Galesville Holiday Rentals

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Holiday Rentals in Galesville

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
8.0 out of 10, Very good, (4)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (49)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"The place was inviting and beautiful. Will definitely stay there again."
The Cozy Crab- Your Charming Haven in Lovely North Beach!

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (75)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is AU$717
includes taxes & fees
30 July - 31 July
Waterfront Oasis of Annapolis Star

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$495
includes taxes & fees
11 Aug - 12 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (35)
"Such a cute and unique place to stay. Very peaceful. "
Chesapeake Houseboat Getaway on Kent Island, Maryland

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (11)
"Very clean beautiful house! We stayed there for a wedding weekend and it was perfect. Great location. The hosts were wonderful and got back to us right away! Would love to go back one day."
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (42)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."
The price is AU$844
includes taxes & fees
18 Aug - 19 Aug
Edgewater/Mayo Gateaway w/ Hot Tub

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (79)
"Excellent stay. We look forward to returning."
Romantic Two Bedroom Condo

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.2 out of 10, Wonderful, (25)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (1)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is AU$530
includes taxes & fees
30 July - 31 July
Waterfront Getaway, Dock Your Boat & Play!

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (76)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes

Large 2 bedroom house with private parking in a nice neighborhood

9.6 out of 10, Exceptional, (26)
"We stayed here for about a month while we found and bought a house. It was very comfortable, near shopping, near a dog park, and a great place to relax after work as well as make our meals and do laundry. Owners were quick to respond to questions or issues, friendly and easy to get along with."
The price is AU$585
includes taxes & fees
31 July - 1 Aug
Large 2 bedroom house with private parking in a nice neighborhood

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

10.0 out of 10, Exceptional, (39)
"Loved the location and the pristine condition of the house. "
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
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 Galesville Hotel Reviews

Frequently asked questions

Are there holiday rentals in Galesville?

Yes, there are holiday rentals close to the most popular sights in Galesville, or you can select a more secluded option if you're looking for a relaxing stay. Galesville is known for its shopping and restaurants. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Galesville has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Galesville is located in the city centre, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Galesville?

Choose from 3 Expedia holiday rentals in Galesville for a memorable holiday.

What’s there to see and do in Galesville?

Enjoy the area's cultural attractions such as Galesville Heritage Museum, or get outdoors into nature at a spot like Shadyside Park. In the wider area, you’ll find London Town and Maryland Quiet Waters Park.

What’s a holiday rental in Galesville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Galesville. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and bustling concierge 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 is another reason why a holiday rental is an attractive option for a small group gathering.