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Cottage vacation rentals in Caledonia

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Top-rated cottage rentals in Caledonia

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

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Top guest favorite
A cozy four-season porch features light wood paneling and large windows offering views of the outdoors. Comfortable seating, including woven chairs, is arranged around a small space, with decorative elements adorning the walls. A small electric fireplace provides warmth and ambiance.
Cottage in Trevor

The Lakehouse-3bdr/Lakefront/Wi-Fi

Enjoy your stay at this cozy cottage just steps away from beautiful Cross Lake and 5 minutes from Antioch, IL. This 3bdr, 1bath house features a 4 seasons porch so you can relax and unwind all year. Our large yard provides ample space to enjoy the stunning view. From May-Sept 30th, you will also have access to our shared pier. Enjoy swimming, boating, fishing or other nearby activities: skiing, golfing and ziplining. Beach chairs/toys, fire pit, grill, games and folding chairs are also provided.

4.98 out of 5 average rating, 164 reviews
Superhost
A cottage exterior is showcased with a well-maintained wooden deck and black railings. A welcoming front door is featured, which is flanked by two windows. The surroundings include a manicured lawn with small flower beds, enhancing the cottage's inviting appearance.
Cottage in Antioch

#4: Cute 2 bedroom cottage on the beach!

Relax & make lasting memories at this peaceful 2-bedroom cottage at Turtle Beach Marina. Enjoy the sandy beach on the lake, rent a boat or kayak, & unwind with summer drinks at the beach bar. A restaurant & game room (slots) are right on the property. (Bar & slots open mid-May through October.) Celebrating something special? Add a $75 package: 🌹Romantic Package: rose petals, candles, wine, & chocolates. 🎂 Birthday Package: HBD banner, balloons, 10-inch cake, & candles. Let us know in advance!

4.82 out of 5 average rating, 135 reviews
Guest favorite
A cozy living room features a soft, light-colored couch and a blue accent chair, set against a deep blue wall. Natural light enters through large windows, illuminating the hardwood floor and woven area rug. Decorative accents include wall art and a stylish coffee table.
Cottage in Racine

Historic cottage close to Lake Michigan

Get away for a relaxing weekend, enjoy a beautiful historic 1930's Tudor mini castle cottage! Blocks from the shoreline, beaches, running paths, and Racine Zoo. Visit one of the 50 top beaches in the US – North Point beach. Surrounded by bike paths and parks, Racine Marina, Racine Museum, Wind Point lighthouse, farmers markets and downtown Racine. 90 min. from Chicago area, Milwaukee 35 min. north, Kenosha 20 min. south. The property has been inspected and licensed, professionally cleaned.

4.91 out of 5 average rating, 101 reviews
Top guest favorite
The cottage features a charming exterior with a navy blue façade and a welcoming front door. American flags are displayed, and lush greenery includes a variety of colorful flowers and trees. Sunlight filters through the leaves, creating a serene and inviting atmosphere.
Cottage in Delafield

Lake Country Guest Cottage & Sauna

This 1930s fisherman’s cottage is tucked away and feels like you’re in the Northwoods or at your own private resort, yet is so close to it all. It is truly a recreation haven due to the proximity of lakes and rivers, as well as State and county parks. This is a quiet neighborhood and the cottage is amazing for relaxation- NOT bachelor/bachelorette parties; hotels are best for that. Choose from many amazing restaurants, within a mile or stay in to cook and end the night with a sauna session.

5.0 out of 5 average rating, 83 reviews
Guest favorite
A well-maintained cottage is set in a spacious yard surrounded by green grass and large trees. Outdoor seating is arranged near the water, with colorful chairs facing the waterway. The property features steps leading to a wooden deck, enhancing the connection to the scenic surroundings.
Cottage in Fox Lake

Lakefront Cottage with Gorgeous Sunsets

Great cottage so close to the water you can fish right off the deck, bring your boat right up to the dock and drive it all over the chain of lakes and out to dinner. Endless things to do on the chain, tons of restaurants, sand bars, fishing, bars, boats, etc. Then, watch the sunset at the beach right outside your door before retreating for the night into the cottage. The yard is fenced in, with a fire pit and is shared with permeant residence and another house I air bnb but is yours to enjoy

