Vacation rentals in Callaway

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Top-rated vacation rentals in Callaway

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Top guest favorite

Apartment in California

4.92 out of 5 average rating, 217 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Top guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 352 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

Top guest favorite

A coffee maker is positioned on a dark surface next to a stack of three mugs. The mugs display cheerful messages in orange, black, and white, reading 'Grateful,' 'Blessed,' and 'Espresso Obsessed.' The coffee maker features a sleek design with a digital display.

Place to stay in California

4.95 out of 5 average rating, 19 reviews

Modern | Bright | Cozy Private Room | Free Parking

Forget your worries in this spacious and serene room with a private bathroom and entrance. Relax in front of a big TV screen or get some work done. Ideal for early morning or late night walks. Safe and clean neighborhood. 5 minutes from Movie Theatre/(Dine-In/Take-Out) Restaurants/USM | 10 Minutes from Shopping Centers/Plazas | 15 Minutes from Solomon's Island/PAX River | 20 Minutes from CSM/SMCM | 45 Minutes from Dahlgren Naval Base | 1-1.5 Hour(s) from National Harbor/Washington DC/Virginia.

Top guest favorite

A wooden dock extends over the water, leading to a sun setting on the horizon. Waves gently lap against the sides, reflecting warm hues of orange and pink as the sky transitions into dusk. Two benches are positioned on the dock, inviting peaceful contemplation.

Loft in Lusby

5 out of 5 average rating, 372 reviews

Treetop Loft Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction burner, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Guest favorite

Loft in Solomons

4.95 out of 5 average rating, 167 reviews

Stunning Waterfront Chef's Loft

Looking for a truly unique getaway? You've found it in the Chef's Loft. Located at the top of our recreational cooking school, it offers stunning panoramic water views from every window! While you're here, take part in one of our cooking classes. All guests receive a 10% discount. The loft is close to area museums, a sculpture garden, fishing, hiking trails, fossil hunting, wine tasting and more! Discover why Coastal Living Magazine named Solomons one of the "happiest places in America!"

Top guest favorite

A cozy bedroom features a wooden bed adorned with soft linens and decorative pillows. Warm string lights drape along the sloped ceiling, creating a gentle glow. Framed artwork and bedside lamps add character to the space, while the walls exhibit a calming blue hue.

Guest suite in Lusby

4.98 out of 5 average rating, 347 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Guest favorite

A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.

Cottage in Leonardtown

4.96 out of 5 average rating, 194 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Top guest favorite

An aerial view showcases a blend of natural landscapes and developed areas, featuring a winding road alongside greenery and water. Structures near the shoreline include buildings and marina facilities, with boats anchored in the harbor, surrounded by trees and fields.

Apartment in Lexington Park

4.97 out of 5 average rating, 132 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Superhost

A winding stone pathway is lined with landscaped greenery and accentuated by soft lighting. The path is framed by a white fence and features a mixture of rocks and plants, creating a tranquil outdoor space beside the cottage.

Home in Tall Timbers

4.89 out of 5 average rating, 123 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Immaculate cottage with old world detail and large stone patio. Easement to water to enjoy the fantastic Southern Maryland sunsets dipping beyond the Potomac River. Situated in St Mary’s County near Piney Point and St George’s Island. A short walk to Tall Timbers Marina. Boats and polite pets are welcome with prior approval. Central heat & air conditioning, Front-yard fire-pit, Fast Internet, Smart TVs, Cable 2 Plastic Kayaks Fully stocked Kitchen, and bedding Crab net Fish Table

Top guest favorite

Home in Piney Point

5 out of 5 average rating, 110 reviews

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Top guest favorite

The cottage's exterior features a spacious wooden deck with modern seating options, including a sofa and lounge chairs. Large glass doors provide an inviting view into the home, surrounded by greenery and trees. Natural light filters in, enhancing the outdoor setting.

Home in Leonardtown

5 out of 5 average rating, 117 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Top guest favorite

A serene outdoor seating area is framed by lush greenery and colorful flowers, leading to an expansive view of Breton Bay. A decorative lantern hangs from the pergola, enhancing the tranquil atmosphere of this inviting garden space.

Apartment in Leonardtown

4.98 out of 5 average rating, 136 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.