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Port Barrington Holiday Rentals

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Our top choices for Port Barrington holiday rentals

1. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is NZ$336
includes taxes & fees
3 Sept - 4 Sept
Little Fox Cottage - A Cozy Riverview Getaway

2. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is NZ$757
includes taxes & fees
3 Sept - 4 Sept
King bed Crystal Lake Mchenry Cary Cozy

3. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
8.0 out of 10, Very good, (1 review)
"Conveniently located near restaurants and downtown. Apartment was clean. Nicely decorated. Cute coffee station. Big table in dining area."
United States
Kim B.
The price is NZ$583
includes taxes & fees
2 Sept - 3 Sept
Spacious 3 Bedroom

4. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is NZ$586
includes taxes & fees
8 Sept - 9 Sept
Quaint Bungalow, near Great Lakes Naval Base

5. This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!
fox lake
9.8 out of 10, Exceptional, (30 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is NZ$496
includes taxes & fees
3 Sept - 4 Sept
This is a VACATION spot with a million dollar view!

6. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.4 out of 10, Very good, (11 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is NZ$498
includes taxes & fees
1 Sept - 2 Sept
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

7. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
The price is NZ$1,140
includes taxes & fees
21 Sept - 22 Sept
Waterfront - Private Dock - Two Suites

8. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
10.0 out of 10, Exceptional, (14 reviews)
"Everything nice neat and clean"
United States
Anonymous traveller
The price is NZ$185
includes taxes & fees
6 Sept - 7 Sept
1 King Bed | Non-Smoking, Kitchen

9. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is NZ$448
includes taxes & fees
1 Sept - 2 Sept
The Tailor House

10. 124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is NZ$386
includes taxes & fees
1 Sept - 2 Sept
124 Lofts #1 - Downtown Dundee - Walk to Dining

11. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Always a pleasure to stay here when visiting my son!"
United States
Jen C.
The price is NZ$446
includes taxes & fees
1 Sept - 2 Sept
Kildahl House - Boutique Farmhouse Suite #2

12. 124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (28 reviews)
"Lovely stay! Great location!"
United States
David K.
The price is NZ$386
includes taxes & fees
1 Sept - 2 Sept
124 Lofts #3 - Downtown Dundee - Walk to Dining

13. HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
McHenry
9.2 out of 10, Wonderful, (46 reviews)
"We stayed with our wedding bridal party here, and this massive and beautiful house was the perfect location to spend the weekend with all of our best friends! The house is obviously gorgeous, and the pool, hot tub, fire pit and pool table added an extra tier of fun. We hosted our rehearsal dinner on the back lawn and rented tables and chairs through the property, which was incredibly convenient.The property managers were communicative and very helpful throughout the process. I highly...
United States
Brittany B.
The price is NZ$2,315
includes taxes & fees
1 Sept - 2 Sept
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

14. The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is NZ$460
includes taxes & fees
1 Sept - 2 Sept
The Main Event Game House on the Huntley Square!

15. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (86 reviews)
"Lovely, quiet property with easy access to retail & restaurants. Perfect for a long weekend away."
United States
Suzanne H.
The price is NZ$360
includes taxes & fees
13 Sept - 14 Sept
Master qtr close to nature & easy urban facilities

16. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (17 reviews)
"This is a lovely place to call “home base” while visiting Chicago and surrounding communities. Comfortable, clean, quiet and nicely decorated. My little dogs even had a welcome basket! I wish I could have stayed a bit longer"
United States
Thea
The price is NZ$407
includes taxes & fees
23 Sept - 24 Sept
Kildahl House - Boutique Farmhouse Suite #1

17. Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard
Libertyville
Family Stay with Game Garage, Fire Pit, Streaming TVs and Private Yard

18. Lovely 1-bedroom apartment with AC in charming Woodstock

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.0 out of 10, Very good, (2 reviews)
"Cute little apartment over the top of a boba shop. There is a little hidden bedroom with a twin bed on the other side of the living room that was so cozy. In the bedroom there is a King size bed with a very comfortable mattress and plenty of closet space. The bathroom is small but easy to use, and the kitchen is large and roomy. We didn’t get to spend much time at the place but we enjoyed the location and the quiet neighborhood. On site workers were also so helpful when we needed an extension...
United States
Callie C.
The price is NZ$305
includes taxes & fees
1 Sept - 2 Sept
Lovely 1-bedroom apartment with AC in charming Woodstock

19. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake Elegance: Serene 2BR Townhome Retreat
Wonder Lake
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
The price is NZ$656
includes taxes & fees
14 Sept - 15 Sept
Wonder Lake Elegance: Serene 2BR Townhome Retreat

20. Recharge in This Charming 1BR Apt

Recharge in This Charming 1BR Apt
Arlington Heights
8.0 out of 10, Very good, (3 reviews)
"Nice for the price. Excellent location."
United States
Al E.
The price is NZ$430
includes taxes & fees
2 Sept - 3 Sept
Recharge in This Charming 1BR Apt
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 Port Barrington Hotel Reviews

Find out more about Port Barrington

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Port Barrington holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Port Barrington. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Port Barrington. Seeing all the best attractions is bound to make you fall in love with Port Barrington. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Port Barrington short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Port Barrington?

Yes, there are holiday rentals close to the most popular sights in Port Barrington, or you can select a more secluded option if you're looking for a relaxing stay. Port Barrington is known for its parks.

What are some of the best holiday rentals that Port Barrington has to offer?

Pleasant 3-bedroom house with occupied basement separate entrance.: This holiday home rental outside of Port Barrington has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Port Barrington?

While exploring the area, visit family-friendly sights like Six Flags Great America, or get outside and enjoy nature at Fox River Preserve. In the wider area, you’ll find Moraine Hills State Park and Three Oaks Recreation Area.

What are holiday rentals like in Port Barrington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Port Barrington. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family trip.