
House holiday rentals in Westchester
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Top-rated house rentals in Westchester
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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

Steps from the beach and a mile from National Park
Perfect for family or friends to relax and enjoy Indiana’s Dunes National Park! The Holliday House is a 2022 custom built home with lake views and a beach path just STEPS from the front door! This 2000 sq ft open concept design features 3 bedrooms and 3 bathrooms, 16’ ceilings, open great room with beautiful indoor/outdoor kitchen, custom dining seating for 8, and loft hammock. Hosts live next door and are easily available if needed! Everything is on the 1st floor except for the 3rd bedroom.

Red River Cottage w/firepit, Blackhawk on the Fox!
Summertime in 3, 2, 1.... Hello Airbnb folks! Come visit our wonderful riverfront cottage, ready and waiting. A two bedroom 750 sqft house with 1 bathroom on just under an acre property. A special place to relax, do some fishing, grilling, and roasting marshmallows on the fire. Located in a secluded unincorporated Fox River neighborhood in Kane County just a half mile from Blackhawk waterfall via bike path. The subdivision is hidden between the Jon J. Duerr and Blackhawk forest preserves.

Home in Glen Ellyn
Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

RetroModern Bungalow | free parking | pet friendly
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four 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.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Lockports Famous Hideaway ~ 2bdrm Guest House Flat
A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! *Note: Pricing is based on "Double Occupancy". Can accommodate up to 6 guests. Extra charges per person apply after 2 guests.

SW Evanston Private, Stylish, Spacious Suite
Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

Elmhurst NEW - Super Clean Modern Farmhouse!
Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Games, Grounds, Goodness in DG
Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

Jacuzzi, King Beds, Easy Access to DT Chicago!
Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs, a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!

Big 5BR 3.5BA Game Rm Prime Location minutes to DT
Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.
Popular amenities for house rentals in Westchester
House rentals with a pool

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Elegant Executive Residence with Hottub

Pool & Beach Haven-private pool, steps to beach!

Chic Fulton Market Oasis + Curated Comfort & Style

Munster hide away

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ

The Fox River Farmhouse-walk to downtown and pool

Backyard Paradise/ Private Pool + Peaceful Stay
Weekly house rentals

The Gallery, King, Queen, Sofa Bed, smart TV’s

Fun and Cozy Family Home Near O’hare Airport

Cozy Home near O'Hare & fun Hubs

Elegant 4bedroom, 5 bathroom home on a great block

Bliss in Brookfield- 5BR, 3BA, Fenced Yard

A Comfortable Stay While You are Away in Oak Park

Near city 5 BR, 2bath, 2 living room private home

Grand Retreat/5Brs/Game Room
Private house rentals

Lakefront View Getaway Home! Hot tub! Kayak!

Villa Park Getaway – Cozy 3BR Retreat Near Chicago

The Westmore Retreat

Peaceful Bolingbrook Getaway

Cozy 2 bedroom home in a wonderful neighborhood.

Private Apartment • Ground Floor • Free Parking

At the center of it all, a secret suburban gem!

Cozy Ranch w/ King Bed & 3 Baths – Great Location!
Destinations to explore
- Chicago Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Louisville Holiday rentals
- Detroit Holiday rentals
- Southern Indiana Holiday rentals
- Columbus Holiday rentals
- St. Louis Holiday rentals
- Cincinnati Holiday rentals
- Wisconsin River Holiday rentals
- Milwaukee Holiday rentals
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Illinois Beach State Park
- Willis Tower
- Indiana Dunes State Park





