Holiday rentals in Cooksville

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Top-rated holiday rentals in Cooksville

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Guest favourite

Flat in Sykesville

4.96 out of 5 average rating, 131 reviews

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

15–22 Aug

₹7,966 per night

Guest favourite

Guest house in Glenwood

4.94 out of 5 average rating, 161 reviews

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

1–8 Apr

₹15,348 per night

Guest favourite

Guest suite in Derwood

4.98 out of 5 average rating, 179 reviews

Cozy, Private Garden Apt in Derwood-La Belle Vie

Spacious one bedroom basement apartment. Private entrance, full bathroom and kitchenette all newly done. Newly landscaped slate patio with garden and pond. The sound of running water provides a relaxing environment. Secluded back yard backs up to beautiful woods. 5 min away from bike trails. Large, open living space with sectional couch, and attached eating area with a table that can double as a work station. Centrally located in Montgomery County-approx 40 minutes from DC/Baltimore/Frederick.

1–8 Jul

₹9,213 per night

Guest favourite

Tiny home in Glenwood

4.9 out of 5 average rating, 130 reviews

Ellerslie cabin

Located in Glenwood, Maryland, Ellerslie is a 50 acre farm which dates back to 1763 with scenic views, fields of corn and a tranquil stocked pond. Nestled here is a small historic log cabin, built around 1810, that is charming and cozy. It has recently been restored and is equipped with all modern amenities, including a new stainless steel refrigerator and gas stove. The cabin is perfect for a business person who prefers staying in the country to a city setting or for a weekend getaway.

4–11 Oct

₹9,634 per night

Guest favourite

Guest suite in Woodstock

5.0 out of 5 average rating, 143 reviews

Our Retreat -in a country setting.

Private- apartment in the lower level of our house. House is in a rural setting- you may spot a few white tail deer or other wildlife. Come here and enjoy the peaceful tranquil setting. We are within 5 minutes to Rte 70 and shopping centers. Over 1800 sq. our space isn't childproof. Workout equipment available for use at your own risk. We control the HVAC and will adjust as requested. May not be suitable for those with mobility issues due to the walk to the entrance. We don't allow smoking.

16–23 Oct

₹9,751 per night

Superhost

Home in Sykesville

4.82 out of 5 average rating, 132 reviews

Plummer Farmhouse

Want to experience historic Sykesville living? Look no further! This 1892 charmer offers 5 bedrooms and 2.5 baths with over an acre of land and amazing outdoors space (TV, over sized deck, and rail road tracks!). In 2016 Sykesville was named The Coolest Small Town in America and now you get to experience all its "coolness". The farmhouse is located only steps away from the Main Street which hosts boutique shops, great restaurants, distillery, farm markets and trout fishing in Patapsco river.

8–15 Apr

₹20,546 per night

Guest favourite

Loft in Walkersville

5.0 out of 5 average rating, 131 reviews

Daysville Inn- Boho Farmhouse Apt

This farmhouse apartment is perfect for your next visit to the Walkersville/Frederick MD area! Peacefully private from the hosts’ home, and conveniently located just 2 miles from the popular Walkers Overlook Wedding Venue, and 7 miles from the fun downtown Frederick! With many popular breweries/wineries surrounding it, it’s your perfect weekend getaway! It even comes with 4 friendly goats our guests are welcome to pet! No hotels are closer! We hope you book your stay today at Daysville Inn!

25 Oct – 1 Nov

₹8,708 per night

Guest favourite

Guest house in Monrovia

4.95 out of 5 average rating, 110 reviews

Poolside Paradise in Monrovia, Maryland.

Enjoy your stay in this fabulous pool house located in a quiet neighborhood. Relax poolside during the day and enjoy the outdoor bar and kitchen for cocktails at sunset. Breathtaking views all around. Just 50 minutes from Baltimore and Washington DC and 10 minutes to historic downtown Frederick. Private entrance to backyard with a large green space on the backside of the pool house. We consider ourselves a couples retreat and don’t host gatherings. We look forward to hosting you soon:)

11–18 Oct

₹18,276 per night

Guest favourite

Guest suite in Randallstown

4.99 out of 5 average rating, 106 reviews

Private Efficiency Suite ~ King Bed ~ Baltimore Co

Welcome to Hickory Roots Hideaway! A cozy yet spacious 750 sq ft efficiency guest suite situated on our picturesque 4 acre homestead! Great Wi-Fi and amenities make this a perfect getaway even if work and virtual school must continue. Enjoy a relaxing stay - you are welcome to explore our garden, shoot some hoops in our basketball court, or get to know our adorable farm animals. We are conveniently located with easy access to I-70, I-795, and just 30 minutes from downtown Baltimore!

6–13 Aug

₹9,248 per night

Guest favourite

Cottage in Woodbine

4.91 out of 5 average rating, 125 reviews

Gate House

Quaint cottage farm house nestled in beautifully rolling countryside setting on an operating horse farm. Fully furnished with all the modern amenities. Easily accessible from I70, and located within 30 to 40 minutes of Frederick, Baltimore, DC and Gettysburg. This property is also situated at the North west trail head to the Patuxentstate park, with tons of access to easy hiking! Pet friendly, we just ask that pets remain on leash when outside of the space or vehicles.

13–20 Dec

₹13,157 per night

Guest favourite

Guest house in Highland

4.98 out of 5 average rating, 264 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

18–25 Oct

₹10,203 per night

Guest favourite

Flat in Sykesville

4.98 out of 5 average rating, 281 reviews

In the Heart of Sykesville! 2 Bedroom Suite

Located in the heart of Sykesville, Linden, a two bedroom basement suite, welcomes you to relax and rewind! We have designed our space to feel like your home away from home.The kitchenette includes a full refrigerator, microwave, slow cooker, Instapot, and a hot plate for meal prep. An easy stroll to Main Street will give your car a rest as you enjoy dining and shopping, live music from May/Oct and a wonderful Splash Park from May/Sept. Discover our hidden gems!

31 Aug – 7 Sep

₹7,836 per night