Floating stationary houseboat on river!
Floating stationary houseboat on river!
Floating stationary houseboat on river!
Floating stationary houseboat on river!
Floating stationary houseboat on river!

Floating stationary houseboat on river!

3 bedrooms·2 baths
East Dubuque • Illinois
4.9(107 reviews)
$295 – $425/ night(excl. fees & taxes)
Floating River cabin- HOT TUB!
Floating River cabin- HOT TUB!
Floating River cabin- HOT TUB!
Floating River cabin- HOT TUB!
Floating River cabin- HOT TUB!

Floating River cabin- HOT TUB!

3 bedrooms·1 bath
East Dubuque • Illinois
4.95(150 reviews)

$1,089.16 USD total for 3 nights

Mar 1 – 4, 2027

New green paint color! The Snug Owl is a dog friendly 400 sq ft tiny home on its own city lot located in a quiet neighborhood just 7.7 miles from Starved Rock State Park. Suitable for 2 adults and up to 2 dogs. No cats, please.
The Snug Owl view from the entry door. The entire tiny home is 20 ft by 20 ft and is the perfect size for 2 humans and 2 dogs who want to hike nearby Starved Rock and Matthiessen State Parks.
The Snug Owl has a steel fire pit for relaxing after hiking, eagle watching, antiquing, and wine tasting. A small bundle of firewood is provided at no charge.
Queen Stearns & Foster bed with a firm mattress in the sleep area. Cool weather bedding includes cotton sheets and a warm duvet with extra blankets. Each side of the bed has a nightstand and power outlets.
Light and bright kitchen in shades of cream and gray with stainless steel accents and appliances. Coffee is provided for the drip coffeemaker and there is an electric water kettle for tea.

Snug Owl Cottage - Starved Rock Dog Friendly Home

1 bedroom·1 bath
La Salle • Illinois
5(350 reviews)

$425.08 USD total for 3 nights

Nov 15 – 18, 2026

Outdoor patio and hot tub.
Master bed with smart tv, fireplace, king bed, and walk in closet.
Full kitchen, including a dishwasher.
Stunning sunsets at the marina.
Wow! Unique floating cabin! HOT TUB!

Wow! Unique floating cabin! HOT TUB!

2 bedrooms·1 bath
East Dubuque • Illinois
5(8 reviews)

$1,462.44 USD total for 3 nights

Apr 1 – 4, 2027

Spanish Style Villa in the heart of Rockford
Walk into a cozy living room
Television featuring Netflix, Hulu and Amazon Prime available inside the armoire
Experience another world inside the backyard cantina
Enjoy the private hot tub with a nearby sitting area

Hidden Gem Spanish Style Villa

4 bedrooms·3 baths
Rockford • Illinois
4.98(313 reviews)

$1,032.00 USD total for 3 nights

Nov 22 – 25, 2026

* Traveler's Sanctuary 2 br/2ba, unit sf-home
* Traveler's Sanctuary 2 br/2ba, unit sf-home
* Traveler's Sanctuary 2 br/2ba, unit sf-home
* Traveler's Sanctuary 2 br/2ba, unit sf-home
* Traveler's Sanctuary 2 br/2ba, unit sf-home

* Traveler's Sanctuary 2 br/2ba, unit sf-home

2 bedrooms·2 baths
Roscoe • Illinois
4.99(322 reviews)

$545.40 USD total for 3 nights

Nov 13 – 16, 2026

Studio #2 w/Waterfront view-HOT TUB-massage chair image 1
Studio #2 w/Waterfront view-HOT TUB-massage chair image 2
Studio #2 w/Waterfront view-HOT TUB-massage chair image 3
Studio #2 w/Waterfront view-HOT TUB-massage chair image 4
Studio #2 w/Waterfront view-HOT TUB-massage chair image 5

Studio #2 w/Waterfront view-HOT TUB-massage chair

1 bedroom·1 bath
East Dubuque • Illinois
5(4 reviews)

$807.52 USD $661.01 USD total for 3 nights

Nov 7 – 10, 2026

The porch is a comfortable place to relax and enjoy the view.
Peaceful, cozy cabin
All seasons are gorgeous here, but there's something so inviting about a cabin in the snow.
Fully appointed kitchen with beautiful cabinets.
The breakfast bar adds extra seating for meals without taking up space in the cabin.

Lazy Oak Retreat

2 bedrooms·1 bath
Jerseyville • Illinois
4.96(208 reviews)

$450.00 USD total for 3 nights

Nov 10 – 13, 2026

2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village
2BD/1 BA with summer patio in quiet Roscoe Village

2BD/1 BA with summer patio in quiet Roscoe Village

2 bedrooms·1 bath
Chicago • Illinois
4.97(98 reviews)

$491.73 USD total for 3 nights

Nov 9 – 12, 2026

Space for relaxing and a table for everyone
Gourmet chef's kitchen & space for all!
Beautiful space for family vacation, girls getaways
MFL 2 West
MFL 2 West

MFL 2 West

3 bedrooms·2 baths
Chicago • Illinois
4.95(206 reviews)

$2,662.02 USD $2,262.71 USD total for 3 nights

Nov 16 – 19, 2026

What a view from my 13th floor!
Stately building entrance
Gallery Hallway looking towards Living Room
Spacious living room
My view of Jackson Harbor and partial Chicago skyline.

