Dolton Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Dolton vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1009)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
United States
Deidre
The price is ￥18,314
￥26,047 total
includes taxes & fees
Dec 21 - Dec 22
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (401)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (650)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

Kasa South Loop Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (389)
"Great apartment, great view, close to good amenities, very safe."
United Kingdom
Ian
Kasa South Loop Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Do not book. This is a scam you will be asking to zelle a several hundred dollar security deposit after paying in full and before check in. You’ll receive sketchy FaceTime audio calls and messages from several different numbers requesting this. "
United States
Brooke
The price is ￥16,322
￥19,161 total
includes taxes & fees
Dec 18 - Dec 19
Chicago luxury home suites
Property entrance
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy
4.0 star property
Near West Side
9.6 out of 10, Exceptional, (225)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
4.0 out of 10, (68)
"Good "
United States
Abel
The price is ￥13,114
￥14,817 total
includes taxes & fees
Dec 17 - Dec 18
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO
West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥12,309
￥31,508 total
includes taxes & fees
Dec 18 - Dec 19
Twice as Nice: Chic 2BR Stay with Style & Space
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown
2.0 star property
Bridgeport
Stylish Apartment near Chicago Downtown
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Near West Side
10.0 out of 10, Exceptional, (270)
"Wonderful place, great location! Communication was easy and everything met and exceeded our expectations."
United States
Kathleen N.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
TV, offices
Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (7)
"Great place. Very comfortable & really nice location- loved the corner coffee shop "
United States
Sandra
Modern West Loop Gem-City Views & Prime Location 6
Interior
Art Villa

Art Villa

Art Villa
5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
Art Villa
Dining
55-56 Mag Mile Penthouse

55-56 Mag Mile Penthouse

55-56 Mag Mile Penthouse
Downtown Chicago
10.0 out of 10, Exceptional, (300)
"Great location, great property, great views. "
United States
Mark D.
55-56 Mag Mile Penthouse
Interior
Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!
East Garfield Park
7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!
2 bedrooms, WiFi, wheelchair access
Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi

Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Blue Island
7.6 out of 10, Good, (4)
"Only issue was the water pressure in the bathroom was very very low. "
United States
Derrick M.
The price is ￥22,879
￥53,331 total
includes taxes & fees
Dec 20 - Dec 21
Charming 2-bedroom apartment in marvelous Blue Island with WiFi
Interior
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Near North Side
9.4 out of 10, Exceptional, (106)
"The space was good for our gathering. We could spread out and accommodate different needs - early risers, late risers, bed hogs, loud breathers :) the location was great for us. The location was great for us. "
United States
Elaine W.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Fridge, microwave, oven, stovetop
Experience Chicago living near United Center

Experience Chicago living near United Center

Experience Chicago living near United Center
Austin
9.2 out of 10, Wonderful, (29)
"We were in town with our rowing team for a regatta, and this was a perfect spot to stay! Amenities were perfect for our needs, the living room is super spacious for some morning yoga, and the owners were responsive to any questions we had. Will definitely be saving this location for our trip here next year?"
United States
McKenzie J.
Experience Chicago living near United Center
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is ￥9,766
￥26,116 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Stylish 1BR in West Loop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dolton Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"The staff was so friendly and helpful and the hotel was beautiful"
Julianne 2-night trip
Posted 10 hours ago
Palmer House a Hilton Hotel

Find out more about Dolton

Search for holiday rentals in Dolton on Expedia! You can easily find your home rentals, villas, holiday apartments in Dolton using one of the methods below:

  • View our selection of featured holiday rentals in Dolton
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  • Enter your travel dates to view the best deals on holiday rentals in Dolton while they last

Look no further and take a look at our great range of rental properties in Dolton!

Frequently asked questions

Are there vacation rentals in Dolton?

Yes, we offer vacation rentals near the most popular attractions in Dolton, or you can go with a secluded option if you want a relaxing place to stay. Dolton is known for its live music and waterfront.

What's the top vacation rental in Dolton?

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: This vacation home rental near Dolton is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of games.

What’s there to see and do in Dolton?

Explore the area and cultural attractions such as Midwest Carvers Museum, or visit a family-friendly sight such as Childrens Museum of Oak Lawn. Soldier Field and River Oaks Center are a couple of places you'll find in the larger area.

What’s a vacation rental in Dolton like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Dolton. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for small groups.