
Holiday rentals in Brooklyn
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Top-rated holiday rentals in Brooklyn
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Charming Campus Area Home • Entire Home Near UW
Steps to Camp Randall & an easy walk to UW–Madison! Spacious home for up to 10 guests with a comfortable layout, multiple bedrooms, full kitchen, and inviting gathering spaces. Enjoy the back patio—perfect for unwinding after a day on campus or exploring the city. Ideal for Badgers game weekends, family visits, and group stays. Please note: during football weekends, the host may use the garage and part of the driveway for tailgating; parking may be shared. Cleaning fee $150. No pets or smoking.
4.98 out of 5 average rating, 285 reviews
Luxury Lakeside Oasis- 4 Bed / 3 Bath Lake Home
Enjoy time with your loved ones at our luxury lake front oasis. Breathtaking views combined with the ideal Middleton location & extensive updating make our home the perfect vacation destination. Huge windows maximize gorgeous views of 60+ feet of lake frontage. A fully updated kitchen boasts custom everything. Our home features: 4 bedrooms, 3 bathrooms, lofted office, open kitchen with an island & dining table. A short drive (5-7 mi) to UW Campus, Camp Randall, Kohl Center & Wi State Capitol
5.0 out of 5 average rating, 20 reviews
4 Season Fun: Private Fish Pier, Cozy Decks, Grill
4Br/2.5bath, beds for 12 adults+, on water with Private Pier, fire pit, gas grill, covered decks, 2 acre yard + woods. 4 SEASONS OF FUN: Fall Fest Farms, Wineries, Ice Fishing, Snowmobiling & Skiing. Lake Koshkonong is one of WI’s largest, famous for boat-up restaurants/bars, Live Music & fishing. Located on 39/90hwy - 90 mins to Chicago, 30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living areas, playroom & more! Pets ok!
4.92 out of 5 average rating, 155 reviews
Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna
Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.
4.96 out of 5 average rating, 665 reviews
Comfortable Madison Area Retreat In The Trees
Tri-level duplex centrally located in Fitchburg. Nestled in a quiet residential neighborhood backing up to a small patch of woods for privacy. Feel away from it all with the sights and sounds of nature yet close to all the modern conveniences. Enjoy separated living spaces, a fully equipped kitchen (per WI health code, edible cooking supplies are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!
4.91 out of 5 average rating, 158 reviews
Le Gallus Palace - A Tiny House
Escape to Le Gallus Palais, a cozy tiny house on a peaceful farm just 20 minutes from Madison, WI. Surrounded by farm fields, and a chicken yard, with access to a spiral orchard with tame ducks and a koi pond, this private retreat offers charm, comfort, and serenity. Enjoy a restful stay with a comfy bed, kitchenette, and nature all around. Perfect for a romantic getaway, solo retreat, or creative escape. Get the best of both worlds - country vibe with modern amenities.
4.98 out of 5 average rating, 51 reviews
Luxurious & Spacious 4 BR Home w/o Cleaning Fees
Escape to our stunning Madison home! Luxuriate in the sleek contemporary design, spacious living areas with high-end finishes and tasteful furnishings. Unwind in the comfortable bedrooms with ample storage. Step outside to our backyard oasis for al fresco dining and relaxation. Our exceptional customer service and thoughtful touches guarantee an unforgettable stay. Close to Madison's best shopping, dining, and entertainment. Book now for an experience you won't forget!
4.95 out of 5 average rating, 110 reviews
The Dairy at the Wegmueller Farm
Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.
4.99 out of 5 average rating, 175 reviews
Main St 1 Bdrm - Steps to the Wine Reserve!
Welcome to historic downtown Oregon! Step into the past while enjoying modern comfort in this beautiful space, which once housed our 1st library! Just steps away from locally owned coffee and gift shops, a wine reserve, and amazing restaurants! With convenient access to Madison (14 mi), experience the best of both worlds – small-town tranquility and urban excitement. Whether for work or leisure, welcome home!
4.97 out of 5 average rating, 132 reviews
Contemporary home near Madison
Located in a quiet neighborhood only twenty minutes away from Madison, this contemporary home is the perfect place for large groups. The home has three spacious bedrooms with a large kitchen and two outdoor patios for entertaining. It is a great place to relax and enjoy the Wisconsin weather inside and out! If you require additional sleeping accommodations, an air mattress can be made available.
4.99 out of 5 average rating, 234 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!
4.93 out of 5 average rating, 225 reviews
Stone Farmhouse Stay
Stay at this unique and tranquil retreat nestled on our farm between Paoli and New Glarus. Our family spent 2 years restoring this 1840’s stone house (that was the original house to our farm) has all the charm of the past with all the luxuries of today. The house is also staged with beautiful furnishings and decor from our shop in Paoli. Let us know if you see anything you would like to buy.
4.95 out of 5 average rating, 39 reviewsPopular amenities for Brooklyn holiday rentals
Other great holiday rentals in Brooklyn

The Allen Creek Apt. Historic Downtown Evansville
4.97 out of 5 average rating, 38 reviews
Waterfront - Hot Tub - Sauna - Game Room - Pets
4.85 out of 5 average rating, 71 reviews
Hot tub with a wooded view
4.96 out of 5 average rating, 81 reviews
Bees on Main: sweeter than ever
5.0 out of 5 average rating, 41 reviews
Firefly Wood Lodge
4.93 out of 5 average rating, 27 reviews
Beautiful Lake Home- On Lake Waubesa
4.9 out of 5 average rating, 49 reviews
Spacious & Modern Home w/ Deck in Oregon!
4.61 out of 5 average rating, 33 reviews
Driftwood Den Apt-Downtown Stoughton- Sleeps 7
4.92 out of 5 average rating, 13 reviewsDestinations to explore
- Chicago Holiday rentals
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- Devil's Lake State Park
- Alpine Valley Resort
- House on the Rock
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Wollersheim Winery & Distillery
- University of Wisconsin
- Cascade Mountain
- Governor Dodge State Park
- Henry Vilas Zoo
- Camp Randall Stadium
- American Players Theatre
- Chazen Museum of Art
- Tyrol Basin
- Overture Center For The Arts
- Monona Terrace Community And Convention Center
- Dane County Farmers' Market
- Madison Childrens Museum
- Alpine Valley Music Theatre
- Cave Of The Mounds Lowest Point
- Rock Cut State Park
- Discovery Center Museum
- Blue Mound State Park
- Parfrey's Glen State Natural Area