Art Collector's Pied-à-terre

2 bedrooms·2 baths
Chicago • Illinois
4.84(247 reviews)

$2,980.00 USD total for 32 nights

Nov 6 – Dec 8, 2026

Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number
Chicago 2BR Condo- King Sleep Number

Chicago 2BR Condo- King Sleep Number

2 bedrooms·1 bath
Elmwood Park • Illinois
4.63(8 reviews)

$1,200.00 USD $1,095.00 USD total for 7 nights

Nov 6 – 13, 2026

Main Floor
Master Bedroom 2nd floor
Dining area
1500Main EVANSTON
Main Floor

1500Main EVANSTON

2 bedrooms·1½ baths
Evanston • Illinois
5(166 reviews)

$1,140.42 USD total for 4 nights

Nov 16 – 20, 2026

Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta
Stunning Lake house on peaceful Sta

Stunning Lake house on peaceful Sta

5 bedrooms·2½ baths
Ingleside • Illinois
4.86(22 reviews)

$2,256.65 USD total for 5 nights

Nov 6 – 11, 2026

Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly
Chicago 2Br 90s Condo - Very Kid Friendly

Chicago 2Br 90s Condo - Very Kid Friendly

2 bedrooms·1 bath
Elmwood Park • Illinois
4.5(4 reviews)

$30,120.00 USD $18,120.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access
Chicago 2Br Condo -Nature Themed Downtown Access

Chicago 2Br Condo -Nature Themed Downtown Access

2 bedrooms·1 bath
Elmwood Park • Illinois
5(2 reviews)

$30,150.00 USD $25,650.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Charming ranch home with vibrant fall views and glowing sunset curb appeal
*King bed *Outdoor Living *Sought-After Area
*King bed *Outdoor Living *Sought-After Area
Charming backyard lounge with cozy deck seating and private garden vibe
Cozy boho lounge with greenery, armchairs, and warm natural accents

*King bed *Outdoor Living *Sought-After Area

3 bedrooms·1½ baths
Northbrook • Illinois
5(135 reviews)

$1,492.00 USD total for 3 nights

Nov 19 – 22, 2026

Beautifully home with 5 bedrooms image 1
LIving Room
Kitchen
Dining Table
Beautifully home with 5 bedrooms image 5

Beautiful home with 5 bedrooms

5 bedrooms·2 baths
Rockford • Illinois
4.95(56 reviews)

$1,212.75 USD total for 3 nights

Nov 6 – 9, 2026

Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access
Chicago 2Br Condo - Downtown Access

Chicago 2Br Condo - Downtown Access

2 bedrooms·1 bath
Elmwood Park • Illinois
5(3 reviews)

$30,150.00 USD $25,650.00 USD total for 30 nights

Nov 6 – Dec 6, 2026

Cute Cottage on the Bay
Cute Cottage on the Bay
Cute Cottage on the Bay
Cute Cottage on the Bay
Cute Cottage on the Bay

Cute Cottage on the Bay

2 bedrooms·1 bath
New Boston • Illinois
4.91(32 reviews)

$478.06 USD total for 3 nights

Nov 8 – 11, 2026

Step into serenity at our welcoming retreat. Follow detailed check-in directions to unlock the smart lock for secure access. Relax in the cozy living room with a 30" Smart TV and a collection of board games. Outside, unwind in the serene backyard.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.
Unwind in our inviting sanctuary. Seamless check-in with detailed instructions and a smart lock. Cozy up in the relaxing living room, equipped with a 30" Smart TV and a selection of board games. Step outside to a tranquil backyard with a pergola.
Step into tranquility with seamless check-in and a smart lock. Explore local treasures with our custom guidebook. Outside, unwind in the serene backyard oasis, complete with a pergola, fire-pit, outdoor gas grill, and picnic table dining.
Discover local gems in our custom guidebook. Outside, find tranquility in the serene backyard oasis. Entertain in the lower-level living room, complete with a 55" Smart TV, kitchenette, and study desk. The sofa can also be used for sleeping space.

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bedrooms·2½ baths
Chicago • Illinois
4.9(106 reviews)

$1,465.00 USD total for 3 nights

Nov 6 – 9, 2026

Hyde Park 2BR UChicago Medical Museums 20% OFF
Main Bedroom
Hyde Park 2BR UChicago Medical Museums 20% OFF
Hyde Park 2BR UChicago Medical Museums 20% OFF
Quick view of upstairs "half kitchen," middle of tile restoral. NOTE there is a microwave and induction burner, NO STOVE.

Hyde Park 2BR UChicago Medical Museums 20% OFF

2 bedrooms·1 bath
Chicago • Illinois
5(4 reviews)
$233/ night(excl. fees & taxes)
Spacious open 4 bedroom vacation rental loft
MFL 2 East
MFL 2 East
Skyline views
Brick & timber loft with full hight walls for privacy

MFL 2 East

4 bedrooms·3 baths
Chicago • Illinois
4.93(120 reviews)

$2,113.34 USD $1,827.39 USD total for 3 nights

Nov 9 – 12, 2026

Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop
Modern Western Logan Square Flat Healy Metra Stop

Modern Western Logan Square Flat Healy Metra Stop

2 bedrooms·1 bath
Chicago • Illinois
4.75(24 reviews)

$492.26 USD total for 3 nights

Nov 6 – 9, 2026