Callaway Holiday Rentals

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Holiday Rentals in Callaway

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (73)
"Absolutely perfect location to get away for the weekend. It was so peaceful and we saw osprey and deer in the back yard. You have access to a dock which is fantastic at night to see the stars. The house has everything you could need. They have 2 kayaks we intended to use but ran out of time. The best part was sitting outside at night with a fire. Would absolutely stay again! "
Waterfront Cottage in Beautiful Hoopers Island

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (116)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (69)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Waterfront 3-Bed Oasis Perfect for City Getaway

10.0 out of 10, Exceptional, (11)
"My family and i enjoy our stay. The lake was so beautiful"
Waterfront 3-Bed Oasis Perfect for City Getaway

Waterfront Solomons Apartment

9.4 out of 10, Exceptional, (9)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is NZ$440
includes taxes & fees
11 Aug - 12 Aug
Waterfront Solomons Apartment

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

10.0 out of 10, Exceptional, (53)
"All around very clean, quiet and enjoyable place to stay."
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (119)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (166)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

9.8 out of 10, Exceptional, (30)
"Great stay, clean & owner gave great local suggestions!"
Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

Hays Beach House - Hot Tub - Private Beach

9.6 out of 10, Exceptional, (8)
"Stayed with two other families for the State Swim Championships. Property is spacious, clean and well appointed. Even the kitchen knives were sharp!"
Hays Beach House - Hot Tub - Private Beach

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

10.0 out of 10, Exceptional, (13)
"We stayed for a long weekend at the Summerlin Home, and loved it. All of the small details made the trip so much more enjoyable. From the single use toiletries in the bathroom, to the fully stocked kitchen with all of the essentials no detail was overlooked. It was a vacation rental that felt like home. The host were amazing, and extremely accommodating. It seemed they genuinely cared if we had a good trip, and were willing to help make it better if need be. "
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Tiny, Funky, and Full of Love - Welcome to the Love Shack

10.0 out of 10, Exceptional, (3)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
Tiny, Funky, and Full of Love - Welcome to the Love Shack

Waterfront home where you can relax or enjoy the things the Northern Neck.

9.8 out of 10, Exceptional, (9)
"Sandy was a wonderful and very responsive host. She made sure we felt very welcomed and 'at home' in this lovely house on the water. The home and owners made this a trip we'll remember."
The price is NZ$489
includes taxes & fees
18 Aug - 19 Aug
Waterfront home where you can relax or enjoy the things the Northern Neck.

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.8 out of 10, Exceptional, (6)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock

Cozy Cottage with access to and partially obstructed views of the bay.

9.2 out of 10, Wonderful, (25)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (25)
"This was the perfect house for our family trip to St. Mary's -- nicely upgraded, well stocked and beautiful views. Will definitely return."
Your private beach retreat in historic St. Mary's

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (30)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is NZ$520
includes taxes & fees
27 July - 28 July
Soul Oasis - home on the Chesapeake Bay

Where peace is sitting by the moonlight

9.6 out of 10, Exceptional, (91)
"Property was as expected. Enjoyed the quiet area - relaxing visit !"
Where peace is sitting by the moonlight
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

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?

Waterfront 3-Bed Oasis Perfect for City Getaway: This holiday home rental outside of Callaway is located on a river, and has a fireplace, a patio 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 can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Callaway?

While exploring the area, visit family-friendly sights like Kinsale Museum, 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.