A landscape with a dense forest and a cloudy sky.

Holiday Homes in Sherwood

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Sherwood holiday homes

A covered outdoor area with a hot tub, seating, and a sign indicating towels are available.

1. Luxury Wine Retreat • Spa Sunroom • Walk Downtown

Luxury Wine Retreat • Spa Sunroom • Walk Downtown
Sherwood - Tualatin South
9.2 out of 10, Wonderful, (10 reviews)
"Very spacious and comfortable - beautiful place with lots of nice touches. My family came to town for a funeral and it was so nice to have a home base as nice as this to come back to each day. The host is very kind and responsive. 2 block walk to a great little Mexican cantina too. "
United States
Sally S.
The price is NZ$3,768
includes taxes & fees
14 Oct - 15 Oct
Luxury Wine Retreat • Spa Sunroom • Walk Downtown
A rustic outdoor seating area with benches and picnic tables, surrounded by dense forest.

2. Creekside Haven

Creekside Haven
Wilsonville
10.0 out of 10, Exceptional, (75 reviews)
"Very comfortable ,had everything we needed. Wish we could have stayed longer."
United States
Eric S.
The price is NZ$374
includes taxes & fees
16 Sept - 17 Sept
Creekside Haven
A deck with outdoor furniture, a grill, and a view of tall trees.

3. Private and Quiet Couples Escape, New Construction, Décor, and Furnishings, Gorgeous Deck & BBQ

Private and Quiet Couples Escape, New Construction, Décor, and Furnishings, Gorgeous Deck & BBQ
Ladd Hill
9.4 out of 10, Exceptional, (32 reviews)
"Nice spot centrally located in Willamette Valley wine country. While it’s just tucked in off a main road, it remained quiet and felt restful. We appreciated the electric fireplace."
United States
Carrie D.
The price is NZ$691
includes taxes & fees
16 Sept - 17 Sept
Private and Quiet Couples Escape, New Construction, Décor, and Furnishings, Gorgeous Deck & BBQ
A living room with a sofa, a coffee table, and a dining area with chairs. There is a plant on a side table and a painting on the wall.

4. Spectacular Choice: Sleeps 6, Your Dog Welcome Too

Spectacular Choice: Sleeps 6, Your Dog Welcome Too
Bull Mountain
9.6 out of 10, Exceptional, (56 reviews)
"Great location"
United States
norm s.
The price is NZ$510
includes taxes & fees
23 Sept - 24 Sept
Spectacular Choice: Sleeps 6, Your Dog Welcome Too
A modern kitchen with white cabinetry, a central island with stools, a dishwasher, and a large window with blinds.

5. Newberg Getaway - Wineries, Weddings, GFU

Newberg Getaway - Wineries, Weddings, GFU
Newberg
9.8 out of 10, Exceptional, (52 reviews)
"Great stay at Newberg!"
United States
Billy W.
The price is NZ$567
includes taxes & fees
20 Sept - 21 Sept
Newberg Getaway - Wineries, Weddings, GFU
A modern kitchen with white cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

6. Granny Flat in leafy SW Portland

Granny Flat in leafy SW Portland
Southwest Portland
9.4 out of 10, Exceptional, (29 reviews)
"Literally enjoyed the place, the host were extremely good at communicating and very understanding. Definitely a 9.5/10"
United States
Daquarious
The price is NZ$228
includes taxes & fees
16 Sept - 17 Sept
Granny Flat in leafy SW Portland
A modern hotel interior with mirrored walls, multiple beds with pillows, and a glass floor.

7. The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors

The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors
Lake Oswego
9.8 out of 10, Exceptional, (22 reviews)
"Great location and super fun house. We really enjoyed it"
United States
Lauren B.
The price is NZ$524
includes taxes & fees
17 Sept - 18 Sept
The OMG House that will BLOW YOUR MIND with Unbelievable Cats n Mirrors
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a red kettle on the stove.

8. #StayinMyDistrict Modern Mid-Century Retreat

#StayinMyDistrict Modern Mid-Century Retreat
Vose
8.8 out of 10, Excellent, (21 reviews)
"Perfect location in downtown Beaverton. You can walk everywhere from this house. Yard was nice, the house was comfortable, especially the bed. I didn't cook while there but the kitchen seemed well stocked. I would stay here again for sure."
United States
Aileen Y.
The price is NZ$668
includes taxes & fees
16 Sept - 17 Sept
#StayinMyDistrict Modern Mid-Century Retreat
A modern kitchen with white cabinetry, a central island, and a dining area with a wooden table and chairs.

9. Entertainment Haven / Pool Table

Entertainment Haven / Pool Table
Garden Home-Whitford
9.8 out of 10, Exceptional, (9 reviews)
"House was comfortable, roomy and great location "
United States
Jim F.
The price is NZ$1,014
includes taxes & fees
29 Sept - 30 Sept
Entertainment Haven / Pool Table
A house with a patio area featuring two green chairs and a table, a fire pit, and a bicycle parked outside.

