House holiday rentals in Woodstock

4.89 out of 5 average rating, 141 reviews

Sweet retreat is waiting for you!

Sweet Retreat is ready for a cozy winter getaway. Come spend the weekend with friends and family or have a much needed vacation. Lake Geneva has something for everyone. Our Sweet Retreat is a perfect location for winter activities and is a short drive to downtown Lake Geneva. Tons of bars and restaurants to enjoy and explore . Three ski resorts, tons holiday festivities, Santa cruise and much more located around the area. Our home is fully decorated and ready for your friends and family.

A welcoming living area is presented, featuring a spacious black sectional sofa and a cozy round chair. Natural light floods in through sliding glass doors, leading to an outside view. A subtle decor with plants and a table lamp adds to the inviting ambiance.

4.91 out of 5 average rating, 197 reviews

Lake Geneva cottage with private beach access

This 100 year old cute cottage is located just down the street from beautiful Lake Como that offers fishing, boating, and water sports. It is just a short drive to Lake Geneva and all it has to offer with its beautiful lake, shopping, historic buildings, and delicious restaurants. Along with the house you get access to the HOA covered private beaches and playgrounds nearby. There is also a bar and grill down the street with live music. Bring your family or your friends and welcome to my home.

4.95 out of 5 average rating, 207 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.

4.94 out of 5 average rating, 120 reviews

A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.

Home in Salem

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

A bright and open living area features large windows allowing natural light to fill the space. A modern dining table with white chairs sits adjacent to a cozy seating arrangement with a gray sofa and decorative pillows. A stylish fireplace adds warmth to the ambiance.

4.96 out of 5 average rating, 196 reviews

Renovated Luxury Retreat Near Lake•Peaceful Escape

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

The sunroom features large windows providing views of the serene pond and natural surroundings. Cozy seating areas with blue cushions are present, along with a coffee table at the center. A ceiling fan offers airflow, contributing to a tranquil atmosphere.

4.88 out of 5 average rating, 163 reviews

Charming Lake Geneva, Wisconsin 3BR/2Bath Home

Step into the comfort of this sun-soaked 3BR 2Bath home in a tranquil area in Lake Geneva, WI. This relaxing retreat with a picturesque private pond is immersed in a breathtaking natural ambiance offering a perfect escape from the big city crowds. The stylish design and rich amenity list will leave you in awe. ✔ 3 Comfortable Bedrooms ✔ 2 Living Areas ✔ Sunroom ✔ Fully Equipped Kitchen ✔ Patio with a grill ✔ Pond Access ✔ High-Speed Wi-Fi ✔ Smart TVs ✔ Board Games/ Learn more below!

4.96 out of 5 average rating, 223 reviews

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

4.99 out of 5 average rating, 129 reviews

The tranquil scene captures a vibrant sunset over the lake, reflecting hues of orange and gold on the water's surface. Silhouetted against the colorful sky, two ducks glide peacefully by the shoreline, framed by a quiet lake house and rocky beach area.

Home in Milton

Buoys UP! Lake Life & Sunsets

Looking to unwind & enjoy Lake Life-where weekends begin any day of the week-any season you choose? Here at Buoys UP! you will be able to do just that. Enjoy private access to our newly remodeled 2 bedroom lake house at Lake Koshkonong, WI. Overlook the private road this little gem is located on and enjoy the wonderful lake views and the beautiful sunsets. Stroll down the road for apx. a 2 minute walk to take advantage of your personal lake access Buoys UP! offers just for you.

4.99 out of 5 average rating, 195 reviews

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

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!

5 out of 5 average rating, 102 reviews

A grassy area features multiple wooden lounge chairs facing the lake. A small fire pit is positioned in the center. Behind, a light-colored shed and a dock can be seen, with boats and kayaks stored nearby. A vibrant sky with colorful clouds adds to the scene.

Home in Fox Lake

Wonderful Mineola Bay Lakefront Cottage 4adu+4kids

Book a romantic weekend or bring the whole family to this cozy, clean and well-appointed lake house that has plenty of room for fun. Embrace lake-life at its finest when you call this Fox Lake cottage on Mineola Bay your home away from home! We have a dock to park your boat, so bring it. Access to restaurants, bars, convenience and grocery stores, boat launches and more. Or hang out and soak in the sunshine while paddle boarding, boating, kayaking, swimming and nature hikes.

