Holiday rentals in Caledonia

4.96 out of 5 average rating, 240 reviews

Cottage in Rockton

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

4.94 out of 5 average rating, 128 reviews

Loft in Rockford

Franklin's Urban Retreat in the heart of downtown

Live the urban city life in this centrally located loft designed with tons of local art and custom built furnishings. Our loft of is an open floor plan with tall exposed ceilings and brick. Have fun playing our full size retro Arcade and slot machine. And when ready to sleep, you are gonna LOVE the Saatva mattress. Located right in the middle of all the downtown action surrounded by the best restaurants and activities. Located above Abreo Restaurant, all guests receive 10% discount during stay

4.88 out of 5 average rating, 129 reviews

Farm stay in Caledonia

Country Guesthouse at Wind Ridge Herb Farm

Welcome to Wind Ridge Herb Farm. Enjoy the peace and tranquility of this beautiful historic, Victorian farm. Just minutes from Rockford, Machesney Park and Beloit, the guesthouse is ideal for couples, friends, families or professionals seeking safe, private and quiet accommodations. Conveniently located near I90, Pierce Lake and Rock Cut State Park, great golf courses and biking, restaurants and shopping, Anderson Japanese Gardens, Nicholas Conservatory and Hard Rock Casino are all nearby.

4.99 out of 5 average rating, 304 reviews

Home in Roscoe

* Travelers Sanctuary 2bed 2bath unit-sf home

Two bedroom, two bath entire first-floor of a single family home. 1350 sq ft. Self check-in. Central Air. Parking in driveway. Host lives in lower unit, separate entrance. 1-acre, wooded backyard. 4 mi to I90/39-Exit Rockton Rd. 11 mi N of Rockford 7-8 minute drive to forest preserves, grocery. Ideal for biz class guests, couples. Safety issues for children under 8 years. Share a bit about yourself, why in the area, who you are traveling with & that you read & agree to "House Rules".

4.95 out of 5 average rating, 191 reviews

Home in Harvard

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Farm stay in Cherry Valley

4.97 out of 5 average rating, 364 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Place to stay in Brodhead

4.97 out of 5 average rating, 158 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Superhost

4.83 out of 5 average rating, 165 reviews

Spacious Cabin-style home w/ Gameroom + Gym!

Welcome to our spacious, yet cozy cabin-style retreat, perfect for both relaxation & entertainment! Enjoy the large yet inviting living room, savor homemade meals in our fully-equipped kitchen, complete with modern appliances. Unleash your inner gamer in our epic Game Room or let the kids explore a world of fun in the dedicated play area. Stay fit on-the-go in our well-equipped home gym, stocked with top-notch equipment. Need to work? Enjoy our dedicated workstation for seamless focus.

4.96 out of 5 average rating, 125 reviews

Flat in Edgewater

Upscale Urban Retreat 1 Bedroom Apt. 2nd floor

Charm Art Style. Hardwood floors, original woodwork. Secure keypad entry. Spacious cozy apartment with full kitchen and dining room. Owner on adjoining premises. Street parking. Minutes to Sports Factory, downtown nightlife, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory & Sinnissippi Gardens. 5 blocks to river and rec path. Quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. Not suitable for children under 6.

4.97 out of 5 average rating, 156 reviews

Apartment in Lake Geneva

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

4.87 out of 5 average rating, 103 reviews

Cabin in Brodhead

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Caledonia holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Caledonia

5 out of 5 average rating, 3 reviews

Charming Townhouse Stay

LeslieRating, 5 stars2 weeks ago

We really liked the home! It had everything we needed and it was a very comfortable space, it felt like home. The couch and bed was very comfortable and loved the soft duvet and clean sheets. The home is located in a very nice neighborhood and felt safe the entire time. Having our own 2 car garage was a bonus. Anmol was a very responsive host and he was so polite and helpful. We have no regrets staying here, and would love to come back next time we visit. ⭐️⭐️⭐️⭐️⭐️

5 out of 5 average rating, 8 reviews

Flat in Loves Park

The Modern Haven / 3Beds / Excellent location

JillRating, 5 stars2 weeks ago

I'm originally from Rockford and visit at least once per year. I am rarely inspired to leave reviews. Karolina's place was EXACTLY as pictured and described. This is a nice sized 2 br, 1 ba apartment in a 4-plex. You park directly in front of the unit, making it easy to bring in your suitcases. Karolina provides clear instructions on how to access the unit, which is bright, sunny, cheerful and SPOTLESS. The kitchen and bathroom are fully stocked with everything you could need (except food, lol), all of higher quality. The bed linens, and the manner in which the beds were made, were impressive. Definitely giving 5-star hotel vibes. Overall, of all the AirBnbs I've stayed in, this was the most comfortable. By that, I don't mean the beds, etc. I mean emotionally & psychologically comfortable, which is probably more important than anything else. Karolina clearly understands the meaning of hospitality. It is evident a lot of thought and planning went into her Modern Haven.

4.97 out of 5 average rating, 32 reviews

Cottage in Winnebago

Relax. Recharge. Reconnect.

SimiRating, 5 stars5 days ago

We were in the area for a wedding and to visit family. Nina was a great host. Decor is old with new. Our 17 year old loved the little kids nook even though she's 17.. lol Everything was perfect. We have stayed at many airbnb and this is one of our favorites. As an airbnb owner ourselves we know what needs to be in a rental and Nina did not disappoint us. I had to show it off to our family so they would tell other family members when they are in the area. We give Nina a A+++

5 out of 5 average rating, 10 reviews

Charming Pet-Friendly Rockford Escape

William JRating, 5 stars3 days ago

Michelle’s home was large, comfortable, and clean. Great yard for our dog to run around and do her business. Michelle also left special treats for our dog. Great experience, we would stay again if we were in Rockford

5 out of 5 average rating, 22 reviews

Safe perfect location near everything, 3+ bedrooms

Deborah JRating, 5 stars2 weeks ago

Stanton’s place was quiet and peaceful. We felt very safe there. There was plenty of space for the four of us. The house was very clean. We enjoyed the Keurig coffee both mornings. We would gladly stay there again if in the area.

Superhost

4.9 out of 5 average rating, 30 reviews

Rockford Rural

BrandonRating, 5 stars1 month ago

Danielle was very responsive, it was a nice get away for me and my friends . I would definitely book with her if I was you .

4.97 out of 5 average rating, 96 reviews

Home in South Beloit

Beautiful Craftsman Style Home w/ Fenced Yard

Wendy MarieRating, 5 stars1 day ago

OMG. We're traveling from the extreme West coast to the extreme East coast and are staying in Airbnb's. Its been kind of a learning experience. We are traveling with dogs who need a fenced yard and two pickup trucks towing grossly overweight (haha) U-Haul trailers. We've struggled through steep driveways, narrow driveways, busy streets -- this made backing out a major grade 10 challenge. There were comical deeply grooved one-lane cowpaths that threatened to bottom us out. Then, common necessities like a Kleenex or plastic wrap were absent -- just annoyingly inconvenient after spending 12 hours on the road. Ok, at the end of the day, they all had a comfy bed and that made it good. I checked with Anthony on the fenced yard and the parking situation first -- he was incredibly responsive and we booked last-minute the morning of. The home was fantastic. Nothing was missing and we wanted for nothing. There was street parking so we just simply pulled in and out. Nothing but praise !!