An aerial view of a property with a large house surrounded by lush greenery, a driveway, and a road nearby.

2. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is AU$282
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove Room
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, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$221
includes taxes & fees
23 Nov - 24 Nov
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 AU$303
includes taxes & fees
23 Nov - 24 Nov
Beachcomber Suite
A riverside dock with boats, a covered seating area, and a bridge in the background.

5. 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 AU$427
includes taxes & fees
24 Nov - 25 Nov
Historic Chesapeake City Stay
A wooden deck with a glass-top table and metal chairs.

6. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (53 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is AU$152
includes taxes & fees
23 Nov - 24 Nov
Country Get Away Studio Apartment
A wooden deck with two cushioned chairs, a view of a lake, and a small shed in the background.

7. 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 AU$477
includes taxes & fees
16 Nov - 17 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

8. 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 AU$404
includes taxes & fees
19 Nov - 20 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

9. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
10.0 out of 10, Exceptional, (1 review)
"I was the first guest to stay at the Bohemia Hideaway and I was impressed. The place was spotless and brand new and beautifully decorated. The Owner left a care package filled with toiletries for personal use and every coffee flavor and tea flavor you could imagine. Even little honey packets. The scenery was beautiful. Tucked away and peaceful. Thank you for a wonderful stay."
United States
Isabelle M.
The price is AU$322
includes taxes & fees
26 Nov - 27 Nov
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
A spacious living area with a dining table, sofa, and a kitchen in the background.

10. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (35 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 AU$483
includes taxes & fees
15 Nov - 16 Nov
Newly restored apartment in the heart of Chestertown
Beach bar

11. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$501
includes taxes & fees
15 Nov - 16 Nov
Bohemia Manor Farm
A wooden deck with wicker lounge chairs and a white sofa, overlooking a body of water.

12. 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 AU$617
includes taxes & fees
17 Nov - 18 Nov
Long Beach Cottage, (romantic couple’s getaway)
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

13. 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 AU$222
includes taxes & fees
2 Dec - 3 Dec
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A kitchen with white cabinets, a wooden island, and a washing machine.

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

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.2 out of 10, Good, (20 reviews)
"Nice place"
United States
christine
The price is AU$142
includes taxes & fees
15 Nov - 16 Nov
Charming 2-bedroom house in Aberdeen with WiFi and AC
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

15. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AU$694
includes taxes & fees
19 Nov - 20 Nov
5-bedroom vacation home 5 minutes from historic Charlestown
A wooden deck with lounge chairs and a dock extending into calm water.

16. 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, (116 reviews)
"Host was very communicative."
United States
Lee Anne K.
The price is AU$726
includes taxes & fees
16 Nov - 17 Nov
Waterfront house with amazing views. Top of the Chesapeake
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, (13 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 AU$202
includes taxes & fees
16 Nov - 17 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A beachside seating area with wicker chairs, a striped cushion, a wooden table, and a beach umbrella.

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, (6 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 AU$590
includes taxes & fees
17 Nov - 18 Nov
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
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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Find out more about Galena

Everything you need to know about Galena holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Galena holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Galena holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Galena holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Galena holiday rentals we have selected for you start as low as AU$501 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Galena rentals

At Expedia, we put the best Galena holiday 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 holiday.

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 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?

Sailor's Sunrise Cottage - Chesapeake Bay: This holiday home rental outside of Galena is located on a lake, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

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 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 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.