Places to stay in Freeport

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Top-rated places to stay in Freeport

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

An aerial view captures a sunset over Monroe's historic downtown square. The vibrant sky displays shades of purple and orange, while a bustling street scene is visible below, with shops and buildings surrounding the central Green County Courthouse.

Apartment in Monroe

4.92 out of 5 average rating, 59 reviews

das Baumhaus on Monroe’s Historic Square-2 bedroom

AngieRating, 5 stars2 months ago

After having a host cancel our original rental reservation, I found the listing for das Baumhaus - Dan and Barb's listing, completely last minute!! das Baumhaus was a cozy palace to stay, right on the square in Monroe, WI!! Communication with the property owner was spot on! The location was perfect! New Glarus was just a short drive, and we were able to take in the sights and explore in that area too. The personal touch of finding a bday card on the kitchen counter upon my arrival made my heart melt! Thank you for providing a delightful place to stay for my bday celebration.

Top guest favorite

Home in Mount Carroll

5 out of 5 average rating, 21 reviews

The Main St Place (entire home) Mount Carroll IL

NicoletteRating, 5 stars5 months ago

Nancy and Grant’s place is absolutely adorable! There is such a coziness and charm about the entire house. We could have stayed there for days! It was walking distance to the restaurant that we wanted to go to which was awesome. And our hosts were very great at communicating with us at any time. We will definitely be staying here again! Thank you so much Nancy and Grant!

Guest favorite

A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

4.97 out of 5 average rating, 144 reviews

Private Cozy Cottage Lake Geneva, WI

StefanyRating, 5 stars2 weeks ago

We love staying at Seven Oaks and have many times. I particularly enjoy the soaker tub and we appreciate the cheese tray, drinks, and breakfast foods. It makes it so much more enjoyable to get away and not have to think about running out to get food. We stay as often as we can get away. Such a great place!

Superhost

An indoor swimming pool is showcased, featuring a spacious layout with multiple lanes marked by floating lane dividers. The high, wooden-beamed ceiling allows natural light to filter in. Surrounding the pool, several lounge chairs are positioned for relaxation.

Cabin in Galena

4.88 out of 5 average rating, 126 reviews

Serenity Cabins - A rustic, yet upscale cabin!

SunnyRating, 5 stars6 months ago

I felt super confident in my booking right from the moment I booked it as Dan guided me the entire way and is super amazing at responding and communicating. It was super accomodating when I needed help and it was so reassuring to have a host so kind and responsible.

Top guest favorite

The entrance to the Wide River Winery Inn features a white door framed by a decorative light fixture. A welcoming sign with the text 'Wide River Winery Inn' is mounted on the wall. A potted geranium plant adds a touch of color to the wooden deck.

Apartment in Le Claire

4.93 out of 5 average rating, 308 reviews

Wide River Winery Inn

MonicaRating, 5 stars1 week ago

Our stay was great. Easy for us to find. Communication with Cecilia was easy. Heidi was so fun to talk with and made us feel so welcome. We really enjoyed our stay and plan to come back. The winery was perfect. We enjoyed the brewery and the distillery. Great drinks nice atmosphere. We found breakfast at berries which had great food. It was a nice getaway for the weekend.

Guest favorite

The kitchen sink features a sleek stainless steel design, complemented by a functional drying rack. The granite countertop is accented with a shimmering pattern, and dish soap is visible nearby, ensuring readiness for meal preparation and clean up.

Home in Rockford

4.93 out of 5 average rating, 46 reviews

Clean & bright ranch home. 5 Min to downtown

YolandaRating, 5 stars1 month ago

This Airbnb was spacious, accommodating, and felt like a true home away from home. The host was very attentive and thought of every detail, from the washer and dryer to charging ports on the nightstands. The home has two bedrooms, including a bunk bed and sleeper sofa, and the immaculate gourmet kitchen with stainless steel appliances was a highlight. The master bedroom was spacious and the bed super comfy. The fluffy towels and hot shower with great water pressure added to the comfort. I also appreciated the books to read and board games to play, perfect for relaxation. The quiet neighborhood made for a peaceful stay, and check-in was seamless. I would love to write more, but AirBnB limits you to 1000 characters! Overall, a fantastic experience—I would definitely stay here again! 💯

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Popular amenities for Freeport places to stay

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Freeport's top sights

The Wagner House4 locals recommend

Cub Foods3 locals recommend

Little Cubs Field3 locals recommend

Eilerts Cocktails & Tee Box3 locals recommend

Lincoln Douglas Debate Square3 locals recommend

Cannova's3 locals recommend

Other great vacation rentals in Freeport

Top guest favorite

An aerial view captures the private lakefront property, surrounded by lush greenery. The spacious lawn leads to two docks, set along the calm water. Nearby, pathways and gardens are visible, enhancing the serene lakeside setting.

