Galesville Holiday Rentals

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Our top choices for Galesville holiday rentals

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is NZ$425
includes taxes & fees
25 Mar - 26 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!

Waterfront Unit | Dock, Kayaks & SUPs Included

Waterfront Unit | Dock, Kayaks & SUPs Included
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
The price is NZ$541
includes taxes & fees
25 Mar - 26 Mar
Waterfront Unit | Dock, Kayaks & SUPs Included

Lower Level Loft - Adorable Studio Apt. Near BWI

Lower Level Loft - Adorable Studio Apt. Near BWI
South Gate
9.4 out of 10, Exceptional, (14 reviews)
"No complaints"
United States
Shelby B.
The price is NZ$184
includes taxes & fees
30 Mar - 31 Mar
Lower Level Loft - Adorable Studio Apt. Near BWI

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (3 reviews)
"Nice location tucked away in a quiet neighborhood. Pet friendly with some small grass areas around the house. Convenient 2-car parking area. Great neighborhood for walking with the dogs.Perfect spot for a couple or a small family. Quick drive to some great restaurants, downtown Annapolis, or the Naval Academy. "
United States
Chad B.
The price is NZ$373
includes taxes & fees
2 Apr - 3 Apr
Cute, Cozy 2-bedroom house in near Annapolis with water access

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is NZ$636
includes taxes & fees
5 Apr - 6 Apr
Walk to Beach! King Bed & Free Beach Passes

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is NZ$551
includes taxes & fees
25 Mar - 26 Mar
Large 2 bedroom house with private parking in a nice neighborhood

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$743
includes taxes & fees
25 Mar - 26 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$768
includes taxes & fees
25 Mar - 26 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

The Understory | Cozy Capitol Heights Suite

The Understory | Cozy Capitol Heights Suite
Seat Pleasant
The price is NZ$548
includes taxes & fees
31 Mar - 1 Apr
The Understory | Cozy Capitol Heights Suite

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is NZ$566
includes taxes & fees
12 Apr - 13 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.0 out of 10, Wonderful, (4 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is NZ$780
includes taxes & fees
25 Mar - 26 Mar
Renovated Bungalow | Walk to Beach | Dog-Friendly

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is NZ$729
includes taxes & fees
26 Mar - 27 Mar
40' Bristol sailboat with spectacular views

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is NZ$776
includes taxes & fees
15 Apr - 16 Apr
Sunset Cottage - West River Access and Views!

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.
Edgewater
The price is NZ$5,139
includes taxes & fees
25 Mar - 26 Mar
Luxurious 50 ft. Fountaine Pajot Saba. Six Cabin six head layout.

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
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 NZ$653
includes taxes & fees
29 Mar - 30 Mar
Pool Loft Suite | Bay Access & Beach Passes

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is NZ$557
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (12 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is NZ$980
includes taxes & fees
25 Mar - 26 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$690
includes taxes & fees
25 Mar - 26 Mar
Waterfront Oasis of Annapolis Star

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$915
includes taxes & fees
25 Mar - 26 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
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

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 favorite 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 depends 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 NZ$425 per night. Entering your travel dates in the search wizard you might find 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?

Charming Annapolis WaterVIEW Home: This holiday home rental outside of Galesville is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 Triton Beach. 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.