Galena Holiday Rentals

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Holiday Rentals in Galena

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, 20 reviews
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Historic Chesapeake City Stay
8.0 out of 10, Very good, 1 review
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is NZ$392
includes taxes & fees
16 Jun - 17 Jun
Historic Chesapeake City Stay
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Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, 11 reviews
"Great"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, 89 reviews
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
The price is NZ$1,180
includes taxes & fees
17 Jun - 18 Jun
Waterfront house with amazing views. Top of the Chesapeake
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, 13 reviews
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, 14 reviews
"Great location "
Family-Friendly Cottage, Walk to the Beach!
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, 60 reviews
"It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful."
The price is NZ$267
includes taxes & fees
20 Jun - 21 Jun
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.6 out of 10, Exceptional, 4 reviews
"Tv channels were sparse"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, 5 reviews
"Lovely home and hostess! Very clean and responsive. Beautiful water views. Excellent vacation home"
Chesapeake City Overlook: Breathtaking View!
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
10.0 out of 10, Exceptional, 2 reviews
"Couldn’t have asked for a better place for us. Lots of room and quiet neighborhood."
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, 19 reviews
"The location was great for us because it was relatively close to Newark, DE and Philadelphia. Water views were great from so much of the house and owners had thought of every possible touch to make people feel at home. There were plenty of outlets, chargers, TVs, tables & chairs, hooks in bathrooms, nightlights, etc. The fridge was free of all sorts of open condiments that are probably supposed to be helpful for guests but that drive my husband crazy as they've taken up half the fridge in the...
Beachfront Sunsets on the Water at Oakwood Beach
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, 36 reviews
"House was very clean and in an excellent location. However the grounds were in need of weeding to the point that the advertised upper bay view was blocked or partially blocked from many areas. Host was prompt in responding when I reached out."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, 80 reviews
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, 126 reviews
"This house setting was a little slice of paradise. We saw a beaver swimming, blue herons, eagles, ducks in the water and yard. Would definitely come back again."
The price is NZ$1,051
includes taxes & fees
17 Jun - 18 Jun
Top of the Chesapeake - Minutes from Historic Charlestown
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, 28 reviews
"Pretty house with plenty of room. Easy check in and out."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, 155 reviews
"This River property is a little bit of Paradise away from home! It is everything and more as advertised! My husband and I leased the property for 5 nights for a family reunion, ages 1 to 89 years old! My family of 5, my Mom, Dad and Grandmother, my brothers family of 4 and my nieces family of 3. The house was big enough for all of us to be together or everyone could have their own space. We enjoyed the pool, the hot tub, the playground and the sunsets across the river were amazing. My...
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
9.6 out of 10, Exceptional, 44 reviews
"Owner very helpful to anything we needed. Was within walking distance to everything in town which has wonderful shops and places to eat."
Cozy home with fenced in yard-Pet Friendly. 2 block walk to historic downtown!
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, 22 reviews
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, 7 reviews
"Way to make us feel welcome. From the accommodations to the amenities this property is a vrbo treasure. The owners exceeded our expectations in every way."
Historic home in the heart of Main Street- walkable to shops and restaurants
Don't see what you're looking for?
See all available properties in Galena
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.

Other types of properties in Galena you may be interested in

Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, 1,388 reviews
"I liked the Price."
The price is NZ$152
includes taxes & fees
1 Jul - 2 Jul
Bally's Dover Casino Resort
Red Roof Inn & Suites Newark - University
2.0 star property
5.8 out of 10, 1,009 reviews
"Check-in started off rocky as I had just driven 7 hours and was given a different type of room than I had booked. However, the balcony (and luckily great weather) made up for that. Yes, it is a beaten-up old motor hotel, but it was terrific overall. Dogs welcome, quiet (except for intermittent morons with loud cars on S College), felt safe, cute coffee maker, and the BED WAS FANTASTIC!"
The price is NZ$142
includes taxes & fees
24 Jun - 25 Jun
Red Roof Inn & Suites Newark - University
Microtel Inn & Suites by Wyndham Dover
2.0 star property
8.0 out of 10, Very good, 1,001 reviews
"Very clean, nice room, nice staff. Nice breakfast "
The price is NZ$159
includes taxes & fees
17 Jun - 18 Jun
Microtel Inn & Suites by Wyndham Dover
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Galena holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Galena. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Galena. Seeing all the best attractions is bound to make you fall in love with Galena. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Galena short-term rentals, that won’t be hard to do.

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?

Waterfront house with amazing views. Top of the Chesapeake: This holiday home rental outside of Galena is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Havre de Grace Maritime Museum, or get out into nature at a spot like Betterton Beach. In the wider area, you’ll find Bohemia Vista Marina and Elk Neck State Park.

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.

Recent reviews of Galena properties
Expedia verified reviews