Home in Freeport

4.98 out of 5 average rating, 177 reviews

Willow Lake Getaway Cozy for 2 - or large families

ChaseRating, 5 stars1 week ago

An amazing place for a weekend get away with friends. Rodger was a great host, always on top of things and answering questions that we had, and going above and beyond to make sure our stay was amazing! The pictures do not do this place justice!

Top guest favorite

A modern kitchen area features sleek cabinetry and stainless steel appliances. The open layout connects to a dining space with a table and chairs. Natural light brightens the room through large windows, complementing the neutral color scheme and decorative elements placed strategically throughout.

Townhouse in Galena

5 out of 5 average rating, 16 reviews

Perfect Getaway: Newly Renovated

CathyRating, 5 stars8 months ago

Julie's place was absolutely beautiful, surrounded by stunning natural scenery. The property was impeccably clean, and Julie was incredibly responsive throughout our stay. The house club pools were a fantastic bonus that added to the overall experience. We will definitely come again!

Top guest favorite

A modern two-story home is presented, featuring a combination of horizontal and vertical siding in shades of green and beige. Large windows are visible on both levels, allowing natural light to enter. A spacious deck with a railing overlooks the front yard and surrounding trees.

Home in Galena

4.98 out of 5 average rating, 62 reviews

Jackson Ready Properties

MariaRating, 5 stars1 month ago

Beautiful house to stay at. Definitely enjoyed the stay. Very relaxing and the view was phenomenal. Hope to come back someday during warmer weather.

Guest favorite

Home in Galena

4.9 out of 5 average rating, 20 reviews

A&D Rise Getaways @ Oak Glen Retreat

IdylRating, 5 stars2 weeks ago

Our stay was perfect! It was a very comfy, clean, cozy townhouse that had everything we needed. We did take advantage of the rec room, which was really fun. The surroundings were beautiful as it was in the middle of nature. The Country store was just a quick car ride away if you didn’t feel like making the trek to town. Danielle was a great host and was very responsive. I would definitely stay here again!

Top guest favorite

A spacious backyard view captures the green expanse of the 9th fairway on the East Golf Course. A modern grill sits in the foreground, with flowering shrubs adding color to the side. A clear sky with scattered clouds extends above the landscape.

Townhouse in Galena

4.93 out of 5 average rating, 100 reviews

Charming golf villa perfect for long or short term

ChrystalRating, 5 stars6 days ago

This place was great, about 10-15 mins from downtown galena, with a nice scenic drive to take up the time with beautiful hills and pastures. Quiet neighborhood. Mattress could be less firm or covered with a soft mattress topper, but that’s just preference. The place was very clean and well maintained. Angie was informative. Would stay again, for sure!

Guest favorite

A spacious villa is set against a backdrop of rolling hills and cloudy skies. The exterior features a blend of wood and grey siding, with a welcoming porch that extends around the lower level. Chickens can be seen freely roaming on the lush green lawn.

Villa in Benton

5 out of 5 average rating, 12 reviews

The stay with the story

DemetrioRating, 5 stars2 months ago

Great people. We had a swift check-in and were welcomed by a beautiful space that provides absolute privacy. Could have been better if it was warm so you can enjoy the enormous space around the property. Can be suitable for retreats, intimate wedding venue.

Top guest favorite

Home in Lake Geneva

4.96 out of 5 average rating, 81 reviews

Sleeps 12, 5 bedroom, 2 living rooms and game room

RachelRating, 5 stars1 week ago

This home was incredible for a weekend away with girlfriends. We loved the views of lake como m, the proximity to downtown lake Geneva, and how well stocked the house was with all the essentials and more (especially in the kitchen!). Only regret was not making our stay a full week long trip!

Top guest favorite