See all properties

Overlook Legacy - Historic 1907 Home on the Milton Square

Exterior

Private kitchen

Private kitchen

Dining

Terrace/patio

Don't miss out! Price and availability may change

House in Wisconsin

8 guests · 3 bedrooms · 2 baths

Reasons to book

High-end valueWell priced for this area

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Includes essentials and more

About this house rental

Discover Overlook Legacy: a charming 1907 historic three-bedroom home in Milton, WI, part of our beloved Overlook collection near Lake Koshkonong. Sleeps 7-8 with timeless elegance—original hardwood floors, high ceilings, fireplace, full kitchen, and modern amenities like Wi-Fi & laundry. Steps from the local town square; just minutes to the lake. Perfect for families, getaways, or mid-term stays. Experience historic charm with exceptional hospitality!

Amenities at Overlook Legacy - Historic 1907 Home on the Milton Square

Non-smoking

No pets allowed

Family friendly

Map of Wisconsin

city location on map

Nearby attractions

EAA Aviation Museum

Horicon National Wildlife Refuge

$$$$

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Overlook Legacy - Historic 1907 Home on the Milton Square. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Overlook Legacy - Historic 1907 Home on the Milton Square pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Overlook Legacy - Historic 1907 Home on the Milton Square?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.

Explore similar stays in Wisconsin

Explore all stays

Updated 3 bedroom in the UW Arboretum

16 guests · 3 bedrooms · 1 bath

WiFi/Internet · Air conditioning · Washing machine

Experience the best of Wisconsin with this House available for $316. This property is equipped with amenities including Air conditioning, Dryer and WiFi/Internet, and more.

13 Mi to University of Wisconsin: Suburban Home

10 guests · 5 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · TV

This House for $320 in Wisconsin, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

Par-fect Escape on Lake Windsor Golf Course

10 guests · 1 bedroom · 3 baths

Free WiFi/internet · Air conditioning · Bar

House in Wisconsin, for $270 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(7 Ratings)

20min to Capitol - Garage - Yard - KING Bed - Pets

16 guests · 4 bedrooms · 2 baths

WiFi/Internet · Air conditioning · TV

Indulge in a peaceful retreat at 20min to Capitol - Garage - Yard - KING Bed - Pets, our elegant House in Wisconsin. Enjoy amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

You can save with One Key

Par-fect Escape on Lake Windsor Golf Course

8 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Washing machine

The best choice in Wisconsin for House, for $295 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

9.6 / 10.0

Outstanding(11 Ratings)

Entire duplex next to waterfront

16 guests · 4 bedrooms · 2 baths

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Wisconsin, at $321 per night for your next great vacation.

9.6 / 10.0

Outstanding(16 Ratings)

Entire 3 Bedroom with Fireplace - sleeps 12

10 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · TV

Enjoy the best of Wisconsin in our House, Entire 3 Bedroom with Fireplace - sleeps 12. A stunning property with amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

You can save with One Key

9.0 / 10.0

Outstanding(22 Ratings)

Stylish & Updated Bungalow

9 guests · 3 bedrooms · 1 bath

WiFi/Internet · Air conditioning · TV

This House in Wisconsin, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

10.0 / 10.0

Outstanding(20 Ratings)

Cheerful 3-bedroom cottage 2 blocks from the lake

8 guests · 3 bedrooms · 1 bath

Free WiFi/internet · Air conditioning · TV

Looking for the perfect place to call home during your trip to Wisconsin? This Cottage offers a comfort and style with top-notch amenities, including Air conditioning, Dryer and WiFi/Internet, and more.

10.0 / 10.0

Outstanding(14 Ratings)

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

12 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · TV

Looking for a Apartment in Wisconsin, this Apartment for $338 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

10.0 / 10.0

Outstanding(7 Ratings)

20min to Capitol - Garage - Yard - KING Bed - Pets

16 guests · 4 bedrooms · 2 baths

WiFi/Internet · Air conditioning · TV

This House for $279 in Wisconsin, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(25 Ratings)

Family Home w/ Deck, Yard, Dock on Rock River

15 guests · 5 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · Pool

This House in Wisconsin, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

7.0 / 10.0

Good(2 Ratings)

Boat Dock and Backyard Rock River Retreat

13 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Pool

Looking for a House in Wisconsin, this House for $331 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

You can save with One Key

10.0 / 10.0

Outstanding(14 Ratings)

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

12 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · TV

This Apartment in Wisconsin, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

10.0 / 10.0

Outstanding(11 Ratings)

Charming 3-bedroom Duplex unit in Cottage Grove

in Cottage Grove

8 guests · 3 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · TV

Indulge in a peaceful retreat at Charming 3-bedroom Duplex unit in Cottage Grove, our elegant House in Wisconsin. Enjoy amenities including Air conditioning, Dryer and Fireplace, and more.

10.0 / 10.0

Outstanding(76 Ratings)

Cozy cottage retreat that’s perfect for recharging.

