Holiday rentals in Freeport

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Freeport

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Loft in Monroe

4.99 out of 5 average rating, 121 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

22–29 Jan

$151 SGD per night
Guest favourite

Cabin in Oregon

4.97 out of 5 average rating, 130 reviews

The Corner Cabin

The cabin has a view of the peaceful Rock River. Very relaxing & cozy. Minutes from Castle Rock State Park. Enjoy canoeing, fishing, & hiking trails. Reconnect with nature, play a board game, barbecue, watch the birds & engage in outdoor activities. Enjoy exploring the quaint small towns, antiquing, & local restaurants. Go from city life to country life, just “90” minutes from Chicago. This is a great place to relax & unwind. Due to location & your carrier you must be patient with our WiFi.

20–27 Nov

$151 SGD per night
Guest favourite

Home in Freeport

4.98 out of 5 average rating, 137 reviews

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

5–12 Dec

$410 SGD per night

Popular amenities for Freeport holiday rentals

Stay near Freeport's top sights

Walmart Supercenter3 locals recommend
Krape Park7 locals recommend
Union Dairy4 locals recommend

Other great holiday rentals in Freeport

Guest favourite

Flat in Albany

4.93 out of 5 average rating, 158 reviews

Sugar River Hideaway

21–28 Oct

$154 SGD per night
Guest favourite

Chalet in Elizabeth

4.91 out of 5 average rating, 288 reviews

Galena Country Getaway

27 Feb – 6 Mar

$173 SGD per night
Guest favourite

Home in Gratiot

4.99 out of 5 average rating, 200 reviews

The Old Farmhouse

16–23 Jan

$155 SGD per night
Guest favourite

Flat in Monroe

4.99 out of 5 average rating, 171 reviews

MJ's Penthouse ( A piece of paradise in Monroe)

30 Jun – 7 Jul

$278 SGD per night
Guest favourite

Guest suite in Stoughton

4.92 out of 5 average rating, 169 reviews

Guest suite w/ Private Entrance & Outdoor Fire pit

30 Jan – 6 Feb

$126 SGD per night
Guest favourite

Guest house in Mineral Point

4.94 out of 5 average rating, 174 reviews

Lumber Yard Cottage, a cozy retreat

15–22 Feb

$131 SGD per night
Guest favourite

Guest suite in Freeport

5.0 out of 5 average rating, 81 reviews

Private Lower Level Suite in Home-Sep Entrance!

21–28 Feb

$185 SGD per night
Guest favourite

Flat in Freeport

4.98 out of 5 average rating, 42 reviews

Downtown Freeport! Walking distance to everything.

12–19 Jun

$70 SGD per night
Guest favourite

Home in Davis

4.81 out of 5 average rating, 43 reviews

A little bit rustic and retro fun 3 bedroom home

23–30 Sep

$158 SGD per night
Guest favourite

Home in Lanark

4.91 out of 5 average rating, 45 reviews

Country charm + newly renovated 3bd / 1.5 ba

22–29 Apr

$149 SGD per night
Guest favourite

Flat in Stockton

5.0 out of 5 average rating, 25 reviews

Charming Upstairs 2 Bdrm

29 Jul – 5 Aug

$125 SGD per night
Guest favourite

Home in Winslow

4.97 out of 5 average rating, 37 reviews

Winslow House-your home away from home

24–31 Mar

$233 SGD per night

Destinations to explore

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  4. Stephenson County
  5. Freeport