Pet-friendly holiday rentals in West Dundee

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

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.

LakeHome Cozy Retreat! HotTub •FirePit•Bar•Fishing

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

Couples Getaway! Hot Tub, Lake, Fire Pit, Trails

Private entrance to a stunning master suite.A VERY unique property.Sliding suite door opens to screened in pool room. Hot tub all year overlooking my private lake. Pool closed Oct. 1st. Seating area & TV to watch while lounging & swimming. (2) Kayaks 4 you. Walking & bike trails. I am minutes from everything U want. Grill, have a fire in the fireplace&fire pit.Bring your fishing poles! Time 2 RELAX in privacy. When not traveling, I live in main part of home. You won’t see me. No extra guests.

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Huge Pet Friendly East Albany Park Apartment

Enjoy staying in a classic Chicago 2-flat w/vintage charm and modern amenities. This sunny top floor unit has an updated kitchen & bath w/everything you need including in-unit laundry & Central Air. Experience life on the border of 2 great neighborhoods, Albany Park & Ravenswood Manor. Walk to Kedzie & Lawrence for diverse cuisine or walk to Lincoln Square. Take the Kedzie Brown Line to Lakeview & Lincoln Park. $75/pet/per stay. $25/person/night after 2 guests. Check-in/out @11am/@4pm.

Cozy, Comfy, Close to Downtown

Discover serenity in our centrally located guest apartment in our charming St. Charles cottage. The space is pet-friendly with a fenced yard, featuring a spacious kitchen, living room, bath, queen-sized bed, and in-unit laundry. The yard offers views of the Fox River, a peaceful patio, with award-winning parks & biking trails at your doorstep. Note: The unit is studio style located in the lower level of a home. The space is completely private. Only outdoor spaces shared. 😊🪻🏡

Charming Elgin Home with a Great Location

Come enjoy this beautifully restored and charming historic home from the early 1920s. Our place is good for couples, families or for a getaway with friends. Outdoor space with fully fenced backyard. This 2 bed 1 bath has been fully restored and is absolutely adorable! Walking distance to downtown Elgin (less than one mile) and Metra station (only one hour train ride into the city!), and less than 5 minute drive to I-90. Relax and get cozy in this adorable space.

Avondale Cozy 1 Bedroom Attic Apartment 4th FL

Cozy one bedroom attic apartment in Avondale located on top of a 3 story building. Close to Milwaukee, restaurants, and bars. A perfect crash pad for touristing in Chicago. You have your own entrance but since people in this building are working from home, and need to sleep at night, no loud music or partying is allowed at any time! But then, there is no need to bring the party home - you have everything you need just outside the door!

4BR Home w/ Game Room • Ideal for Longer Visits

Looking for a cozy getaway or a comfortable home-away-from-home for a mid-term or extended stay? Welcome to our updated 4-bedroom, 2-bath ranch in Carpentersville—designed for families, work travelers, relocation stays, and anyone needing longer accommodation. Enjoy nearby attractions like Santa’s Village, Paintball Explosion, NOW Arena, and Spring Hill Mall—all within 10 miles or less. Book instantly and secure your stay today!