Search Vacation Homes in Oconomowoc

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 146 Vacation Homes in Oconomowoc with updated reviews, rates, and availability.

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (40)
"We have a family of 10 and this house was perfect for us. There was entertainment for all ages. Large areas for everyone to gather but also gave everyone their own space. Loved watching movies while swimming in the pool. Host was excellent to work with and process was easy. "
Amazing Five Bedroom Milwaukee Vacation Home!!

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

10.0 out of 10, Exceptional, (327)
"Grant has an excellent property and was fantastic in communication! He went above and beyond for sure! "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

4 Bdrm 4 Bath Lake front Lake Sinissippi home

10.0 out of 10, Exceptional, (39)
"Great"
4 Bdrm 4 Bath Lake front Lake Sinissippi home

Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

10.0 out of 10, Exceptional, (15)
"Really great location. Excellent accommodation. Clean very well equipped easy check in and out process. Only recommendation a few more blankets for beds. I’m from Fl and was in the teens needed a few extra lol. Thank you for a great home like atmosphere we were in town for our best friends funeral. "
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

Four Gables on Green Lake- Luxury Lakefront Home w/Water Views from Every Room!

Four Gables on Green Lake- Luxury Lakefront Home w/Water Views from Every Room!

Lake Beulah - Lake Front Property Getaway!

10.0 out of 10, Exceptional, (4)
"Waterfront property in a quiet cove on one of the area's best lakes. Everything was very clean. The entire space seems newly remodeled. There are outstanding lake views from the common area and from the upstairs bedroom. There are fewer steps down to the water than many properties on this lake.We loved our stay here."
Lake Beulah - Lake Front Property Getaway!

Spacious 4-bedroom house in terrific Menomonee Falls with WiFi, AC

10.0 out of 10, Exceptional, (1)
"The host was very very nice with us quick response time extremely clean property I’d definitely book here again"
The price is AED 1,010
AED 1,536 total
includes taxes & fees
28 Jan - 29 Jan
Spacious 4-bedroom house in terrific Menomonee Falls with WiFi, AC

Modern and Convenient Waukesha Home with Hot Tub

9.4 out of 10, Exceptional, (3)
"Great rental. Clean and spacious."
The price is AED 551
AED 1,170 total
includes taxes & fees
11 Feb - 12 Feb
Modern and Convenient Waukesha Home with Hot Tub

Beautiful lakefront, Newly Remodeled Lower Level! ^^

9.8 out of 10, Exceptional, (176)
"We had a great time. We were just looking for a place to get away for a quick weekend over the holidays. We are two adults couples so we brought our dogs. Had a lovely walk each morning. We hit a few local restaurants and watched a few football games. It was just great."
Beautiful lakefront, Newly Remodeled Lower Level! ^^

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (24)
"This home is very nice. Clean, well maintained and quiet neighborhood. Nice location with plenty of stores and restaurants nearby. Highly recommended. Five Stars *****"
Beautiful Waukesha Home

Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

10.0 out of 10, Exceptional, (31)
"We loved our stay here. We wanted a quiet place to stay for an extended weekend and this was the perfect spot. My kids loved the pier, the kayaks, and the bikes. I loved the giant couch and the view! The pictures didn't show off how amazing this house really is so when I walked in I literally said "Wow!". The house had everything you could possibly need. Thank you for letting us stay at your property. We will definitely be back again. "
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

9.8 out of 10, Exceptional, (8)
"This Victorian mansion was beautiful, very spacious, decorated for Christmas, and clean. We visited other family members living in the Pewaukee/Madison area for Christmas. The host was very friendly and willing to answer any questions. Checking in was down to the wire though, as there were other guests checking out while we were waiting to check in. We literally received the check in code while we were driving up the driveway! We had some trouble with the downstairs remote because it was broken....
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

9.6 out of 10, Exceptional, (10)
"Lovely unit very clean, and great hosts!"
🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨

10.0 out of 10, Exceptional, (11)
"Great location and beautiful home. Super clean, well-stocked and looks so well-cares for!"
✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨

Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!

10.0 out of 10, Exceptional, (7)
"Great property right on Lauderdale Lakes and next door to Lauderdale landing. House was new, clean, and great for entertaining a large group. Briana was a fantastic host with lightning-quick responses. Couldn't recommend this property enough for larger groups looking to spend a few days on the lake."
Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!

W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

9.6 out of 10, Exceptional, (5)
"Home needs a few fixes, but easy to do. Overall good property . Convenient placement with lots to do and many restaurants and convenient stores for provisions. "
The price is AED 444
AED 1,014 total
includes taxes & fees
28 Jan - 29 Jan
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

Modern lake house with a double lot. The views are amazing inside and out!

10.0 out of 10, Exceptional, (19)
"Super clean and comfortable! Beautiful property! Great place for a family get together "
The price is AED 1,414
AED 2,511 total
includes taxes & fees
28 Jan - 29 Jan
Modern lake house with a double lot. The views are amazing inside and out!

NEW Sunset Lake House w/ 4 fireplaces and kids bunk room!

9.8 out of 10, Exceptional, (9)
"We had multiple generations coming from many locations to celebrate mom’s 80 birthday. This home was large enough to accommodate all 13 for meals and gatherings very comfortably. There were spaces people could chat privately and a great room for everyone! Eleven of us slept there. We would definitely come again. "
NEW Sunset Lake House w/ 4 fireplaces and kids bunk room!

Relax Near Everything in Milwaukee

10.0 out of 10, Exceptional, (37)
"The property kitchen was very well stocked with the necessary items to cook meals for our family. I appreciated the double oven. The property was comfortable and clean. Convenient location. We would stay here again. Thank you!"
Relax Near Everything in Milwaukee

Quaint & Family-Friendly Watertown Farmhouse!

10.0 out of 10, Exceptional, (12)
"We traveled out for my son's wedding. The accommodations were outstanding and helped us relax from the busyness of the rehearsal and wedding. The home was very clean, and the hostess was an absolute delight. Everything we needed for a stress-free visit was provided. The beds were very comfortable, and the home gave off a cozy vibe. I would definitely stay here again."
Quaint & Family-Friendly Watertown Farmhouse!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Oconomowoc
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Oconomowoc

Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

10.0 out of 10, Exceptional, (15)
"Really great location. Excellent accommodation. Clean very well equipped easy check in and out process. Only recommendation a few more blankets for beds. I’m from Fl and was in the teens needed a few extra lol. Thank you for a great home like atmosphere we were in town for our best friends funeral. "
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

NEW Sunset Lake House w/ 4 fireplaces and kids bunk room!

9.8 out of 10, Exceptional, (9)
"We had multiple generations coming from many locations to celebrate mom’s 80 birthday. This home was large enough to accommodate all 13 for meals and gatherings very comfortably. There were spaces people could chat privately and a great room for everyone! Eleven of us slept there. We would definitely come again. "
NEW Sunset Lake House w/ 4 fireplaces and kids bunk room!

✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨

10.0 out of 10, Exceptional, (11)
"Great location and beautiful home. Super clean, well-stocked and looks so well-cares for!"
✨Chic Retreat near Wedding Venues, Downtown & Lakes with King Bed✨
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.