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Aug 15 - Aug 17
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Browse Select Oregon Vacation Homes

One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Saddleback building features a brick facade and multiple windows on each floor.

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (27)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is CA $384
CA $507 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Relax in this serene room with a high ceiling, ceiling fan, and large window offering a view of the backyard and deck.

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (61)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Two-story house with a garage on the ground floor, surrounded by a well-maintained lawn and stone wall.

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

10.0 out of 10, Exceptional, (14)
"I had the pleasure of spending a short weekend at The Earthhouse BnB in Mt. Horeb, and it was absolutely wonderful! The property is tucked away in a serene, peaceful location that provided the perfect escape from the hustle and bustle of everyday life. The BnB itself is charming and cozy, with unique touches that made it feel like a true home away from home."
The price is CA $142
CA $255 total
includes taxes & fees
Aug 24 - Aug 25
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
ONE OF A KIND vacation rental with a view
Stylish building surrounded by lush greenery, featuring a glass facade and brick architecture.

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view
YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS
Relax by the serene lake with a fire pit and wooden dock, surrounded by lush greenery.

YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS

9.8 out of 10, Exceptional, (162)
"Loved the lofted ceilings! Had everything we needed, including firewood. Can’t wait to come back"
YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Enjoy cooking in this kitchen with a large island and windows offering a view of the outdoors.

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (7)
"We loved everything about this property. Would definitely stay there again."
The price is CA $480
CA $634 total
includes taxes & fees
Sep 1 - Sep 2
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio

Private Pool - HOT TUB - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (1)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
Private Pool - HOT TUB - Sauna - Game Room - Pets
Two bedroom suite with city views in the heart of downtown Madison
Enjoy a meal at the kitchen island with a cutting board, or relax in the adjacent seating area with a view of the city skyline.

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (33)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is CA $453
CA $598 total
includes taxes & fees
Sep 1 - Sep 2
Two bedroom suite with city views in the heart of downtown Madison
One Bedroom King with Den with views of the heart of downtown.
Standing tall with a historic central dome, this building offers a glimpse into the past.

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (23)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is CA $370
CA $489 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with Den with views of the heart of downtown.
Doty ★ Walk to Everything -Hotel Quality- Downtown
Enjoy cooking in this well-equipped kitchen with a dishwasher, oven, and gas stove.

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown
Paoli Den - Newly Remodeled!
Enjoy cooking in this well-equipped kitchen with a microwave, coffee maker, and kettle.

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (23)
"Prefect"
Paoli Den - Newly Remodeled!
Beautifully updated home close to downtown New Glarus
Relax on the inviting front porch with Adirondack chairs, surrounded by a serene garden and a tranquil water feature.

Beautifully updated home close to downtown New Glarus

10.0 out of 10, Exceptional, (58)
"It was so good to come back to a clean and cozy house each evening after spending the day at the World Dairy Expo."
Beautifully updated home close to downtown New Glarus
Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL
Enjoy al fresco dining with a view of the surrounding landscape from this outdoor dining area featuring a table and chairs.

Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL

10.0 out of 10, Exceptional, (32)
"Peaceful, quiet"
Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL
Waterfront - Hot Tub - Sauna - Game Room - Pets
Relax on the deck overlooking the calm water, where you can soak in the hot tub or enjoy a drink at the bar.

Waterfront - Hot Tub - Sauna - Game Room - Pets

9.0 out of 10, Wonderful, (2)
"This rental made for the perfect group weekend getaway. From the great shuffleboard table to the vintage arcade games like NBA Jam, this place was on fire! The beautiful view of the wide river from the hot tub was so tranquil a member of our group asked what lake we were on. It’s the perfect distance from Madison and Chicago that you feel like you’ve truly gotten away, but close enough that lots of activities feel easily accessible. The house was clean and well stocked with everything needed to...
The price is CA $766
CA $1,621 total
includes taxes & fees
Aug 11 - Aug 12
Waterfront - Hot Tub - Sauna - Game Room - Pets
Escape to tranquility – your countryside haven, and at times with a horse or two
Relax on the patio with a sofa and two chairs, shaded by a covered area.

Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Plan your reunion/gathering now in beautiful rural South Central Wisconsin
Enjoy a relaxing moment on the covered porch with a seating area and comfortable sofas.

Plan your reunion/gathering now in beautiful rural South Central Wisconsin

10.0 out of 10, Exceptional, (162)
"Oak House is a unique property ideally suited for family gatherings - this was our fourth stay. The house is roomy, well appointed, and decorated for the holidays. It also has access to nature trails for daily walks. The location has quiet privacy with quick access to activities in Madison. The property manager Rachel is very responsive. We highly recommend a stay here. "
Plan your reunion/gathering now in beautiful rural South Central Wisconsin
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Relax in a cozy space with a neatly made bed, wooden headboard, and two bedside tables.

Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

10.0 out of 10, Exceptional, (33)
"We had a great time being close to the lake. Everything in the house was very charming and comfortable. Would stay again for sure!"
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Charming 4-bedroom Lake house on Lake Ripley in Cambridge
Relax in this inviting living room with a sofa, coffee table, and comfortable seating area overlooking a serene landscape.

Charming 4-bedroom Lake house on Lake Ripley in Cambridge

10.0 out of 10, Exceptional, (13)
"Really enjoyed the space "
Charming 4-bedroom Lake house on Lake Ripley in Cambridge
Bears Den: Year-round Comfortable 4-bdrm house on Lake Ripley in Cambridge WI
Stunning two-story home with a central chimney, front porch, and beautifully manicured lawn.

Bears Den: Year-round Comfortable 4-bdrm house on Lake Ripley in Cambridge WI

2.0 star property
9.8 out of 10, Exceptional, (10)
"It was a nice accommodating place with easy to use immenaties. "
Bears Den: Year-round Comfortable 4-bdrm house on Lake Ripley in Cambridge WI
Spacious & Modern Home w/ Deck in Oregon!
Enjoy cooking in this kitchen with a central island, stainless steel sink, microwave, and gas range.

Spacious & Modern Home w/ Deck in Oregon!

7.0 out of 10, Good, (2)
"Awesome...very clean property.Plenty of space for eight people...Quiet neighborhood"
Spacious & Modern Home w/ Deck in Oregon!
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.
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Top Oregon Hotel Reviews

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"The most comfortable beds EVER. I even took a picture of the tags so I can get the same exact one! Love this hotel! My rant has stayed there at least 10 times and will keep coming back!"
Stephanie 2-night trip
Posted 11 hours ago
The Madison Concourse Hotel and Governor's Club