4.95 out of 5 average rating, 20 reviews
Top guest favorite
Cottage in Burlington

The Butterfly Cottage

Your summer get-away is perfect at The Butterfly Cottage on Honey Lake! Relax and enjoy the serenity of the lake and all the natural beauty of the season! This is a cozy cottage on Honey Lake, just 4 miles from downtown Burlington and 13 miles from Lake Geneva. Alpine Valley for concerts and skiing, fishing on Honey Lake or nearby Browns Lake as well as shopping in Lake Geneva are the highlights of the area! There are hiking/walking trails all around as well as rustic roads to explore.

4.98 out of 5 average rating, 102 reviews
Superhost
A vibrant purple room features a suspended chair swing and St. Andrew's Cross against a backdrop of textured curtains. LED lights add a soft glow, while a television mounted on the wall complements the unique decor, creating an intriguing space for intimate exploration.
Cottage in Riverwest

MKE Pleasure Paradyz - BDSM - Adult Themed Cottage

Ignite your senses at The MKE Pleasure Paradyz. Indulge in the erotic arts of St. Andrew's Cross, Tantra couch, and Adult Swing. Have an experience of pleasurable memories. This meticulously designed cottage offers an immersive and sensual experience with elements of Kink, BDSM and Role Play. Every detail, from the pristine cleanliness to the carefully curated ambiance. Seek to explore new dimensions of intimacy or simply unwind, we provide a welcome environment to enhance your desires!

4.96 out of 5 average rating, 23 reviews
Top guest favorite
A charming white cottage sits within a landscaped area, surrounded by a white picket fence. Lush greenery and flowering plants are visible in the foreground, while trees stand in the background under a clear blue sky.
Cottage in Hartland

Cozy cottage in the heart of Lake Country

Entire cottage in Lake Country nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, carriage house and barn. A country setting with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.). NOTE: exempt from accepting service and emotional support animals.

4.95 out of 5 average rating, 167 reviews
Guest favorite
Cottage in Lake Geneva

Cozy Cottage-Core Escape | Walk to Beach & Cafés!

Kinfolk Cottage is our treasured retreat located in Lake Geneva’s historic Maple Park district. When we’re not gathering here with friends and family, we open our doors to guests. This chic, restored gem blends timeless character with modern comfort. An easy walk to local cafes, boutiques, and the beach, or simply stay in and soak up the cottage charm. Designed for making memories that last a lifetime, Kinfolk Cottage captures the true spirit of classic Lake Geneva living. Welcome!

4.93 out of 5 average rating, 174 reviews
Top guest favorite
The exterior of the cottage is showcased, with dark wood siding and a well-maintained garage door. Lush green trees surround the property, providing shade and a natural feel. A walkway leads to the entrance, enhancing the inviting atmosphere of the home.
Cottage in Mukwonago

Charming Phantom Lake Cottage

Come relax at our cottage located on Phantom Lake. This 2 bedroom, 2 bath, plus sleeping loft area home is comfortably furnished and a perfect space to enjoy all lake life offers year round. Free public boat launch located nearby with our private pier/dock and anchored swim raft available for use on a seasonal basis along with multiple kayaks, paddleboard, and paddle boat on site. Attached composite deck and crushed stone fire pit area are perfect spots to enjoy the outdoors.

4.97 out of 5 average rating, 67 reviews
Top guest favorite
Cottage in Wonder Lake

The Cozy Lake House, Dm me ?s Lake Front Property!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

4.94 out of 5 average rating, 177 reviews
Top guest favorite
A cozy sunroom features a round dining table surrounded by four white chairs, with yellow placemats set for meals. Natural light floods in through multiple windows, illuminating the space. A door leads outside, enhancing the connection with nature.
Cottage in Burlington

Cottage Escape near Private Browns Lake Beach

Families, Creatives, and Professionals: welcome to our comfy cottage! You'll enjoy exclusive access to private Cedar Park beach on Browns Lake, a wooded yard with great privacy, a cozy sunroom, and two desks ideal for a personal creative retreat or remote work. Charming downtown Burlington has shopping and restaurants, and Lake Geneva and Alpine Valley are both 20 minutes away. Activities year-round: swimming, boating, fishing, hiking, snowmobiling, ice fishing, and skiing.

