Photo by Michelle Finseth

Holiday Homes in Clackamas

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Featured Holiday Homes in Clackamas

Designer Owned House on Vibrant Williams Avenue near Mississippi

10.0 out of 10, Exceptional, (169)
"North central Portland location for close access to airport. Functional and well thought out home layout. Great for small family. "
The price is AU$539
includes taxes & fees
2 Dec - 3 Dec
Designer Owned House on Vibrant Williams Avenue near Mississippi

Large Cozy Home

9.8 out of 10, Exceptional, (13)
"This VRBO is a great property that is well maintained and has a very comfortable floor plan. Location is near 82nd and Foster, with plenty of shops and restaurants nearby. Highly recommend staying at this VRBO."
The price is AU$671
includes taxes & fees
1 Dec - 2 Dec
Large Cozy Home

Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row

10.0 out of 10, Exceptional, (276)
"My stay here was delightful. The home has everything you need for a weekend away or to make this your home base for a bit. The kitchen has everything, and the spaces are well thought out. The owner has made many special touches to ensure your stay is comfortable and easy. I look forward to staying again when I am back in PDX. "
Location, style and space! - Midcentury Modern Home - Steps from Restaurant Row

Modern Updated Home, Game Room, Open Layout, Family Friendly, Near Intel & Nike 5 Min Walk to MAX

9.6 out of 10, Exceptional, (63)
"It was a great experience "
Modern Updated Home, Game Room, Open Layout, Family Friendly, Near Intel & Nike 5 Min Walk to MAX

Watts Landing - a city escape

9.8 out of 10, Exceptional, (13)
"What a cute and relaxing house! No complaints. It was a perfect location for both relaxing at the house and for being able to walk or drive to plenty of things around. The kitchen had all the essentials, the beds were comfortable, and we especially appreciated the plants in the living space and the noise machines provided in the bedrooms. Will definitely consider staying here again!"
Watts Landing - a city escape

Sleek Townhome w/ Patio - Walk to Amazing Restaurants, Breweries, Trails & Shops

9.2 out of 10, Wonderful, (135)
"Place was very nice but there were a couple of things that could have been better. First, the lighting is not as bright as shown. All the lights are yellow & not very bright at all. The ceiling fan light in one of the rooms didn’t even work. There were some crumbs left in the couch and there was a nasty stain on one of the bed blankets. One of the bedrooms also didn’t lock. The walls are super thin so we could hear the neighbors when they were really loud at night. Other than that, it was a cool...
The price is AU$592
includes taxes & fees
4 Dec - 5 Dec
Sleek Townhome w/ Patio - Walk to Amazing Restaurants, Breweries, Trails & Shops

Excellent Location, Close to Parks, Groceries, Single Level Detached Retreat, 15 Minutes to Portland

9.8 out of 10, Exceptional, (62)
"Very convenient, clean, well taken care of, comfortable, quiet, well appointed guest house. Will stay again when visiting our daughter in the area. Thank you for offering such a great place to stay. "
Excellent Location, Close to Parks, Groceries, Single Level Detached Retreat, 15 Minutes to Portland

1.2M New Luxury Home, Hot Tub, 4 King Beds, 2 in-Suites, Fast Wifi

10.0 out of 10, Exceptional, (35)
"In town with my 81 year old mom and her 3 other siblings to celebrate their sister's birthday. This house was perfect for our visit. Everyone had a room and the open area for kitchen and living area made our evenings very enjoyable. House is well stocked with kitchen staples and bathroom/shower needs. Outside area was relaxing and we enjoyed the fire and the hottub. "
1.2M New Luxury Home, Hot Tub, 4 King Beds, 2 in-Suites, Fast Wifi

Spacious Hillsboro Home ~ 18 Mi to Portland!

10.0 out of 10, Exceptional, (14)
"We fell in love with this property. I had a very welcoming feeling we all felt at home. The landscaping was so beautifully done. House was perfect. Hosts were super friendly and helpful. Definitely want to stay there again next time we are in the area."
Spacious Hillsboro Home ~ 18 Mi to Portland!