8 guests · 3 bedrooms · 1 bath

WiFi/Internet · Air conditioning · TV

When traveling to Wisconsin, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $241 per night.

You can save with One Key

10.0 / 10.0

Outstanding(4 Ratings)

Remodeled home with pontoon rental 2 decks Private beach playground volleyball

10 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Air conditioning · TV

This House in Wisconsin, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

9.4 / 10.0

Outstanding(15 Ratings)

Cozy Lakefront House

10 guests · 4 bedrooms · 2 baths

Looking for a memorable stay in Wisconsin? Our House might just be what you're looking for. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more during your stay.

10.0 / 10.0

Outstanding(4 Ratings)

Remodeled home with pontoon rental 2 decks Private beach playground volleyball

10 guests · 2 bedrooms · 1 bath

Free WiFi/internet · Air conditioning · TV

Business stays, family stays, couples stay, getaway vacation, and rental in Wisconsin at Remodeled home with pontoon rental 2 decks Private beach playground volleyball for $245 for your next trip.

9.0 / 10.0

Outstanding(5 Ratings)

New Luxury & Spacious House in the Heart of Janesville

8 guests · 4 bedrooms · 1 bath

WiFi/Internet · Air conditioning · TV

Looking to create some memories in Wisconsin? Look no further than our House, New Luxury & Spacious House in the Heart of Janesville. Enjoy top-rated amenities including Air conditioning, WiFi/Internet and Kitchen, and more.

9.5 / 10.0

Outstanding(57 Ratings)

Rustic Lake home Retreat

9 guests · 3 bedrooms · 2 baths

Enjoy the best of Wisconsin in our House, Rustic Lake home Retreat. A stunning property with amenities including No pets allowed, Family friendly and Non-smoking, and more.

10.0 / 10.0

Outstanding(12 Ratings)

Spacious Lakehouse w/ Deck, Kayaks, & Dock!

12 guests · 4 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · TV

Looking for the perfect place to call home during your trip to Wisconsin? This House offers a comfort and style with top-notch amenities, including Dryer, Fan and Lake view, and more.

7.0 / 10.0

Good(3 Ratings)

New Luxury House in the Heart of Janesville

10 guests · 4 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Balcony/Terrace

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Wisconsin, at $251 per night for your next great vacation.

10.0 / 10.0

Outstanding(25 Ratings)

Spectacular Lakefront Home w/ Sandy Beaches, Pier and Firepit

8 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · TV

Looking for a House in Wisconsin, this House for $338 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

9.2 / 10.0

Outstanding(5 Ratings)

New Luxury & Spacious House in the Heart of Janesville

8 guests · 4 bedrooms · 1 bath

WiFi/Internet · Air conditioning · TV

Experience the best of Wisconsin with this House available for $255. This property is equipped with amenities including Air conditioning, WiFi/Internet and Kitchen, and more.

You can save with One Key

7.4 / 10.0

Good(3 Ratings)

Entertainment Haven! Firepit, Game Room, and Large fenced-in yard

8 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Washing machine

Business stays, family stays, couples stay, getaway vacation, and rental in Wisconsin at Entertainment Haven! Firepit, Game Room, and Large fenced-in yard for $286 for your next trip.

9.2 / 10.0

Outstanding(5 Ratings)

LAKE LIFE! AMAZING HOME FOR A GETAWAY! BOOK 3 NIGHTS GET 4TH FREE!

8 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · TV

Experience vacation in Wisconsin with our House, LAKE LIFE! AMAZING HOME FOR A GETAWAY! BOOK 3 NIGHTS GET 4TH FREE! . Enjoy amenities such as Air conditioning, Dryer and Fireplace, and more.

7.4 / 10.0

Good(3 Ratings)

Entertainment Haven! Firepit, Game Room, and Large fenced-in yard

8 guests · 3 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Washing machine

Nestled in Wisconsin, this House is perfect for your next vacation. Enjoy Entertainment Haven! Firepit, Game Room, and Large fenced-in yard's top-rated amenities, including Air conditioning, WiFi/Internet and Laundry services, and more.

You can save with One Key

9.0 / 10.0

Outstanding(78 Ratings)

Join us on the sandy shores of lake Koshkonong for an escape from the city

12 guests · 4 bedrooms · 3 baths

WiFi/Internet · Air conditioning · TV

Soak up the beauty of Wisconsin in our Cabin, Join us on the sandy shores of lake Koshkonong for an escape from the city. With a range of amenities such as Air conditioning, Dryer and Fireplace, you'll feel right at home.

9.9 / 10.0

Outstanding(33 Ratings)

Cozy Cabin at Lake Koshkonong

8 guests · 2 bedrooms · 1 bath

Looking to create some memories in Wisconsin? Look no further than our Cabin, Cozy Cabin at Lake Koshkonong. Enjoy top-rated amenities including Pets allowed and Family friendly, and more.