4.97 out of 5 average rating, 146 reviews

The cottage features a charming facade with a combination of blue siding and stonework. Two sets of double doors are framed by large windows, allowing natural light to fill the entrance. Flower beds line the pathway leading to the front door, enhancing the welcoming appearance.

Home in Elkhorn

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

Home in Fontana-on-Geneva Lake

A small potted plant sits atop a wooden shelf, accompanied by blocks that spell out 'WELCOME.' The blocks are arranged in a neat line, showcasing a modern and friendly presentation.

4.93 out of 5 average rating, 238 reviews

The Little Farm Fontana 5 min from Geneva Lake!

Cozy cottage less than 2 miles from Fontana Beach and the sought after Geneva Lake! Minutes away from The Abbey Resort and just across the street from Abbey Springs Golf course, relax in this beautifully located home away from home out in the country with the luxury of quick and easy access to shopping and dining. We are within 15 minutes of downtown Lake Geneva if you are planning a day trip or a night on the town.

Popular amenities for house rentals in Woodstock

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 13 reviews

Home in Bartlett

Elegant Executive Residence, Hot Tub/Pool/Parties!

Home in Fontana-on-Geneva Lake

The exterior of the cabin features a log construction with a green roof and a spacious front porch. A golf cart is parked in the driveway, surrounded by well-maintained landscaping and mature trees. Sunlight filters through the leaves, creating a serene atmosphere.

5 out of 5 average rating, 5 reviews

The Lodge |Golf Cart |Abbey Springs |Beach

A refreshing pool surrounded by a wooden deck is visible, complemented by several loungers for relaxation. Lush greenery frames the area, providing a serene backdrop. Colorful flowers in the foreground add a touch of vibrancy to the peaceful outdoor setting.

4.98 out of 5 average rating, 42 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

4.98 out of 5 average rating, 55 reviews

Home in Twin Lakes

#EnglishPrairieBnB | 4 Bedrooms | 2.5 Baths

4.89 out of 5 average rating, 87 reviews

The charming Victorian home features a welcoming front porch adorned with hanging flower baskets and a large American flag. A brick pathway leads through manicured hedges and colorful flower beds, enhancing the inviting outdoor space surrounded by mature trees.

Home in Woodstock

Grand 1800s Victorian Gem: Updated/by Downtown

A spacious living area features comfortable gray sectional sofas adorned with turquoise cushions. A light wooden coffee table is centered on a soft area rug. Soft lighting is provided by table lamps, and large sliding doors lead to an outdoor space with a view of greenery.

4.95 out of 5 average rating, 100 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

5 out of 5 average rating, 66 reviews

A two-story blue house is positioned on a spacious lawn, framed by green grass dotted with yellow flowers. A tree provides shade in the front yard, while a small porch with chairs welcomes visitors. The driveway leads to a single-car garage.

Home in Genoa City

Family Getaway near Lake Geneva Winterfest

5 out of 5 average rating, 27 reviews

A well-maintained in-ground pool is shown surrounded by a concrete deck and lush greenery. A wooden fence encloses the yard, offering privacy. Tall trees and shrubs provide a natural backdrop, while the bright blue sky adds to the inviting atmosphere.

Home in Crystal Lake

Hot tub. Heated Pool. In town location.

Weekly house rentals

5 out of 5 average rating, 47 reviews

A screened-in porch features a seating arrangement with plush chairs and a central table. Natural light streams through the screens, offering views of the serene lake and surrounding landscape. A ceiling fan hangs above, providing a comfortable breeze in the inviting space.

Home in Trevor

Lakefront 2BR w/ Kayaks + Paddle Boards | Dogs OK

5 out of 5 average rating, 22 reviews

Home in Burlington

Long Lake Retreat - Cottage in Burlington, WI

4.85 out of 5 average rating, 75 reviews

A spacious bed is adorned with white linens and accent pillows arranged against a dark, textured wall. Red rose petals are artfully placed in the shape of a heart on the bed. A marble nightstand holds decorative candles and a small vase with dried flowers.

