Cottage vacation rentals in Winnetka

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Winnetka

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

Cottage in Highland Park

4.98 out of 5 average rating, 87 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Step inside Step back in time Cozy, 1880 built, re-imagined, ravine edged garden cottage Your home away from home. Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage yet modern, Mere Cottage has so much to offer. Inside: You'll enjoy updated amenities in harmony with a distinctive vintage charm. The common area has an open layout, perfect for socializing. The kitchen and pantry (my favorite room!) are new from top to bottom and are fully stocked with any cooking gadgets you may need. Two bedrooms are joined by a Jack & Jill bathroom. The living room has a sofa that pulls out into full size bed. Outside: Jordan and I had fun redesigning the grounds from front to back. Enjoy the front garden from the rocking chair on our wrap around porch. Out back we've added a vegetable and perennial garden for you to take in. Dinner out on the back deck overlooking the garden is highly recommended! Guests have access to the entire home and grounds. Jordan and I live in the neighborhood and will be available if you need us! Our cottage is located in Highland Park, about 25 miles north of Chicago on Lake Michigan. We like to think we have the best of both worlds- being in a quiet residential neighborhood with walking access to numerous amenities right around the corner. We're a quick 5 minute walk to Highwood (the north shore’s restaurant district) and an 8 minute walk to the Metra train that can take you from Chicago to Kenosha and any place in between. We're also right on the North Shore bike path (bring your bikes!). Fort Sheridan is also close by and worth exploring for its interesting history, architecture, and nature trails. On foot: Many errands can be done on foot. We have some of the best restaurants and watering holes north of Chicago within walking distance. There is also a Walgreens convenience store 2 blocks away. By car: Getting around by car is also easy. Parking is readily available almost anywhere you'll visit. You can get to downtown Chicago in 30 minutes in ideal traffic. Train: The Metra (our train system) can also conveniently get you to and from various attractions including downtown Chicago (a scenic 45 minute ride), Ravinia music venue, the Chicago Botanic Gardens, Great Lakes Naval Base and many more. Bike: Pack your bikes! We're located on the north shore bike trail. Head north on the trail to check out the beautiful Fort Sheridan, Lake Forest, and quaint Lake Bluff. Head south to Ravinia, Chicago Botanic Garden, and numerous other beautiful villages along Lake Michigan. I bike often and will gladly point you to some great hidden gems! If you're flying into O'hare, we recommend taking an Uber to our cottage. We're about a 30 minute drive from the airport. Six Flags Great America is also a 25 minute drive away. Keep in mind that the bathroom is a Jack & Jill and is accessed from either bedroom. There is no access from the common area, so it could pose an issue at night when sleeping our max number of 6. Please keep things tidy and wash any dishes used during your stay. Out of respect for our neighbors (this home is located in a quiet residential neighborhood), no parties or large gatherings are allowed. No pets allowed.

Guest favorite

Cottage in Lake Villa

4.8 out of 5 average rating, 166 reviews

Laura’s Little Cottage

First, I’d like to mention this is located in a QUIET neighborhood. I don't rent out for big, loud parties. If that's what you're looking for, this is not the place for you. I like to keep peace with the neighbors! Moving on. This little cottage is just minutes from several forest preserves, the Chain O’ Lakes, Great America or Wilmot Mountain. 30 minutes to Great Lakes Naval Base & less than an hour to Lake Geneva, Chicago or Milwaukee. Plenty of restaurants, & grocery stores. 30 day minimum

Guest favorite

Cottage in Fox River Grove

4.86 out of 5 average rating, 28 reviews

Waterfront Cottage/sauna/kayaks/firepit/dock

Enjoy some time away at this peaceful cottage on the Fox River. There is a dock with jet ski lift and kayaks available to guests. Large deck with ample seating. There is a sand beach with volleyball court and playground within walking distance of home. Many places to dine and shop nearby. Some nice resteraunts on the water. Local attractions nearby including Norge Ski Club, Bettendorf Castle, Three Oaks Rec, ect. Fire pit next to river with wood included. Amazing sunset view and steam sauna.

