Callaway Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

This weekend
Next weekend

Our top choices for Callaway holiday rentals

9.8 out of 10, Exceptional, (40)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is HK$973
HK$2,113 total
includes taxes & fees
11 Jan - 12 Jan
Soul Oasis - home on the Chesapeake Bay
9.4 out of 10, Exceptional, (10)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is HK$1,002
HK$2,457 total
includes taxes & fees
11 Jan - 12 Jan
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
10.0 out of 10, Exceptional, (11)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
The price is HK$1,168
HK$2,122 total
includes taxes & fees
13 Jan - 14 Jan
Waterfront home where you can relax or enjoy the things the Northern Neck.

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is HK$2,067
HK$2,472 total
includes taxes & fees
16 Jan - 17 Jan
Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (5)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
The price is HK$1,296
HK$3,172 total
includes taxes & fees
13 Jan - 14 Jan
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Holiday Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is HK$1,028
HK$3,329 total
includes taxes & fees
21 Jan - 22 Jan
Luxury Modern Waterfront Retreat
10.0 out of 10, Exceptional, (30)
"Great spot"
United States
SHAWN W.
The price is HK$1,557
HK$3,593 total
includes taxes & fees
11 Jan - 12 Jan
MLK Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
10.0 out of 10, Exceptional, (11)
"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 HK$2,102
HK$2,550 total
includes taxes & fees
13 Jan - 14 Jan
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
10.0 out of 10, Exceptional, (5)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is HK$1,099
HK$2,618 total
includes taxes & fees
9 Feb - 10 Feb
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
2.0 star property
The price is HK$934
HK$2,022 total
includes taxes & fees
10 Jan - 11 Jan
Back Creek Villa Open Deck Solomons Island Maryland

Cabin in Hague

Coles Point Marina
2.0 star property
The price is HK$2,073
HK$2,918 total
includes taxes & fees
17 Jan - 18 Jan
Coles Point Marina

Holiday Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is HK$1,082
HK$3,052 total
includes taxes & fees
19 Jan - 20 Jan
Potomac Vista Cottage
3.0 star property
The price is HK$2,850
HK$6,520 total
includes taxes & fees
19 Jan - 20 Jan
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Holiday Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$2,725
HK$5,573 total
includes taxes & fees
11 Jan - 12 Jan
4-BR Waterfront Turret Home
10.0 out of 10, Exceptional, (1)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is HK$2,569
HK$6,804 total
includes taxes & fees
14 Jan - 15 Jan
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is HK$2,336
HK$4,462 total
includes taxes & fees
10 Jan - 11 Jan
Charming Waterfront 3-bedroom house in Piney Point
9.2 out of 10, Wonderful, (5)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
The price is HK$1,947
HK$4,510 total
includes taxes & fees
12 Jan - 13 Jan
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Mechanicsville

Come relax yourself a while
The price is HK$1,927
HK$4,570 total
includes taxes & fees
10 Jan - 11 Jan
Come relax yourself a while
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 Callaway Hotel Reviews

Find out more about Callaway

Search for holiday rentals in Callaway on Expedia! You can easily find your home rentals, villas, holiday apartments in Callaway using one of the methods below:

  • View our selection of featured holiday rentals in Callaway
  • Use the map to find apartments and other holiday homes in the Callaway neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Callaway while they last

Look no further and take a look at our great range of rental properties in Callaway!

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?

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp: This holiday home rental outside of Callaway is located on the beach, and has a balcony, a garden 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.

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 Cecil's Old Mill and Patuxent River Naval Air Museum.

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.