Beautiful Quiet Farm House for Families to Enjoy

9.4 out of 10, Exceptional, (3)
"Property was very clean and exactly as advertised. Owners were extremely kind and gracious to allow us to have our 180lb dog stay with us. Very appreciative"
The price is AU$799
includes taxes & fees
26 Dec - 27 Dec
Beautiful Quiet Farm House for Families to Enjoy

Enjoy this home away from home

9.8 out of 10, Exceptional, (8)
"It felt like home. The property line in back is a beautiful park. Everything about this place was awesome"
Enjoy this home away from home

High End New Estate Home in Lake Oswego. Private suite on 1st level w/o stairs.

10.0 out of 10, Exceptional, (7)
"Perfect stay! Very comfortable!"
The price is AU$1,766
includes taxes & fees
27 Dec - 28 Dec
High End New Estate Home in Lake Oswego. Private suite on 1st level w/o stairs.

#StayinMyDistrict Sellwood Coco Rose Retreat

2.0 star property
10.0 out of 10, Exceptional, (16)
"Exactly what we needed for a short visit with our son in Sellwood. We especially liked that it had a couch and chair for relaxing inside."
The price is AU$319
includes taxes & fees
3 Dec - 4 Dec
#StayinMyDistrict Sellwood Coco Rose Retreat

Mid-century modern home with pool, WiFi, BBQ grill, patio, and fireplace

2.0 star property
Mid-century modern home with pool, WiFi, BBQ grill, patio, and fireplace

Fantastic 1920's English Cottage /w Patio, Seconds from Performing Arts, Restaurants, Bars, Shopping

9.4 out of 10, Exceptional, (6)
"Such a charming old cottage! The couches and beds were so comfortable. We loved the location- right off the Main Street through Multnomah Village. Lots of stores and restaurants within a 10 minute walk. Also a short drive into downtown Portland!"
Fantastic 1920's English Cottage /w Patio, Seconds from Performing Arts, Restaurants, Bars, Shopping

HIGHLY sought, HIGHLY ranked, spacious 4 bdrm home with unbeatable location

HIGHLY sought, HIGHLY ranked, spacious 4 bdrm home with unbeatable location

Private Vineyard Lodge retreat on 5 acres

2.0 star property
10.0 out of 10, Exceptional, (1)
"As a group we feel it should get a rating of 15 out of 10. It was beautiful, clean, and more than even expected. Fresh bread that was truly amazing. Would highly recommend! "
Private Vineyard Lodge retreat on 5 acres

Live the Dream on the Beautiful Willamette River

9.4 out of 10, Exceptional, (196)
"The property has an amazing outdoor area to enjoy! The house is well stocked. The only thing a little odd is the third bed is in the living area, but there is a door that closes off. would stay here again Sara is very accommodating"
Live the Dream on the Beautiful Willamette River

Cedar Mill Getaway

9.8 out of 10, Exceptional, (105)
"Our Stay (6 of us) was too short at Cedar Mill. I regret not taking the time to enjoy the outdoor section of the home. It was a relaxing stay, loved the interior/exterior of the home. Didn’t have to contact the owner for anything, the home is nicely supplied/clean and met expectations. If coming to Portland, this home is based in a quiet area, definitely coming back! "
The price is AU$291
includes taxes & fees
1 Dec - 2 Dec
Cedar Mill Getaway

NEW! - Bright Modern Entire Unit KING BED!

9.6 out of 10, Exceptional, (13)
"This space is very nice and clean. The first night we had issues with a parking space, but the owner quickly rectified that and we had a great stay and would definitely recommend this space if you are traveling to the Portland area"
NEW! - Bright Modern Entire Unit 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.
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Other property types in Clackamas

Inn at Northrup Station

3.0 star property
9.4 out of 10, Exceptional, (1964)
"All around fantastic. Would stay again and again !"
The price is AU$266
includes taxes & fees
9 Dec - 10 Dec
Inn at Northrup Station

Modern Chateau on private hillside with breathtaking views of the Columbia River

10.0 out of 10, Exceptional, (11)
"Enjoyed the stay very much. Would have been perfect if it had more window coverings. "
Modern Chateau on private hillside with breathtaking views of the Columbia River

Panoramic Riverside and Lush Forests Views, Pet Friendly, New Décor, Steps Away From Dockside

10.0 out of 10, Exceptional, (38)
"Beautiful property and views. Quiet and serene. Home was clean and comfortable with fully stocked kitchen and great amenities. We had a great stay!"
Panoramic Riverside and Lush Forests Views, Pet Friendly, New Décor, Steps Away From Dockside
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.