Vacation rentals in Woodstock

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Top-rated vacation rentals in Woodstock

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Guest favorite

Apartment in Sykesville

4.96 out of 5 average rating, 130 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.

Jul 26 – Aug 2

G$19,515 GYD per night

Guest favorite

Guesthouse in Glenwood

4.94 out of 5 average rating, 160 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.

Nov 22 – 29

G$37,853 GYD per night

Guest favorite

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.

Jul 9 – 16

G$23,607 GYD per night

Guest favorite

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.

Jul 7 – 14

G$23,917 GYD per night

Guest favorite

Guesthouse in Owings Mills

4.97 out of 5 average rating, 119 reviews

Shamrock cabin with hot tub, large yard

Please no cats! We are allergic. Backyard tiny house/guest house fits 2 adults comfortably. Equipped with small kitchenette, queen bed, and private bathroom. Kitchenette equipped with mini fridge, toaster oven, microwave, Keurig coffee machine, and silverware/dishware. Snacks/breakfast items and assorted k-cups provided. Dog friendly with spacious enclosed back yard containing private hot tub, small above ground pool, propane grill, fire pit, and badminton net. Includes Wi-Fi & TV with roku.

Jun 24 – Jul 1

G$19,112 GYD per night

Guest favorite

Guest suite in Catonsville

4.94 out of 5 average rating, 470 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Sep 6 – 13

G$20,229 GYD per night

Guest favorite

Guesthouse in Catonsville

4.96 out of 5 average rating, 198 reviews

Fox Cottage *Pet Friendly*

Fox Cottage is a modern addition to our 115 year old Victorian home. It’s a One Bedroom Queen size mattress & memory foam topper. There’s a Loft with a Full Size Memory Foam Mattress. The loft is a cozy space accessible by a vintage wooden ladder. We have multiple types of pillows for you to choose from. Hypoallergenic sheets are available upon request. There’s an outdoor seating area with a Chiminea to light a fire, enjoy a cup of coffee or wine, work or just listen to the birds.

Mar 2 – 9

G$32,566 GYD per night

Guest favorite

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!

Jul 21 – 28

G$22,659 GYD per night

Guest favorite

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.

Nov 28 – Dec 5

G$32,272 GYD per night

Guest favorite

Guest suite in Silver Spring

4.89 out of 5 average rating, 141 reviews

Private guest suite in a newly remodeled home

You'll find a spacious and bright basement apartment that has a bedroom with a queen-size bed, a couch, toilet and kitchenet, all in the suite. It has its own entrance and self check-in. It is complete with a flat-screen TV and an office desk for your work. None of the amenities are shared with other guests. The fully-equipped kitchenet has everything you'll need to cook and warm your meals, including a fridge, microwave, stove, and all the pots, pans, and utensils.

Aug 28 – Sep 4

G$19,228 GYD per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 263 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.

Jul 30 – Aug 6

G$26,832 GYD per night

Guest favorite

Apartment in Sykesville

4.97 out of 5 average rating, 279 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!

Dec 13 – 20

G$19,219 GYD per night