
Holiday houses in Woodstock
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Top-rated holiday rentals in Woodstock
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Our Retreat -in a peaceful setting.
Private- apartment in the lower level of our house. House in a rural setting- you may spot white tail deer or other wildlife.Enjoy the peaceful tranquil setting.We are within 5 minutes by car to Rte 70 and shopping centers. 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. Non smoking. We aren't set up for heavy cooking. No stove.

Heart of Sykesville! 2 Bedroom Suite! Walk to town
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. Private guest patio with small gas grill. Dogs considered.

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.

Annapolis Garden Suite
Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a private ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a deadbolt; no shared indoor spaces; separate entrances).

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!

Cute cottage studio with full kitchen and laundry
Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Historic Hillside Cottage
Experience the charm of an 1800s home styled with modern amenities. This historic cottage is steps away from all that Historic Ellicott City has to offer. Spend the day exploring Main Street lined with restaurants and small businesses or go for a walk, hike, bike ride or swim in nearby Patapsco State Park. Perfect for guests in town for weddings, concerts or those that love history and nature. Centrally located with easy access to Columbia, Baltimore & Washington D.C.

Tiny A-Frame Retreat in the Woods
Beautiful, quiet woodland setting with a creek running through it, just 5 miles from downtown Frederick. Tucked away into the woods our tiny A-Frame has a comfortable queen bed(not an air mattress) for a rest and retreat fully immersed in the poplar woods. This is a camping style set up- so if you enjoy camping then this place is for you. No running water- but plenty of good clean mountain water available , no electricity, compost toilet. We do not allow dogs.

Quiet Luxury Home - Modern - King - 20 Min from DC
Completely new renovations with an eye for details have created a space that feels like a custom built home. Made to provide you with a memorable luxury rental experience. Comfortable, bright, modern, unique and stylishly furnished mastering the mix of timeless elegance and modern simplicity. An open floor plan space that’s equally welcoming and sophisticated, incorporating natural elements, layered fabrics, and textures.

The Garden Studio
Thoughtfully appointed 1 bedroom guesthouse in beautiful Greenspring Valley. Enjoy quiet quarters on an acre of private residential property within 5 minutes of the Baltimore beltway & restaurants, grocers, gas, and services. Close to Stevenson University (2 mi), Towson University (7 mi), convenient to other colleges & universities in the area; and 11 mi to the Inner Harbor. Host available in main house as needed.

Coastal Waterfront 1 Bedroom Cottage
This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Historic Gatehouse Master Suite
Discover the historic charm of Maryland's scenic horse country! Our Master Suite, part of a Tudor-style gatehouse on a country estate, offers luxury and convenience. Minutes from Hunt Valley and Baltimore, indulge in a Carrera marble bathroom, a private deck with sweeping views, a full-size tennis court, a refreshing pool, and more. Immerse yourself in elegance and history.
Popular amenities for Woodstock holiday rentals
Other great holiday rentals in Woodstock

Elegance at Emerald

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

Lyonswood Haven

Chic style space near Columbia

Tree house resort spa with sauna

Welcome to Heron House! Annapolis Waterfront Oasis

NEW Family/Pet Friendly, fenced in yard with Pool!

Gillis Carriage House 1 BR entire place pond view
Destinations to explore
- Georgetown University
- Walter E Washington Convention Center
- National Mall
- The White House
- Nationals Park
- M&T Bank Stadium
- District Wharf
- Baltimore Convention Center
- National Museum of Natural History
- Capital One Arena
- Oriole Park at Camden Yards
- Liberty Mountain Resort
- Stone Tower Winery
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Sandy Point State Park
- Washington Monument
- Betterton Beach
- Georgetown Waterfront Park
- Patterson Park
- National Harbor
- Johns Hopkins University
- The Anthem




