Galesville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Galesville holiday rentals

10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$580
includes taxes & fees
29 Jan - 30 Jan
Waterfront Oasis of Annapolis Star
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is AU$374
includes taxes & fees
29 Jan - 30 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$354
includes taxes & fees
28 Jan - 29 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AU$1,012
includes taxes & fees
28 Jan - 29 Jan
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AU$750
includes taxes & fees
28 Jan - 29 Jan
Cute bungalow blocks to Stadium
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
The price is AU$468
includes taxes & fees
28 Jan - 29 Jan
2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AU$550
includes taxes & fees
28 Jan - 29 Jan
Luxury Pool Loft sleeps 4

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (74 reviews)
"Great location!"
United States
Burton S.
The price is AU$519
includes taxes & fees
9 Feb - 10 Feb
Cozy 2br home w/ parking in downtown Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$682
includes taxes & fees
29 Jan - 30 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (18 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is AU$447
includes taxes & fees
28 Jan - 29 Jan
Walk to Beach! King Bed & Free Beach Passes
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is AU$550
includes taxes & fees
29 Jan - 30 Jan
Walk to the stadium! - Lighthouse on Glenwood
9.4 out of 10, Exceptional, (36 reviews)
"Just as advertised. Clean and quiet."
United States
Robert B.
The price is AU$445
includes taxes & fees
29 Jan - 30 Jan
Large 2 bedroom house with private parking in a nice neighborhood
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$705
includes taxes & fees
3 Feb - 4 Feb
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is AU$673
includes taxes & fees
9 Feb - 10 Feb
Upscale Condo in Annapolis

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is AU$683
includes taxes & fees
29 Jan - 30 Jan
Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$730
includes taxes & fees
29 Jan - 30 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (2 reviews)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
The price is AU$1,215
includes taxes & fees
28 Jan - 29 Jan
Stunning 4 BR Home - Walking Distance to Stadium
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is AU$612
includes taxes & fees
28 Jan - 29 Jan
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Holiday Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Great house, perfect for Navy football game"
United States
Kathy N.
The price is AU$1,137
includes taxes & fees
28 Jan - 29 Jan
All Star Annapolis Retreat - Walk to Stadium

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is AU$809
includes taxes & fees
28 Jan - 29 Jan
Secluded Cozy Cottage in Historic Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Galesville Hotel Reviews

Find out more about Galesville

Everything you need to know about Galesville 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 Galesville 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 Galesville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Galesville holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Galesville. 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 Galesville 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 Galesville holiday rentals we have selected for you start as low as AU$1,800 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Galesville rentals

At Expedia, we put the best Galesville 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 Galesville 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 Galesville 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 Galesville. 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

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 Maryland Quiet Waters Park. In the wider area, you’ll find London Town and Kunta Kinte–Alex Haley Memorial.

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.