Places to stay in Woodstock

4.99 out of 5 average rating, 72 reviews

Loft in Woodstock

The Lux Loft~Walk to Square/Train Link to Chicago

Welcome to The Lux Loft! Savor a posh retreat in the privacy of this exquisite timber loft. Charming Woodstock (Bill Murray's "Groundhog Day") offers guests Victorian town-square nostalgia and artisan boutiques. The train station is just two blocks away to whisk you away away from the city or towards Chicago/airport. Or enjoy scenic drives through the horse country of Bull Valley Lake and the resort town of Lake Geneva. Luxuriate in fine furnishings and elegant French/urban/industrial decor.

4.96 out of 5 average rating, 197 reviews

A vibrant farmers market scene is captured, featuring a table adorned with colorful bouquets and fresh flowers. Market-goers are seen browsing the stalls, while a dog accompanies one visitor. A canvas awning provides shade over the flower displays, enhancing the lively atmosphere.

Loft in Woodstock

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

5 out of 5 average rating, 127 reviews

An inviting outdoor space is illuminated by string lights, creating a cozy atmosphere. A large dining table is surrounded by comfortable chairs, with colorful cushions adding a pop of color. Lush foliage and a fenced yard provide a private setting for relaxation.

Apartment in McHenry

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Apartment in Crystal Lake

A spacious outdoor area is featured, with several patio tables and chairs arranged around a central fire pit. The two-story building, painted in warm tones, includes outdoor seating on a deck that overlooks a sandy beach and lush greenery in the background.

4.96 out of 5 average rating, 116 reviews

Farmhouse Chic Home with a view. Downtown

Charming Historic Apartment in Downtown Crystal Lake Spacious second-floor apartment overlooking Downtown Crystal Lake, located in a vintage 1875 farmhouse. Steps away from over 100 restaurants, shops, coffee spots, and bars, all within a 2-minute walk. Enjoy updated bedding, modern comforts, and vintage finishes in a quiet space with no shared walls or upstairs neighbors. One parking space included, with additional lot park CHECKOUT OUR OTHER PROPERTIES HERE: www.airbnb.com/p/breganproperties

4.96 out of 5 average rating, 368 reviews

The entrance to the loft is seen through an open door marked with 'One.' A narrow hallway features warm hardwood flooring, exposed brick walls, and several framed art pieces on the walls. Natural light enters from windows at the end of the corridor.

Loft in West Dundee

Hip Urban Loft-Small Town Charm - 124 LOFTS #1

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Book one Loft or all four.

4.95 out of 5 average rating, 191 reviews

An aerial view captures a sprawling five-acre property surrounded by a lush woodland forest. The landscape features a well-maintained green lawn with several trees and pathways, along with multiple buildings nestled together, offering a sense of tranquility in nature.

Home in Harvard

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

4.99 out of 5 average rating, 659 reviews

The exterior of the home features light-colored siding and red shutters, complemented by neatly trimmed shrubs. A stone pathway leads to a white front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the entrance.

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Farm stay in Cherry Valley

A well-lit bathroom features a spacious vanity with multiple drawers and a sink. A frosted glass shower stall is positioned in the corner, while decorative toiletries are placed on the countertop. Neutral-colored tiles cover the floor, and a mirror reflects the room's light.

4.97 out of 5 average rating, 361 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

5 out of 5 average rating, 28 reviews

Tiny home in Harvard

Tiny House on Horse Farm

Tiny house sits on the back of a beautiful horse farm out in the country . House sits on the back five acres of Sheetz farm. Your only neighbors are deer, foxes, eagles, owls, sand hill cranes, and wild turkeys. Tiny house sits on the bank of a small pond. You also have access to five acres of woods with marked trails. The property that the house sits on might be the most peaceful spot on earth. Tiny house means just that, it’s TINY, approximately 180 square feet. Owners live on site.

4.79 out of 5 average rating, 121 reviews

A spacious deck is seen with a blue umbrella providing shade over a table surrounded by several chairs. A view of the Fox River is visible, showcasing boats moored along the shore and greenery lining the opposite bank.

Apartment in Algonquin

Waterfront Stay w/ Walk to Downtown Entertainment

Apartment overlooking the Fox River. Walking distance to downtown Algonquin. Free wifi & cable TV. Don't impose on family or friends, or settle for the bland experience of a box hotel. Instead, book a comfortable stay with great amenities and enjoy the river and downtown entertainment. (be sure to see our guidebook!) You'll be able to relax, get a restful sleep, and enjoy your visit. You'll also notice the little touches and the extra effort made to assure you have an awesome stay.

4.95 out of 5 average rating, 177 reviews

A historic stone home built in 1911 is prominently featured, showcasing its grand architectural details. The façade includes a porch supported by strong columns. A group of individuals stands in front, illustrating the home's welcoming presence in its early days amidst a natural landscape.

Guesthouse in McHenry

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

4.99 out of 5 average rating, 148 reviews

A cozy seating area features a gray sofa and a small table with decorative items. Natural wood walls add warmth, while large sliding glass doors frame the serene lake view, leading to an outdoor deck overlooking the water.

Home in Round Lake Beach

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

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Popular amenities for Woodstock places to stay

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Woodstock

4.88 out of 5 average rating, 130 reviews

An airy living space is highlighted by large windows offering views of the lake. A wooden dining table accommodates six, while a comfortable seating area is arranged around a fireplace. A large flat-screen TV is mounted above the fireplace, enhancing the room's modern aesthetic.

Home in Fox Lake

Lakefront Paradise

4.92 out of 5 average rating, 272 reviews

A bright and airy living area features a white-beamed ceiling and large windows that allow natural light to fill the space. Comfortable seating includes two soft couches, with a wooden coffee table at the center. A dining area with a large table and wicker chairs is visible in the background.

Home in Kenosha

Hot tub getaway Extra Large capacity home

Apartment in Jefferson Park

A modern dining area is highlighted by a wooden table surrounded by four chairs. The open-concept layout connects to a stylish kitchen featuring dark cabinetry and stainless steel appliances. Natural light fills the space, reflecting off the hard surface flooring and a cozy living room in the background.

4.64 out of 5 average rating, 28 reviews

City Gem: Stylish 3BR for Urban Explorers

5 out of 5 average rating, 9 reviews

A screened porch features ample seating arrangements with wicker chairs and a modern grey sofa. A geometric-patterned rug covers the floor, and a small table is placed beside the sofa. Natural light filters through the glass roof, creating a bright and inviting space.

Home in Silver Lake

Near Lk Geneva- Fun 5 mins Hiking Biking Bch & ski

4.92 out of 5 average rating, 349 reviews

A firepit is encircled by a decorative metal border featuring nature-inspired designs. Two wooden Adirondack chairs are positioned nearby, overlooking a grassy area surrounded by trees. Smoke rises gently from the glowing embers, suggesting a cozy gathering space.

Cabin in Trevor

Living the Lakehouse Dream

4.85 out of 5 average rating, 68 reviews

Home in Austin

A Comfortable Stay While You are Away in Oak Park

5 out of 5 average rating, 10 reviews

A modern cabin exterior is shown, featuring a light wood deck with comfortable seating arranged around a small table. Decorative string lights add ambiance above the space, while lush greenery and trees line the background, creating a peaceful outdoor environment.

Cabin in Antioch

ELK Cabin on Petite Lake, Ol Pine Lodge Cabins