Holiday rentals in Freeport
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Top-rated holiday rentals in Freeport
Guests agree: these stays are highly rated for location, cleanliness and more.
Loft in Monroe
4.99 out of 5 average rating, 121 reviewsLoft 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
Cabin in Oregon
4.97 out of 5 average rating, 130 reviewsThe 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
Home in Freeport
4.98 out of 5 average rating, 137 reviewsWillow 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
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Freeport holiday rentals
Other great holiday rentals in Freeport
Flat in Albany
4.93 out of 5 average rating, 158 reviewsSugar River Hideaway
21–28 Oct
Chalet in Elizabeth
4.91 out of 5 average rating, 288 reviewsGalena Country Getaway
27 Feb – 6 Mar
Home in Gratiot
4.99 out of 5 average rating, 200 reviewsThe Old Farmhouse
16–23 Jan
Flat in Monroe
4.99 out of 5 average rating, 171 reviewsMJ's Penthouse ( A piece of paradise in Monroe)
30 Jun – 7 Jul
Guest suite in Stoughton
4.92 out of 5 average rating, 169 reviewsGuest suite w/ Private Entrance & Outdoor Fire pit
30 Jan – 6 Feb
Guest house in Mineral Point
4.94 out of 5 average rating, 174 reviewsLumber Yard Cottage, a cozy retreat
15–22 Feb
Guest suite in Freeport
5.0 out of 5 average rating, 81 reviewsPrivate Lower Level Suite in Home-Sep Entrance!
21–28 Feb
Flat in Freeport
4.98 out of 5 average rating, 42 reviewsDowntown Freeport! Walking distance to everything.
12–19 Jun
Home in Davis
4.81 out of 5 average rating, 43 reviewsA little bit rustic and retro fun 3 bedroom home
23–30 Sep
Home in Lanark
4.91 out of 5 average rating, 45 reviewsCountry charm + newly renovated 3bd / 1.5 ba
22–29 Apr
Flat in Stockton
5.0 out of 5 average rating, 25 reviewsCharming Upstairs 2 Bdrm
29 Jul – 5 Aug
Home in Winslow
4.97 out of 5 average rating, 37 reviewsWinslow House-your home away from home
24–31 Mar
Destinations to explore
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