Home in South Holland

Romantic Escape ~ Adult Playhouse w Exotic Dungeon

4.99 out of 5 average rating, 69 reviews

A single-story house is situated on a spacious lawn, bordered by a tree line. A front porch extends from the house, while a driveway provides access to a garage. Nearby, a small tree is visible in the yard, enhancing the serene outdoor space.

Home in South Elgin

Cozy home, private location.

Home in Lake in the Hills

The open living area displays a comfortable blue sofa paired with a glass coffee table, overlooking a spacious dining area set for six. A stylish light fixture hangs from the ceiling, while a mounted TV and an electric fireplace add a modern touch.

4.85 out of 5 average rating, 13 reviews

Modern 4BD Home in Lake Hills Pet friendly

5 out of 5 average rating, 6 reviews

Home in Island Lake

Onyx Oasis Waterfront Hideout!

4.93 out of 5 average rating, 72 reviews

Double French doors open to a scenic view of the lake, allowing natural light to fill the room. A plush, textured throw rests on the neatly made bed, and the calm water is visible beyond the balcony railing.

Home in Round Lake Park

Lake House Retreat Near Navy Base

5 out of 5 average rating, 17 reviews

A wooden deck is presented, furnished with a glass-top table and several chairs. Sunlight filters through nearby trees, illuminating the space. Kayaks and paddleboards are arranged along the shore, visible in the background, creating a connection to the outdoor activities offered by the lake.

Home in Fox Lake

Lakeside Getaway 2 King Beds

Private house rentals

4.84 out of 5 average rating, 37 reviews

An aerial view reveals a single-story home surrounded by lush greenery and manicured lawns. The backyard overlooks a golf course, showcasing a well-groomed fairway and a putting green. Nearby, two adjacent homes are partially visible, maintaining a cohesive residential appearance.

Home in McHenry

Spacious Ranch blocks away from Downtown McHenry

4.96 out of 5 average rating, 94 reviews

A wooden deck steps lead to the entrance of a recently renovated home, framed by flower pots and outdoor seating. Decorative string lights are visible above, and an American flag is displayed on the left, adding to the welcoming atmosphere.

Home in Salem

Lago Amore - Channel house, pier, kayaks

Superhost

A two-story home features a light-colored exterior with dark trim. The front yard is well-maintained, showcasing bright flower pots and green grass. The driveway leads to a spacious three-car garage. Large windows enhance natural light and views of the surrounding landscaping.

Home in Belvidere

4.86 out of 5 average rating, 7 reviews

Luxury & Comfort in a Large Home

4.91 out of 5 average rating, 65 reviews

The exterior of the home features a combination of stone and siding, with a spacious driveway leading to a two-car garage. The front yard is landscaped with shrubs and decorative gravel. Trees provide natural shade, while the sky displays soft orange and blue hues.

Home in Fox Lake

Waterfront - Fox Lake - Bring your boat. 3bd 2bath

4.92 out of 5 average rating, 93 reviews

The king bed is presented with a white linen cover and flowery pillows, situated in a serene, softly lit room. A cedar barrel sauna, made of warm-toned wood, is shown outside among trees. The waterfront features a wooden dock extending towards the calm lake, surrounded by autumn foliage.

Home in Spring Grove

Pelican LakeHouse w/boat slip & sauna (sleeps 4)

5 out of 5 average rating, 22 reviews

The exterior of the house is highlighted by a striking facade, featuring large glass windows that provide views of the sunset. A spacious deck and seating area are framed by landscaped stone steps and lawn leading to the firepit, enhancing the outdoor gathering space.

Home in Bristol

Blue Moon Lake House

4.9 out of 5 average rating, 21 reviews

An aerial view captures a serene neighborhood surrounding Cross Lake, with lush trees interspersed among residential homes. The glimmering lake reflects sunlight, bordered by green spaces and walkways, creating a peaceful setting for outdoor activities.

Home in Salem Lakes

Twin Pines at Cross Lake