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House vacation rentals in Homewood

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Top-rated house rentals in Homewood

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Home

4.87 out of 5 average rating, 127 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Home

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Home

4.91 out of 5 average rating, 118 reviews

Downtown Chesterton "Grant-Cottage"

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

Home

4.85 out of 5 average rating, 13 reviews

Enamored in Elmhurst

Have fun with the whole family at this beautifully renovated house with and open floor plan, fully stocked kitchen, 4 bedrooms, 2 bathrooms with smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home is located only minutes from the highways, enjoy the deck right off the living room and overlooking a private yard . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a theater room with a sectional sleeper sofa if more space is needed.

Home

4.91 out of 5 average rating, 173 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Home

4.87 out of 5 average rating, 38 reviews

The Waverly Retreat

Located an easy 1.6 miles to Indiana Dunes State Park, 2 miles South of Porter Beach, not even a mile from the South Shore train station with direct access to downtown Chicago, and 2 miles from the historic downtown Chesterton, this house has access to everything you could ask for. Not only is the location perfect if you want a relaxing weekend at the beach or some active hiking days on the many miles of trails, but the house itself is cozy and convenient with all the comforts of home.

Home

4.8 out of 5 average rating, 20 reviews

Modern Boho Beach House with Hot Tub

We invite you to come stay at our Miller Lake house, where luxury meets nature. After spending the day at West Beach National Park hiking, swimming and picnicking or shopping downtown Miller on Lake Street, the relaxing elements of this modern boho lake house invite you to stay. Feel free to chill at the bar, grill out on the porch, watch a movie on the 75" home theater or open the sliding door to the 7 person Hot Springs jacuzzi open year round! Your perfect vacation starts here!

Home

4.91 out of 5 average rating, 118 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Home

4.94 out of 5 average rating, 62 reviews

Party Porch Place in Miller Beach, Indiana Dunes

Just 400 feet from the most beautiful beach Lake Michigan has to offer! Enjoy the peaceful lakefront, hiking and exploring the Indiana Dunes National Park, or stay in at the home's 'party porch' watching movies outside on our patio projector while enjoying the yard and fire pit. Fully fenced backyard. This home has comfortable surroundings and a family friendly laid back vibe-- we want you to feel like you are staying at your family beach home. We provide beach necessities

Home

4.92 out of 5 average rating, 60 reviews

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Home

4.93 out of 5 average rating, 134 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

Home

4.96 out of 5 average rating, 164 reviews

•Serene riverfront bungalow next to parks + kayaks

3 bedroom house with gorgeous views of the Kankakee River. The house sits on the river adjacent to Conrad Park and steps away from the Island Park. Enjoy watching the wildlife & the river from the large deck or from the patio near the bank. Completely renovated house with all the amenities of home. Walk to local restaurants and shops. Conveniently located 50 miles from downtown Chicago. Need extra space, book the house right next door, too!

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Popular amenities for Homewood house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home

4.91 out of 5 average rating, 141 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Home

4.92 out of 5 average rating, 37 reviews

Cozy house in Schererville

Home

5 out of 5 average rating, 9 reviews

Munster hide away

Home

4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

Home

4.95 out of 5 average rating, 40 reviews

Whole House with a Hot Tub!

Home

4.81 out of 5 average rating, 226 reviews

Oasis , Near Beach, Hard Rock and Dunes

Home

4.93 out of 5 average rating, 75 reviews

Beautiful Spanish style Home (w/inground pool)

Home

4.84 out of 5 average rating, 82 reviews

Beautiful Home Oasis

Weekly house rentals

Home

4.95 out of 5 average rating, 125 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

Home

4.93 out of 5 average rating, 264 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Home

4.98 out of 5 average rating, 43 reviews

Suburban Serenity~Grill, Fire pit, Big yard~

Home

4.83 out of 5 average rating, 144 reviews

The Spa of Downtown Whiting

Home

4.94 out of 5 average rating, 181 reviews

Wrigleyville Greystone

Home

4.94 out of 5 average rating, 220 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

Home

5 out of 5 average rating, 49 reviews

RANCH, House-tel: updated full kitchen, comfy beds

Home

4.87 out of 5 average rating, 127 reviews

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Private house rentals

Home

4.76 out of 5 average rating, 37 reviews

Comfortable 4 bedroom home with indoor fireplace

Home

4.94 out of 5 average rating, 16 reviews

Warm bungalow in New City

Home

4.88 out of 5 average rating, 126 reviews

Home away from home

Home

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Home

4.88 out of 5 average rating, 48 reviews

Grand Victorian Mansion in Austin Area

Home

4.81 out of 5 average rating, 183 reviews

Warm and comfortable inviting Suburban home !

Home

4.8 out of 5 average rating, 5 reviews

Home Sweet Home

Home

4.94 out of 5 average rating, 109 reviews

Quiet cul-de-sac with huge fenced in backyard

Quick stats about house rentals in Homewood

Total rentals
30 properties
Nightly prices starting at
€ 48 before taxes and fees
Total number of reviews
680 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore