Photo by Amber Petersen

Holiday Homes in Sherwood

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Featured Holiday Homes in Sherwood

Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

9.6 out of 10, Exceptional, (66)
"I loved staying here. I am a florist and was traveling for a wedding that took place downtown Portland, and this place was so conveniently close. Max 15min drive away. The neighborhood was quiet and beautiful so you were close to big city, but had quiet suburbs living as well. Can’t recommend this place enough. The host was also really easy to contact, had no issues whatsoever. Would love to stay again!! "
The price is NZ$589
includes taxes & fees
24 Nov - 25 Nov
Gem in Milwaukie 2 bedroom - 2 Bathroom - Huge yard

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 NZ$594
includes taxes & fees
4 Dec - 5 Dec
Designer Owned House on Vibrant Williams Avenue near Mississippi

Secluded large home. Wooded setting. Easy commute to downtown.

9.4 out of 10, Exceptional, (85)
"We had an enjoyable stay at this charming home! I recommend this home to all, especially if you have a large group as there is plenty of space!!! Secluded, yet within 15-20 mins to anything you need. The views kick off during the drive in. Our adult kids loved the different floors, especially the basement! Views are gorgeous at any time of day or night. Star gazing is amazing in the back deck too. Lots of sunlight through the windows, yet not a bit cold. The home is very cozy! Open a...
Secluded large home. Wooded setting. Easy commute to downtown.

Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd

10.0 out of 10, Exceptional, (149)
"We loved the neighborhood and our host had provided lots of local information and was accessible. Convenient location, walk-able with scenic views. "
Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd

Exquisite Historic Suite Close to Downtown 14-21673

10.0 out of 10, Exceptional, (461)
"Beautiful location and really nice host"
The price is NZ$315
includes taxes & fees
4 Dec - 5 Dec
Exquisite Historic Suite Close to Downtown 14-21673

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 NZ$589
includes taxes & fees
1 Dec - 2 Dec
Large Cozy Home

Picturesque Retreat On 80 Acres of Organic Farmland, Farm Animals Galore In Middle of Wine Country

10.0 out of 10, Exceptional, (61)
"Fabulous!! Immaculate! Inviting! Cozy! Gorgeous!"
Picturesque Retreat On 80 Acres of Organic Farmland, Farm Animals Galore In Middle of Wine Country

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

Picturesque Panoramic Vineyard Views From Home and Hot Tub, Pet Friendly, Private, Fire-Pit, BBQ

10.0 out of 10, Exceptional, (38)
"Very comfortable and beautiful house, view and surroundings. Perfect location for meeting up with friends for local wine tasting. Thank you "
Picturesque Panoramic Vineyard Views From Home and Hot Tub, Pet Friendly, Private, Fire-Pit, BBQ

Overlook Cottage, Upscale 2 bedroom and 2 bath

10.0 out of 10, Exceptional, (62)
"So comfortable. Great value. Walkable,safe neighborhood. Loved the layout of the cottage. 1 bed and bath upstairs and 1 down. Would stay again. Easy checklist for leaving. "
Overlook Cottage, Upscale 2 bedroom and 2 bath

Phenomenal Single Level Home Featuring Incredible Outdoor Golf Option w/ Gazebo, Fire-Pit, and Patio

9.2 out of 10, Wonderful, (47)
"This was a great house for our little getaway. We needed a quiet place for us to watch movies, play cards, and hang out together and this was exactly what we needed. The fully fenced yard was nice so my dog could explore the latest smells whenever he wanted."
Phenomenal Single Level Home Featuring Incredible Outdoor Golf Option w/ Gazebo, Fire-Pit, and Patio

Bright and Delightful Renovation, Single Level, Fenced Backyard, 3 Blocks to MAX, 25 Min to Portland

9.6 out of 10, Exceptional, (36)
"It was a cute, family-friendly place, and had all of what we could possibly need for our trip. This was a great home away from home while visiting family."
Bright and Delightful Renovation, Single Level, Fenced Backyard, 3 Blocks to MAX, 25 Min to Portland

PNW Downtown Hobbit Home - Detached game-room & Outdoor pizza oven!

10.0 out of 10, Exceptional, (4)
"Lovely décor, very thoughtful amenities for travelers. A !"
The price is NZ$491
includes taxes & fees
25 Nov - 26 Nov
PNW Downtown Hobbit Home - Detached game-room & Outdoor pizza oven!

Dog-friendly Beaumont Craftsman with covered porch & yard - walk to bars/dining

8.2 out of 10, Very good, (11)
"Great location, short walk to food and coffee spots. Only 10 min drive to the city."
Dog-friendly Beaumont Craftsman with covered porch & yard - walk to bars/dining

The Magic House, Walk Score 93!

9.6 out of 10, Exceptional, (40)
"I run a small nonprofit and we come together for only one in person board meeting a year. I rented the Magic House because it had enough bedrooms and we could afford it. We were all comfortable in the beds (tho traffic noise was disturbing in rooms that faced Cesar Chavez). Well supplied kitchen. Great bathrooms. A big enough table. Interesting art. It was great to walk together to cafes. A good experience. "
The price is NZ$857
includes taxes & fees
1 Dec - 2 Dec
The Magic House, Walk Score 93!

Magnificent Home on Banks of the Willamette River, Hot Tub, Fire-Pit, Cornhole, 9 Miles to Downtown

10.0 out of 10, Exceptional, (34)
"I wish I could retire here and sit in the chairs in front of the windows to watch the bald eagles, birds and geese all day! Beautiful home with comfortable spaces for our whole family to enjoy my husband's birthday."
Magnificent Home on Banks of the Willamette River, Hot Tub, Fire-Pit, Cornhole, 9 Miles to Downtown

Fantastic Bungalow with Hot tub, Decks, Close to everything, modern and clean

9.4 out of 10, Exceptional, (23)
"WE HAD OUR DAUGHTERS WEDDING AT THE LAURELHURST CLUB. LOVELY VENUE & THE STAFF AT THE CLUB WERE SUPERB"
Fantastic Bungalow with Hot tub, Decks, Close to everything, modern and clean

Comfortable Elegance in the Heart of Downtown Newberg

10.0 out of 10, Exceptional, (160)
"We cannot say enough nice things about this property. Every possible thing you could want has been thought of and is readily available. Leigh is wonderful and gave a great run down of the house. She said that if we needed anything, to just ask, but we truly never needed to bother her. A great place to relax between wine tastings. Hang out in the hot tub, or relax by a fire in the living room. Just wonderful ambience no matter where you decide to hang out. Should we even end up staying new...
Comfortable Elegance in the Heart of Downtown Newberg

Splendid Location, Single Level, Pet Friendly, Huge Fenced Yard, BBQ, Games, Next to School Fields

10.0 out of 10, Exceptional, (19)
"Everything about the Arrington Retreat was delightful!! I grew up in Hillsboro and was home visiting family. This was a perfect place for our "base camp". I will definitely stay here again the next time we are in town"
Splendid Location, Single Level, Pet Friendly, Huge Fenced Yard, BBQ, Games, Next to School Fields

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
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 Sherwood

Larkspur Landing Extended Stay Suites Hillsboro

3.0 star property
8.2 out of 10, Very good, (1689)
"Nice continental breakfast"
The price is NZ$187
includes taxes & fees
26 Nov - 27 Nov
Larkspur Landing Extended Stay Suites Hillsboro

Inn at Northrup Station

3.0 star property
9.4 out of 10, Exceptional, (1964)
"My wife and I have stayed at The Inn at Northrup Station a number of times. The decor is fun and funky. The rooms are spacious having both a sitting area and a full kitchen. We love the location being close to 23rd (and 21st) with numerous stores and restaurants. With the cable car stop right outside the hotel, transportation (free) to downtown is easy and convenient. One area that could use an upgrade is the breakfast. It is very carb heavy with nothing cooked fresh. Even the waffle maker,...
The price is NZ$276
includes taxes & fees
24 Nov - 25 Nov
Inn at Northrup Station

World Renowned Roloff Farms, Billiards, Game Room, On Acres of Farmland

10.0 out of 10, Exceptional, (22)
"Beautiful home, perfect for adult getaway or family getaway. Location is picturesque and so relaxing. An A+ experience"
World Renowned Roloff Farms, Billiards, Game Room, On Acres of Farmland
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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