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Callaway Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Callaway holiday rentals

A two-story house with a balcony, surrounded by trees and a wooden fence.

1. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (6 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 HK$2,689
HK$6,257 total
includes taxes & fees
30 Aug - 31 Aug
Charming Waterfront 3-bedroom house in Piney Point
A single-story house with a front porch, a small deck, and a number '4' on the side.

2. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$1,514
HK$2,372 total
includes taxes & fees
27 Aug - 28 Aug
Coles Point Marina
A spacious living room with a large sofa, a television, and a view of the ocean.

3. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$2,353
HK$5,538 total
includes taxes & fees
8 Sept - 9 Sept
4-BR Waterfront Turret Home
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

4. 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 HK$1,873
HK$4,620 total
includes taxes & fees
23 Aug - 24 Aug
Anne & Fred`s Leonardtown Home W/ Arcade room!
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

5. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (53 reviews)
"My husband and I had a great 3 day getaway here. The view was spectacular! The convenience from walking to the dock to the house was awesome! The only “bad” thing I would say is the water….it has an awful sulfur smell that is very strong. Overall, we loved our stay & would stay here again!"
United States
Ashley D.
The price is HK$1,372
HK$2,687 total
includes taxes & fees
23 Aug - 24 Aug
Cozy Virginia Potomac Riverfront Cottage
A covered patio with a view of a lake, furnished with chairs and a table.

6. 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, (13 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is HK$1,372
HK$3,025 total
includes taxes & fees
14 Sept - 15 Sept
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A room with a wooden bench, a small table, and a view of the outdoors.

7. Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
10.0 out of 10, Exceptional, (1 review)
"We were going to an evening event at Stratford Hall (about 25 min away). There is so much history in the area. Beautiful spot on the river. The screened in porch was the bomb! Huge. So relaxing. Well stocked. Easy check out. Do pay attention to room configuration. The bedroom with twins was a loft like area but had the nicer bathroom. We used the kayaks. Had everything we needed. Host communication was great despite Vrbo platform was a challenge."
United States
Paige
The price is HK$2,078
HK$3,950 total
includes taxes & fees
15 Sept - 16 Sept
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

8. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (57 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is HK$1,231
HK$2,535 total
includes taxes & fees
15 Sept - 16 Sept
Soul Oasis - home on the Chesapeake Bay
A spacious cabin with a wooden interior, a fireplace, a television, and a dining area.

9. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is HK$4,007
HK$8,972 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
A spacious cabin with a wooden interior, a fireplace, a television, and a dining area.

10. 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 HK$3,395
HK$9,014 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
A pathway lined with trees and lights leading to a wooden building with a visible window.

11. 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, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is HK$3,622
HK$6,765 total
includes taxes & fees
26 Aug - 27 Aug
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

12. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is HK$3,624
HK$7,767 total
includes taxes & fees
17 Sept - 18 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A sunlit room with a sofa, a wooden table, and a dining area.

13. Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (138 reviews)
"The property was very clean and well-stocked. Beds were comfortable and pictures matched reality. Jocelyn was so kind to leave us ingredients for smores and Easter eggs for my kids to have a hunt in the backyard. Overall, we had a wonderful stay and hope to make it back again some time!"
United States
Allie P.
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (17 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is HK$1,355
HK$2,949 total
includes taxes & fees
21 Aug - 22 Aug
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

15. Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (39 reviews)
"What a lovely weekend. Beautiful views, winery at Ingleside , breakfast and shopping in Warsaw, grilling and paddle boating. Thank you. It was just what we needed!!’"
United States
Diana H.
The price is HK$2,407
HK$4,752 total
includes taxes & fees
15 Sept - 16 Sept
Waterfront Reset: Views, Games, Boats & Total Calm
A house with a large lawn and a dock extending into a calm lake.

16. 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 HK$2,117
HK$2,551 total
includes taxes & fees
23 Aug - 24 Aug
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A house with a large lawn and a dock extending into a calm lake.

17. 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 HK$2,117
HK$2,551 total
includes taxes & fees
23 Aug - 24 Aug
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

18. 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, (16 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 HK$1,960
HK$4,632 total
includes taxes & fees
9 Sept - 10 Sept
Riverfront Home w/Dock · Fire Pit · Kids Play Area
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

19. 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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$1,044
HK$2,162 total
includes taxes & fees
31 Aug - 1 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
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

Sleep Inn & Suites California MD

Sleep Inn & Suites California MD

8/10 Good
"Very clean and helpful staff."
Laurie 1-night trip
Posted 2 hours ago
Sleep Inn & Suites California MD

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?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This holiday home rental outside of Callaway is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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 Patuxent River Naval Air Station and Dennis Point Marina.

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.