Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favourite

Home in Juneau

4.85 out of 5 average rating, 133 reviews

Take a Break at Lakeside Acres

Lakeside Acres; a 2-bedroom, 1 bath vacation rental home located on beautiful Lake Sinissippi. Open concept living area with furnished patio and private dock. This newly updated home provides the perfect summer getaway or winter retreat for family and friends. Whether you spend your days kayaking with the complimentary kayaks, exploring Horicon Marsh, or soaking up the sun on the dock, you're sure to have an unforgettable stay in this lakefront hideaway. Note: Docks are not in the lake Nov-Apr.

Superhost

Condo in Wisconsin Dells

4.83 out of 5 average rating, 231 reviews

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

**INDOOR & OUTDOOR POOL ACCESS | DISCOUNTED ATTRACTION TIX | WATERFRONT** The Riverwalk Retreat is the perfect spot to enjoy your next WI Dells trip with friends or family. This cozy vacation rental is located at the Sunset Cove Condo complex just 2 blocks off of Broadway & overlooks Crandalls Bay. Enjoy your morning coffee with a spectacular view of the WI River & the adjoining bay. This central location provides easy access to the area’s many athletics venues, nightlife, dining, & shopping.

Guest favourite

Home in New Lisbon

5 out of 5 average rating, 35 reviews

Retreat on the Beach! EV Friendly! Hot tub!

Escape the craziness of life in this new construction home. This Beach Cottage home is perfect for your family to enjoy all Wisconsin seasons. Beach Lake is a clear Six acre private lake with a sandy bottom located near Buckhorn State Park, Castle Rock Lake, lots restaurants, and is only a 30-minute drive to the Wisconsin Dells. Our home has 4-bedrooms and 2 full baths, Full Kitchen, huge basement, patio, deck, private beach, insulated/heated garage with a EV charger. Hot tub October 2023.

Top guest favourite

Bungalow in Richland Center

5 out of 5 average rating, 291 reviews

Glory View Ridgetop Bungalow

Farmhouse Bungalow sits on top of a ridge in the Southwest WI driftless area, boasting spectacular views. A site that works for anyone from a relaxing retreat to a great spot for adventures. Fall photography dream, cyclists paradise, star gazing/campfire, hiking, kayaking, canoeing, fly fishing, Frank Lloyd Wright, WI Dells and other local attractions. The home was completely renovated with all the modern conveniences but the Farmhouse charm. A sleeping loft adds additional functionality.

Guest favourite

Bungalow in Lake Geneva

4.97 out of 5 average rating, 141 reviews

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

Top guest favourite

Home in Lake Geneva

4.98 out of 5 average rating, 144 reviews

Updated luxury country getaway short walk to lake!

Luxury getaway close to private beaches, downtown Lake Geneva, and many area amenities. Relax in comfort in this newly renovated 3-bedroom. Enjoy all that the Lake Geneva area has to offer while unwinding in a modern, comfortable retreat. Conveniently located a 3-min walk to Lake Como and a 10-min drive to downtown Lake Geneva. Charming golf cart community with so much to do. Perfect for couples, families, and business travelers. Ideal space for up to 4 adults and great for families of 5.

Guest favourite

Home in Lake Geneva

4.94 out of 5 average rating, 34 reviews

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

Top guest favourite

Condo in Wisconsin Dells

4.97 out of 5 average rating, 472 reviews

COZY, Lakefront, Fireplace, Free Kayaks

Relax on the porch and watch the boats glide by, soaking in the serene lake views. Whether you're looking for relaxation or recreation, our condo offers the best of both worlds. Book your stay today and experience the ultimate lakeside escape! Resort-Style Amenities • Indoor and outdoor pools • Hot tub • Walking distance to Noah's Ark • Proximity to numerous restaurants and activities • First Responder Discounts • Smart TVs • Jetted Tub • Fireplace • Washer/Dryer

Superhost

Condo in Wisconsin Dells

4.84 out of 5 average rating, 281 reviews

Williamson Family Condo at Lighthouse Cove

NO SMOKING Upgrade to our Noah's Ark package after booking! Williamson Family Condo II is recently updated and located in Lighthouse Cove on Lake Delton in the heart of the Dells. Enjoy beach access, in & outdoor pools w/ hot tubs, and convenient parking. This condo is great for a couples or families. Let the older kids wander to and from Noah's Ark or go fishing at the lake while you take a much-deserved time out. Inquire about using our boat slip.

Top guest favourite

Home in McFarland

4.88 out of 5 average rating, 146 reviews

Lovely Waterfront Two Bedroom House

Lovely two bedroom, one bath in a rural residential area of McFarland on inlet that connects to Yahara River and Lake Kegonsa (house is not directly on lake or river). The home is situated next to a charming campground and marina in nature. Walkable fishing areas. Lake Kegonsa State Park Trail is nearby for walking or snowshoeing. Just a 20 minute drive to downtown Madison! NO PARTIES. You will be asked to leave if there is any party activity seen.

Guest favourite

Cabin in Wisconsin Dells

4.88 out of 5 average rating, 215 reviews

Lake-view 3-bedroom Cabin Home on Lake Delton

Our place is close to ALL Lake Delton, WI Dells Downtown attractions. You’ll love our place because of the views of lake & pine trees, quiet setting, brand-new remolded interior with upscale furnishings, high ceilings, and the cabin coziness. Our Large, cabin accommodates up to 8 people very comfortable at over 1600 sq. ft. Best Resort in Town!!! Family fun atmosphere with two sandy beaches & large swimming pool. Kids love to fish off the piers.

Guest favourite

Home in Lake Geneva

4.97 out of 5 average rating, 153 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!