4.92 out of 5 average rating, 86 reviews

Popular amenities for Caledonia cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Superhost
Cottage in Pewaukee

Lakeside Pewaukee Cottage • Hot Tub • Paddleboards

4.91 out of 5 average rating, 34 reviews
Guest favorite
The interior of the cottage features a cozy seating area with a blue couch adorned with yellow cushions. A coffee table made of wicker sits atop a soft yellow rug. A kitchenette is visible, along with a dining area illuminated by natural light from large windows.
Cottage in Antioch

#5 Tiny Lake Cottage at Cypress Resort & Marine

4.86 out of 5 average rating, 235 reviews
Superhost
A spacious bedroom is reflected in a circular green-framed mirror. The light wood walls complement the bed dressed in a checkered quilt. A bedside lamp softly illuminates the room, while a white dresser and a window invite natural light.
Cottage in Antioch

#2 Historic Lake Cottage -Cypress Resort & Marine

4.91 out of 5 average rating, 131 reviews
Superhost
The illuminated hot tub is situated on the back deck, showcasing a calming blue glow against the night backdrop. Surrounding areas are softly lit, creating a serene atmosphere for relaxation. The tub is equipped to accommodate 3-4 individuals, inviting guests to unwind outdoors.
Cottage in Fox Lake

2/1 Cozy Cottage with Hot Tub Gazebo and Lake View

4.76 out of 5 average rating, 93 reviews
Guest favorite
A cozy living area features warm wood paneling and two lamps providing soft lighting. A beige couch is adorned with decorative pillows, while a wooden coffee table is centered. A small dining table with chairs is visible, along with a glimpse of the kitchen area.
Cottage in Antioch

#8 Hillside Cottage at Cypress Resort & Marine

4.89 out of 5 average rating, 89 reviews
Superhost
A living area features a blue sofa and a light-coloured coffee table, enhancing the warmth of the space. Two lamps stand on each side of the sofa. In the background, a dining area is visible with a round table and four chairs under natural light.
Cottage in Antioch

#3 Charming Lake Cottage - Cypress Resort & Marine

4.78 out of 5 average rating, 9 reviewsA charming cottage is presented with a well-maintained exterior surrounded by a white picket fence. The structure features large windows and a distinctive rooftop deck. Lush greenery is visible, enhancing the inviting atmosphere of the outdoor space.
Cottage in Antioch

The Blue Roof Cottage @ Cottages on Petite Lake

4.52 out of 5 average rating, 29 reviewsA fully-fenced backyard features a fire pit surrounded by seating, offering a view of the tranquil lake. The deck area includes lounge chairs and a glimpse of a moored boat, highlighting the natural beauty of the outdoor space.
Cottage in Antioch

The Cozy Cottage @ The Cottages on Petite Lake

4.74 out of 5 average rating, 132 reviews

Pet-friendly cottage rentals

Guest favorite
A charming orange bungalow is framed by lush greenery. The exterior features large windows and a welcoming front door with a star motif. The overall structure reflects a cozy, cabin-like feel, inviting guests to relax and enjoy the surrounding nature.
Cottage in Twin Lakes

Twin Lakes Bungalow

4.91 out of 5 average rating, 75 reviews
Superhost
A light-filled living room features a comfortable sofa adorned with a throw blanket. A glass coffee table is positioned on a textured rug, with a lamp adding soft illumination. Plants are present, along with framed artwork and a cozy side table, creating a welcoming ambiance.
Cottage in Bay View

The Snug Irish Cottage (King Bed)

4.93 out of 5 average rating, 29 reviews
Guest favorite
Cottage in Antioch

Key House at Petite Lake Resort, #4

5.0 out of 5 average rating, 12 reviews
Guest favorite
An open-plan living area showcases a modern kitchen with stainless steel appliances and a central island. A dining table for six is situated near a large flat-screen TV. Natural light floods the space through multiple windows, enhancing the sleek design and neutral tones.
Cottage in Riverwest

