Default HTG hotel image

Callaway Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Callaway vacation rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (51 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is SAR 574
SAR 1,186 total
includes taxes & fees
7 Jul - 8 Jul
Soul Oasis - home on the Chesapeake Bay
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is SAR 750
SAR 1,163 total
includes taxes & fees
24 Jun - 25 Jun
Coles Point Marina
Interior

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 SAR 1,295
SAR 2,234 total
includes taxes & fees
6 Jul - 7 Jul
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Fridge, microwave, oven, stovetop

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, (15 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 SAR 875
SAR 2,124 total
includes taxes & fees
29 Jun - 30 Jun
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Sun loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"Second time here and we love the convenience to Prince Frederick and the comfort offered by the hosts. "
United States
RACHEL S.
The price is SAR 1,132
SAR 1,355 total
includes taxes & fees
22 Jun - 23 Jun
Cottage Located on the Patuxent River!
Interior

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, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is SAR 638
SAR 1,418 total
includes taxes & fees
22 Jun - 23 Jun
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is SAR 1,295
SAR 1,589 total
includes taxes & fees
22 Jun - 23 Jun
2 Bedroom Cottage at Coles Point Marina
Exterior

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 SAR 1,013
SAR 1,218 total
includes taxes & fees
22 Jun - 23 Jun
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Exterior

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 SAR 1,013
SAR 1,218 total
includes taxes & fees
22 Jun - 23 Jun
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Smart TV, fireplace, table tennis, books

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (132 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is SAR 1,363
SAR 2,548 total
includes taxes & fees
19 Jul - 20 Jul
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Fridge, microwave, oven, stovetop

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 SAR 760
SAR 2,000 total
includes taxes & fees
22 Jun - 23 Jun
Anne & Fred`s Leonardtown Home W/ Arcade room!
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 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 SAR 1,287
SAR 2,407 total
includes taxes & fees
22 Jun - 23 Jun
Charming Waterfront 3-bedroom house in Piney Point
Outdoor dining

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (36 reviews)
"Great spot"
United States
SHAWN W.
The price is SAR 1,704
SAR 2,960 total
includes taxes & fees
7 Jul - 8 Jul
Waterfront Reset: Views, Games, Boats & Total Calm
Interior

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is SAR 1,618
SAR 4,135 total
includes taxes & fees
29 Jun - 30 Jun
Lakefront Cabin near Solomons Island w/ Hot Tub
Property grounds

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, (12 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 SAR 1,734
SAR 3,239 total
includes taxes & fees
23 Jun - 24 Jun
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Property grounds

Secluded Woodland Waterfront Retreat

Secluded Woodland Waterfront Retreat
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"The host was very communicative, the house was very clean and comfortable, and the river views were beautiful!"
United States
Meghan H.
The price is SAR 1,233
SAR 2,194 total
includes taxes & fees
30 Jun - 1 Jul
Secluded Woodland Waterfront Retreat
TV, fireplace, video games, books

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, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is SAR 2,188
SAR 4,187 total
includes taxes & fees
28 Jun - 29 Jun
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is SAR 1,607
SAR 3,427 total
includes taxes & fees
5 Jul - 6 Jul
'the Bayside Escape' Remote Chesapeake Bay Estate
Smart TV, books

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 SAR 1,877
SAR 3,571 total
includes taxes & fees
22 Jun - 23 Jun
4-BR Waterfront Turret Home
House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is SAR 1,813
SAR 4,140 total
includes taxes & fees
23 Jun - 24 Jun
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Callaway Hotel Reviews

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

10/10 Excellent
"The staff at this Home 2 Suites was wonderful. They always greeted us with a smile and a cheery hello and let us know that they would help us in anyway possible."
Judith 5-night trip
Posted 1 hour ago
Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Frequently asked questions

Can I find a vacation rental in Callaway?

Yes, we have vacation rentals close to popular points of interest in Callaway, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Callaway has to offer?

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay: This vacation home rental near Callaway is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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 larger area, you’ll find Patuxent River Naval Air Museum and Patuxent River Naval Air Station.

What’s a vacation rental in Callaway like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Callaway. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.