Cottage holiday rentals in Countryside

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Top-rated cottage rentals in Countryside

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Top guest favourite
The cottage showcases a charming front porch adorned with white railings and lush green planters. Colorful flowers bloom in the garden, adding vibrancy to the landscape. The peaked roof and decorative gables enhance the inviting exterior, framed by trees providing a serene atmosphere.
Cottage in Highland Park
4.98 out of 5 average rating, 96 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.

Top guest favourite
A modern kitchen features white cabinetry and stainless steel appliances, including a microwave and coffee maker. A large central island with a marble countertop provides ample space for meal preparation. Natural light floods the area through various windows, enhancing the clean design.
Cottage in Saint Charles
5 out of 5 average rating, 34 reviews

Adorable 2 bedroom Cottage on the Fox River.

This unique 1928 riverside cottage is tastefully decorated and clean to ensure a 5 star stay. 2 bd 1 bath, Full kitchen, with everything you will need to prepare meals. Though the cottage is small in sq footage it's so much larger in person. Both bdrms provide a queen size bed with ample space. Perfect weekend getaway. Located on the Fox River with miles of boatable water. Minutes to downtown St. Charles and Geneva, Walking/paths, Restaurants and Shopping. 5 mi to Lamplight Equestrian Center.

Top guest favourite
A private wooden deck features a spacious hot tub with steps for easy access. Soft outdoor lighting creates a cozy ambiance, illuminating nearby trees and the charming cottage structure visible in the background. Green foliage enhances the serene setting.
Cottage in Gary
4.96 out of 5 average rating, 82 reviews

SYLVIA's CHARMING & RELAXING COTTAGE

Escape to beautiful Miller Beach! It is in a very friendly community, and the charming cottage is located only a 5min walk from the stunning beach. This house has a very private deck with an outstanding view of the green scenery, and the jacuzzi is also ready to be jumped into throughout all seasons. Walks on the beach here are very relaxing, as you will find the sugar-like sand to be pristine. When you stay at this cottage, you will never want to leave! You will enjoy and relax here for sure!

Guest favourite
A spacious back deck is highlighted, featuring an outdoor table with an umbrella and comfortable seating. A charcoal grill is positioned nearby, and vibrant flowers add a splash of color. The neighboring structures and lush greenery create a welcoming outdoor space.
Cottage in Fox River Grove
4.86 out of 5 average rating, 36 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.

Top guest favourite
The cottage exterior showcases a single-story structure with a light grey facade and a newly roofed design. Large windows allow natural light to enter, framed by a lush green landscape. A welcoming entryway leads to the home, complemented by garden pots and a gentle pathway.
Cottage in Gary
4.95 out of 5 average rating, 209 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is a one bedroom romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Superhost
The exterior of Miller Cottage features a striking red facade with modern midcentury architecture. A stone chimney adds character to the entrance, partially shaded by lush greenery. A manicured lawn and a paved driveway enhance the inviting atmosphere of the home.
Cottage in Gary
4.82 out of 5 average rating, 196 reviews

Midcentury Cottage 3bd IN Dunes Natl Park, Lake MI

If you're looking for a laid-back [aka not fancy] getaway, this is it. The Midcentury Miller Cottage features 3bd, 1ba, and has the perfect blend of updates and original midcentury modern details that will make you swoon. Home feels private and faces a wooded dune. Beach and restaurants are a 9-min walk away. More restaurants, beaches and hiking are a short car drive away. Take time at Miller Cottage to unwind, reconnect and explore. Located in the 61st National Park, Indiana Dunes.

Superhost
A comfortable living area features a spacious sofa with neutral-toned cushions. A glass coffee table sits atop a decorative rug, and wooden shelves display books. Natural light enters through window treatments, complemented by patterned curtains and a floor lamp.
Cottage in Wilmington
4.92 out of 5 average rating, 164 reviews

Get Your Kicks in Our Cozy Cottage Near Route 66

Enjoy all the comforts of home when you have to be away. Our fully furnished cottage is located 4 miles from Rt 53 / Historic Rt 66 and just blocks from the Kankakee River. Just 5 minutes to "downtown" Wilmington featuring restaurants, a wine bar, a local brewery, and multiple antique stores. ✧ Easy access to everything that Joliet has to offer just 20 miles away, including the Autobahn and Route 66 Raceway. ✧ 7 miles to easily access I55 for a quick ride into Chicago.

Top guest favourite
A charming cottage is framed by lush greenery and colorful flower planters. The white exterior features multiple windows, allowing ample natural light. A welcoming front porch leads to the entrance, adorned with patriotic bunting, inviting guests to enjoy the serene surroundings.
Cottage in Barrington
5 out of 5 average rating, 119 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!

Top guest favourite
The tranquil surface of Flint Lake reflects a colorful sunset, with soft hues of pink and orange blending into the serene blue sky. The surrounding tree line is silhouetted against the fading light, creating a peaceful and calming atmosphere.
Cottage in Valparaiso
4.93 out of 5 average rating, 434 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Escape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, fire pit, gas fireplace, tv, lake front, canoe, kayak, sauna, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life. Please note the pontoon boat is only available in season from May 1st to October 1st.

Top guest favourite
Cottage in Valparaiso
4.88 out of 5 average rating, 586 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Wood fireplaces (winter only!)

Guest favourite
A well-maintained exterior view of the cottage is displayed, featuring a neatly manicured lawn and bordered by trees. A private driveway leads to the entrance. The structure showcases a front porch area, and a fire pit is visible in the yard, inviting outdoor enjoyment.
Cottage in Merrillville
4.88 out of 5 average rating, 269 reviews

The Hideaway-An experience getaway!

NEW: Sauna & Jacuzzi! Welcome to your cozy cottage ESCAPE, a modern sanctuary 30 minutes from Chicago. This secluded private, detached cottage on a 3-acre property features a NEW SAUNA with Bluetooth & light therapy & JACUZZI (outdoor w/ privacy walls, a king-size bed, and a full kitchen. Enjoy your own yard, fire pit, and covered parking. A perfect blend of comfort and convenience. Single, or couples only.

Top guest favourite
The exterior of the home showcases a white siding and large windows, surrounded by lush greenery. A wooden deck with seating is visible, complemented by stone steps leading to the yard. The fenced area offers a private outdoor space for relaxation.
Cottage in Valparaiso
4.97 out of 5 average rating, 115 reviews

Cozy 2 Bedroom Valparaiso Cottage

This quiet, centrally located north side home offers a perfect place to relax. Only minutes away from downtown Valparaiso and the Indiana Dunes National Park. Conveniently situated for day and evening adventures and activities. Such as, local lakes, parks, and festivals. Enjoy hiking, bird watching, swimming, fishing, fine dining, local breweries and wineries, and so much more.

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