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Callaway Holiday Rentals

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Our top choices for Callaway holiday rentals

1. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is NZ$728
includes taxes & fees
20 Oct - 21 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

2. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is NZ$432
includes taxes & fees
6 Oct - 7 Oct
Coles Point Marina

3. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful location "
United States
Jonathan M.
The price is NZ$1,447
includes taxes & fees
26 Oct - 27 Oct
2 Acre Oasis with Private Beach! Family and dog friendly!

4. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,310
includes taxes & fees
6 Oct - 7 Oct
4-BR Waterfront Turret Home

5. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is NZ$1,025
includes taxes & fees
6 Oct - 7 Oct
Anne & Fred`s Leonardtown Home W/ Arcade room!

6. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is NZ$1,307
includes taxes & fees
19 Oct - 20 Oct
Charming Waterfront 3-bedroom house in Piney Point

7. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (3 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,767
includes taxes & fees
6 Oct - 7 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

8. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is NZ$816
includes taxes & fees
7 Oct - 8 Oct
Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

9. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is NZ$756
includes taxes & fees
6 Oct - 7 Oct
2 Bedroom Cottage at Coles Point Marina

10. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is NZ$1,495
includes taxes & fees
6 Oct - 7 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

11. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is NZ$2,074
includes taxes & fees
6 Oct - 7 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub

12. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is NZ$470
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

13. Waterfront Game-Themed Getaway · Dock & Kayaks

Waterfront Game-Themed Getaway · Dock & Kayaks
Montross
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
The price is NZ$853
includes taxes & fees
28 Oct - 29 Oct
Waterfront Game-Themed Getaway · Dock & Kayaks

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is NZ$2,099
includes taxes & fees
6 Oct - 7 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub

15. Riverfront Home w/Dock · Fire Pit · Kids Play Area

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (17 reviews)
"Everything about this stay was FANTASTIC. The host was amazing, the condo was in excellent condition and the view is AMAZING! Enjoyed everything about this stay!"
United States
N C.
The price is NZ$986
includes taxes & fees
6 Oct - 7 Oct
Riverfront Home w/Dock · Fire Pit · Kids Play Area

16. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is NZ$404
includes taxes & fees
9 Oct - 10 Oct
Just a getaway piece of property

17. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (19 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is NZ$791
includes taxes & fees
26 Oct - 27 Oct
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

18. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is NZ$576
includes taxes & fees
6 Oct - 7 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

19. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is NZ$529
includes taxes & fees
6 Oct - 7 Oct
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
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 Callaway Hotel Reviews

Find out more about Callaway

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 Callaway 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 Callaway. 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 Callaway. Seeing all the best attractions is bound to make you fall in love with Callaway. 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 Callaway short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Callaway?

Yes, there are holiday rentals close to the most popular sights in Callaway, or you can select a more secluded option if you're looking for a relaxing stay.

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

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This holiday home rental outside of Callaway offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Callaway?

While exploring the area, visit family-friendly sights like Michael P. O'Brien Athletics and Recreation Center, or get outside and enjoy nature at St. Mary's River State Park. In the wider area, you’ll find Patuxent River Naval Air Museum and Patuxent River Naval Air Station.

What’s a holiday rental in Callaway like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Callaway. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.