Holiday Homes in Oregon

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Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Oregon holiday homes

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

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (34 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is NZ$420
includes taxes & fees
22 Nov - 23 Nov
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

2. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (48 reviews)
"Great stay! Very close to everything downtown."
United States
Garrett M.
The price is NZ$544
includes taxes & fees
16 Nov - 17 Nov
Doty ★ Walk to Everything -Hotel Quality- Downtown

3. Charming 3-bedroom house on Madison's Eastside! Close to everything!

Charming 3-bedroom house on Madison's Eastside! Close to everything!
Madison
The price is NZ$1,036
includes taxes & fees
18 Nov - 19 Nov
Charming 3-bedroom house on Madison's Eastside! Close to everything!

4. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (20 reviews)
"Everything was very nice"
United States
Anonymous traveller
The price is NZ$760
includes taxes & fees
16 Nov - 17 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

5. Vast Lake Koshkonong Views from Pier, Deck, & Home

Vast Lake Koshkonong Views from Pier, Deck, & Home
Edgerton
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$551
includes taxes & fees
16 Nov - 17 Nov
Vast Lake Koshkonong Views from Pier, Deck, & Home

6. Fireplace/Coffee/Arcade Your Cozy Escape Is Here

Fireplace/Coffee/Arcade Your Cozy Escape Is Here
Milton
10.0 out of 10, Exceptional, (24 reviews)
"Excellent place!"
United States
Roger Z.
The price is NZ$1,185
includes taxes & fees
16 Nov - 17 Nov
Fireplace/Coffee/Arcade Your Cozy Escape Is Here

7. Country retreat on a family dairy goat farm.

Country retreat on a family dairy goat farm.
Orfordville
10.0 out of 10, Exceptional, (38 reviews)
"Favorite stay ever! Got to take a tour of the farm. House was clean and beds were comfortable! Plus handmade lotions for sale!! Hostess is responsive and friendly. Had a great stay."
United States
Julene S.
The price is NZ$384
includes taxes & fees
7 Dec - 8 Dec
Country retreat on a family dairy goat farm.

8. Blue Lakeview Home

Blue Lakeview Home
Edgerton
The price is NZ$474
includes taxes & fees
15 Nov - 16 Nov
Blue Lakeview Home

9. New Luxury & Spacious House in the Heart of Janesville

New Luxury & Spacious House in the Heart of Janesville
Janesville
8.8 out of 10, Excellent, (12 reviews)
"Great location for downtown Janesville "
United States
Tim M.
The price is NZ$764
includes taxes & fees
15 Nov - 16 Nov
New Luxury & Spacious House in the Heart of Janesville

10. 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
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is NZ$476
includes taxes & fees
18 Nov - 19 Nov
Escape to tranquility – your countryside haven, and at times with a horse or two

11. Edgewater Escape

Edgewater Escape
Milton
9.4 out of 10, Exceptional, (3 reviews)
"The house had a fantastic view. The open living room gave us plenty of space for relaxing as a group. Quiet area. Since we stay in many rentals our only complaint was there were no instructions for checking out, what to do with bedding, trash etc. The host never responded to my question concerning that. Hopefully we left the house as expected."
United States
Renee S.
The price is NZ$504
includes taxes & fees
17 Nov - 18 Nov
Edgewater Escape

12. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (27 reviews)
"This was the perfect size home for a holiday family get together. Nice common spaces with enough areas to go when a little alone time was needed "
United States
Steve S.
The price is NZ$963
includes taxes & fees
20 Nov - 21 Nov
Entire 3 Bedroom with Fireplace - sleeps 12
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.

Learn more about Oregon

Enjoy peaceful walks along the Oregon Ice Age Trail while watching for local wildlife in this charming small town. Anderson Farm County Park offers seasonal festivals, while nearby Madison's Capitol Square hosts Saturday farmers markets with Wisconsin cheeses you can't find elsewhere.

A cityscape with a prominent domed building, a calm body of water reflecting the skyline, and a row of trees lining the waterfront.