Private Cottage w/ City Views

4.96 out of 5 average rating, 54 reviews
Guest favorite
Cottage in Lake Geneva

Cozy Lake Geneva Cottage | Walk to Town | Pets Ok

4.96 out of 5 average rating, 116 reviews
Guest favorite
A spacious kitchen and living area feature modern appliances and wooden cabinetry. Four black bar stools are positioned around a kitchen island, and natural light is invited through large windows. A cozy sectional sofa and a decorative area rug add warmth to the space, complemented by charming wood paneling.
Cottage in Nashotah

Okauchee Lake - Newly Remodeled Cozy Cottage

4.97 out of 5 average rating, 29 reviews
Cottage in Fox Lake

Waterfront Fox Lake Vacation Rental w/ Fire Pit!

4.88 out of 5 average rating, 8 reviews
Guest favorite
A cozy living area features a brown leather sectional sofa adorned with colorful cushions. A light rug covers the floor, while warm lighting highlights the wooden ceiling and walls. Doorways lead to other rooms, adding to the inviting ambiance.
Cottage in Hartford

Cheerful cottage in the middle of the Kettles.

4.92 out of 5 average rating, 66 reviews

Private cottage rentals

Guest favorite
A charming lakefront cottage features a vibrant blue metal roof and a spacious deck. Surrounded by greenery, the outdoor area includes lounge seating, while the wooden pier extends over the water. Two large windows reflect natural light, enhancing the welcoming ambiance.
Cottage in Twin Lakes

Lakefront Cottage Spectacular Sunsets Boat Rental

4.97 out of 5 average rating, 31 reviews
Top guest favorite
A cozy corner features two blue armchairs positioned around a wooden game table, creating an inviting space for leisure activities. A remote-controlled electric fireplace is centered below a decorative artwork, with windows providing natural light and views of the outside.
Cottage in Lake Geneva

Walkable to Lake & Downtown Lake Geneva

5.0 out of 5 average rating, 62 reviews
Superhost
Four white Adirondack chairs are positioned in a row facing a serene lake, framed by trees and a colorful sunset. A small white table stands between two of the chairs. The scene conveys a peaceful outdoor space ideal for relaxation.
Cottage in Burlington

Beautiful Cottage w/ Lake Views and Private Beach

4.58 out of 5 average rating, 19 reviews
Guest favorite
The exterior of a cottage is shown, featuring two sets of wooden stairs leading up to a multi-level deck. Lush green grass surrounds the structure, which is partially shaded by a nearby tree. A vibrant umbrella adds color to the outdoor space.
Cottage in Fox Lake

All Season Sunset Cottage on Pistakee Lake

4.81 out of 5 average rating, 202 reviews
Top guest favorite
A bright bedroom features a spacious bed with a white duvet and decorative pillows, framed by two woven pendant lights. Natural light pours in through a large window, illuminating the soft beige walls and a patterned area rug beneath the bed.
Cottage in Lake Geneva

Close to Town + Beach • Historic Pemberley Cottage

4.96 out of 5 average rating, 114 reviews
Guest favorite
The exterior of the cottage features a modest entrance with a stone walkway leading to the door. Flower boxes with seasonal plants are positioned under the windows, adding color to the façade. The surrounding area has a mix of stone and shrubbery, contributing to its rustic charm.
Cottage in Lake Villa

Laura’s Little Cottage

4.8 out of 5 average rating, 166 reviews
Guest favorite
A wooden deck is visible, featuring a glass-top dining table surrounded by metal chairs. The tranquil lake stretches out beyond, with clear blue skies and calm waters. A tree's branches provide shade, enhancing the outdoor seating area by the water.
Cottage in McHenry

Lakefront Views, Free Water Sports!!

4.88 out of 5 average rating, 58 reviewsA tranquil lake view at sunset, reflecting soft pink and orange hues in the water. The opposite shoreline is lined with charming houses framed by a backdrop of diverse trees, contributing to a peaceful ambiance.
Cottage in Burlington

Great getaway in Lily Lake Near Country Thunder

4.5 out of 5 average rating, 18 reviews

Destinations to explore