Family-friendly vacation rentals in Machesney Park

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Top-rated family-friendly rentals in Machesney Park

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in Shirland

4.89 out of 5 average rating, 219 reviews

Historic limestone farmhouse, nature preserve.

Historic 1840's limestone home ,once owned by Sidney Smith, first nationally syndicated cartoonist of The Gumps. Located on 19 acres adjacent to 500 acre wetland conservation area with miles of hiking/skiing trails along the pristine sandy Sugar River for canoeing, birdwatching, or fishing. Ideal for star-gazing, with minimal lighting from neighbors. Enjoy the outdoors from stone patio, including tables, BBQ, and seating for 15, with fireplaces indoors and outside. Sand pile and toys nearby

May 14 – 21

€ 245 per night

Guest favorite

Loft in Woodstock

4.96 out of 5 average rating, 170 reviews

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

Jul 24 – 31

€ 140 per night

Guest favorite

Farm stay in Caledonia

4.89 out of 5 average rating, 104 reviews

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.

Feb 8 – 15

€ 150 per night

Guest favorite

Cabin in Oregon

4.95 out of 5 average rating, 147 reviews

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. Pets allowed by adding them to total guest count. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

Apr 6 – 13

€ 243 per night

Guest favorite

Farm stay in Hampshire

4.96 out of 5 average rating, 211 reviews

Country Farmhouse with Multiple Rooms

This 1890s farmhouse gets lots of natural light and offers all the comforts of home. From the comfy quilts to beautiful grounds, make this your home away from home for your stay with us. Just 35 minutes from O'Hare International Airport and a short drive off I-90, our home is a convenient location between Chicago and Rockford, Illinois. Host on-site in attached live-in quarters. Breakfast is available upon request for $10 per person. Please note information below on WiFi access.

Jul 11 – 18

€ 187 per night

Guest favorite

Apartment in Rockford

4.94 out of 5 average rating, 454 reviews

Upscale Urban Retreat 1 bedroom, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

Sep 20 – 27

€ 106 per night

Guest favorite

Bungalow in Rockford

4.95 out of 5 average rating, 381 reviews

Arts and Crafts Bungalow with Outdoor Space

We welcome you to a centrally located two-bedroom Arts & Crafts Bungalow. Ideally situated near sports venues, shopping, museums, and restaurants, the house is a perfect place for families, professionals, and couples. We have free on street parking in front of the home, We are 10 minutes away from the UW Sports Factory, Anderson Japanese Gardens, and Nicholas Conservatory. We are 20 minutes away from Anna Page Park and Rock Cut State Park.

Jun 21 – 28

€ 118 per night

Guest favorite

Guest suite in Rockford

4.9 out of 5 average rating, 185 reviews

Historic Downtown Riverfront Suite

Unique downtown location on the banks the Rock River. The River Suite is in the lower exposed level of a historic craftsman bungalow. Adjacent to Beattie Park you are steps from the Historic Coranado Theater and Riverfront Museums Park. Directly across the river is the popular Prairie Street Brewhouse/docks. The summer is very active with boating and live music that you can enjoy from the patio or private lower shore deck.

Mar 25 – Apr 1

€ 120 per night

Superhost

Tiny home in Williams Bay

4.87 out of 5 average rating, 181 reviews

The Tiny Bay House

Romantic hideaway tucked in the woods close to Geneva Lake, where you'll experience all the best of all worlds. This intimate tiny house includes a full kitchen, luxury bathroom, bbq grill, fire pit and a giant private yard. Play at the lake all day, and relax at your tiny home among the woods. This house has its own yard but is right next to THE BAY CHALET. Book both together for a family getaway!

Nov 27 – Dec 4

€ 222 per night

Guest favorite

Apartment in Albany

4.93 out of 5 average rating, 159 reviews

Sugar River Hideaway

Newly renovated, 3-bedroom vacation home located on the Sugar River in downtown Albany. Albany is a quaint little town with a lot to offer. Enjoy tubing/canoeing down the river, a diner, pizza place, Italian restaurant, 3 taverns, and a bowling alley all within the downtown block. With being only 30 miles away from Madison and 17 miles from New Glarus, Albany is a prime location for your stay!

Apr 10 – 17

€ 115 per night

Guest favorite

Home in DeKalb

4.95 out of 5 average rating, 237 reviews

Cozy home in front of the park and close to NIU

This cozy house is set in a quiet and safe neighborhood in DeKalb IL, it has plenty of sunlight, comfortable furniture, high speed internet and TV., your pet will love our big back yard!, there is a park across the street and trails at walking distance. We are five minutes away from NIU and downtown DeKalb, and also very close to supermarkets, restaurants and coffee.

Apr 7 – 14

€ 114 per night

Guest favorite

Loft in Rockford

4.93 out of 5 average rating, 409 reviews

Jackson’s Urban Retreat + Patio

Cool, modern downtown city loft located walking distance from 20+ restaurants, shops and entertainment venues. Private outdoor patio and private parking spots. If you are looking to enjoy sports, dining, arts and theater without getting in a car, this is the space for you. Located above Abreo Restaurant, all guests receive 10% discount during stay

Nov 23 – 30

€ 137 per night