Cottage in Fox Lake

4.94 out of 5 average rating, 17 reviews

Lakefront Cottage with Gorgeous Sunsets

Great cottage so close to the water you can fish right off the deck, bring your boat right up to the dock and drive it all over the chain of lakes and out to dinner. Endless things to do on the chain, tons of restaurants, sand bars, fishing, bars, boats, etc. Then, watch the sunset at the beach right outside your door before retreating for the night into the cottage. The yard is fenced in, with a fire pit and is shared with permeant residence and another house I air bnb but is yours to enjoy

Guest favorite

Private room in North Riverside

4.93 out of 5 average rating, 226 reviews

The Albany Park Room at the Cape Cod in Riverside

The Cape Cod in Riverside is 10 miles from downtown Chicago, accessible via METRA and CTA Blue Line. It's a block from a trail entrance, a mile from Brookfield Zoo, and close to Riverside's historic downtown and Loyola University Medical Center. O'Hare Airport is 18 miles away, and Midway is 9 miles. The Albany Park Room, one of two Airbnb listings, is on the second floor and accommodates two guests. The property supports sustainability with partial solar energy for heat and hot water.

Guest favorite

Cottage in Fox Lake

4.83 out of 5 average rating, 6 reviews

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

Situated right along the tranquil waters of Mineola Bay, this 2-bedroom, 1 full bath, 2 half-bath cottage boasts easy access to countless waterfront activities. Featuring a fire pit, 2 spacious decks, and 2 kayaks, this serene property is the perfect place for a nostalgic lake escape with plenty of outdoor adventures! When you're ready to cool off, head inside to enjoy some competition at the foosball table or snuggle up by the fire for a relaxing night at this charming home.

Top guest favorite

Cottage in Barrington

5 out of 5 average rating, 111 reviews

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Guest favorite

Cottage in McHenry

4.94 out of 5 average rating, 52 reviews

Lakefront Views, Free Water Sports!!

Relax at this stunning lake house on Lake Pistakee. Enjoy this cozy house with a private lakefront view on a sleepy dead end street. This lake house underwent a full rehab in 2019. House features its own private dock right on the water and includes 2 free kayaks, 2 free paddle boards, and a free paddle boat to use. Enjoy the fire pit overlooking the water and free gas grill (byow). Lake Pistakee is on the Chain o Lakes which includes 14 connected lakes

Cottage in Fox Lake

4.81 out of 5 average rating, 180 reviews

All Season Sunset Cottage on Pistakee Lake

Escape to the beauty of the Chain O'Lakes to spend the weekend or a lengthy stay on the shores of Lake Pistakee. Enjoy our lakefront (west facing) cottage with enough beds to sleep 6. Our home is the perfect getaway to enjoy everything from fishing & water sports to dining and nightlife and even snowmobiling and skiing in the winter. Or maybe its for no reason at all except to simply relax lakeside and relish the breathtaking views.

Cottage in Skokie

New place to stay

Chic 2BR Cottage | Free Parking, Near Shops/Eats

Step into our bright and modern 2-bedroom retreat in Skokie, where comfort meets convenience. Just minutes from Old Orchard Mall, local dining, and public transit, this thoughtfully designed home features a fully stocked kitchen, cozy living area with smart TV and Wi-Fi, plush bedding, private entrance, and free parking. The perfect base for families, business travelers, or anyone looking to stay near Chicago.

Superhost

Cottage in Spring Grove

New place to stay

Lakefront 2BR Nautical Cottage with Hot Tub

Welcome to your perfect lakeside cozy cottage getaway! This newly remodeled 2-bedroom, 1-bath cottage sits just 60 feet from the scenic shoreline of Grass Lake on a shared resort property. Nautically decorated and thoughtfully updated, this cozy cottage offers the best of year-round lake living—whether you're soaking in the hot tub after a day on the water or gathered around the firepit under the stars.

Cottage vacation rentals in Winnetka

Top-rated cottage rentals in Winnetka

Vacation rentals for every style

Popular amenities for Winnetka cottage rentals

Cottage rentals with a hot tub

Pet-friendly cottage rentals

Private cottage rentals

Destinations to explore