10. #StayInMyDistrict Lake Oswego Honey Bee Cottage

#StayInMyDistrict Lake Oswego Honey Bee Cottage
First Addition
9.6 out of 10, Exceptional, (42 reviews)
"Located in a quiet, enjoyable neighborhood of Lake Oswego. Walking to shops and restaurants, or hiking in Tryon Creek is easily accessible. Property was clean and necessary items provided. I very much enjoyed my stay."
United States
Carrie
The price is NZ$572
includes taxes & fees
20 Sept - 21 Sept
#StayInMyDistrict Lake Oswego Honey Bee Cottage
A backyard with a wooden deck, a table with chairs, a large umbrella, and a fire pit.

11. 2 King Beds, Quiet Neighborhood, Near It All

2 King Beds, Quiet Neighborhood, Near It All
Bull Mountain
10.0 out of 10, Exceptional, (59 reviews)
"Third time we have stayed at this property. That says it all. Nice amenities and convenient location."
United States
Anonymous traveller
The price is NZ$1,159
includes taxes & fees
30 Sept - 1 Oct
2 King Beds, Quiet Neighborhood, Near It All

12. Guest Suite with WiFi, AC, streaming

Guest Suite with WiFi, AC, streaming
Southwest Portland
9.0 out of 10, Wonderful, (21 reviews)
"Nice place for us to stay while visiting family in the area. "
United States
Chris W.
The price is NZ$439
includes taxes & fees
17 Sept - 18 Sept
Guest Suite with WiFi, AC, streaming
A wooden cabin with a deck overlooking a forested stream.

13. Sasquatch's Tiny Treehouse on creek - old growth forest in Portland - ADVENTURE!

Sasquatch's Tiny Treehouse on creek - old growth forest in Portland - ADVENTURE!
Cedar Hills
9.2 out of 10, Wonderful, (9 reviews)
"Unfortunately, our reservation was double-booked. When we arrived, the cabin was already occupied by another guest. We were unable to reach anyone from either the property or Vrbo who could help at the time, so we had to spend part of our vacation finding another place to stay. Communication was difficult throughout the process. We booked through Expedia, and because the reservation was processed through Vrbo, we were unable to receive messages or check-in instructions. In the end, that...
United States
Ashley
The price is NZ$366
includes taxes & fees
17 Sept - 18 Sept
Sasquatch's Tiny Treehouse on creek - old growth forest in Portland - ADVENTURE!
A wooden deck with a glass door leading to a forested area.

14. Oregon Jade- West Linn 2 rooms, EV charger, fire pit, forest view, deer glazing

Oregon Jade- West Linn 2 rooms, EV charger, fire pit, forest view, deer glazing
Rosemont Summit
8.4 out of 10, Very good, (26 reviews)
"Nice, clean place in a good neighborhood."
United States
Andrew M.
The price is NZ$400
includes taxes & fees
29 Sept - 30 Sept
Oregon Jade- West Linn 2 rooms, EV charger, fire pit, forest view, deer glazing
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

15. Spacious 5BR Beaverton Home, Game Room, Near Portland

Spacious 5BR Beaverton Home, Game Room, Near Portland
Aloha
10.0 out of 10, Exceptional, (22 reviews)
"Perfect for our two families. Would stay here again!"
United States
Angie R.
The price is NZ$1,201
includes taxes & fees
20 Sept - 21 Sept
Spacious 5BR Beaverton Home, Game Room, Near Portland
A hot tub with two glasses and a bottle of champagne, set against a twilight cityscape.

16. Parrett Mtn Estate: Hot Tub, Sauna, Cold Plunge, Fire Pit, Vine & Valley Views

Parrett Mtn Estate: Hot Tub, Sauna, Cold Plunge, Fire Pit, Vine & Valley Views
Newberg
10.0 out of 10, Exceptional, (137 reviews)
"Amazing property on amazing land with views that go on forever! Will be staying here again!"
United States
Bradley L.
The price is NZ$1,849
includes taxes & fees
7 Oct - 8 Oct
Parrett Mtn Estate: Hot Tub, Sauna, Cold Plunge, Fire Pit, Vine & Valley Views
A living room with a sofa, a coffee table, a TV, and a desk.

17. 2 bedroom / 1 bath entire house across from the food trucks of the Aloha mall!

2 bedroom / 1 bath entire house across from the food trucks of the Aloha mall!
Beaverton
9.2 out of 10, Wonderful, (28 reviews)
"I will never stay anywhere else in the Portland area!"
United States
Joshua S.
The price is NZ$661
includes taxes & fees
13 Oct - 14 Oct
2 bedroom / 1 bath entire house across from the food trucks of the Aloha mall!
A spacious living room with a fireplace, a dining area with a wooden cabinet, and a large window offering a view of greenery.

18. Spacious SW Portland home with Fire Pit

Spacious SW Portland home with Fire Pit
Portland
9.0 out of 10, Wonderful, (13 reviews)
"This was a cute, clean property with thoughtful amenities! Thank you for the great stay!"
United States
Sarah B.
The price is NZ$607
includes taxes & fees
21 Sept - 22 Sept
Spacious SW Portland home with Fire Pit
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with white chairs and a wooden table.

19. Near Brickhaus Coffee+Dos Hermanos Bakery w/Board Games-Coffee Maker+Microwave

Near Brickhaus Coffee+Dos Hermanos Bakery w/Board Games-Coffee Maker+Microwave
Five Oaks
9.0 out of 10, Wonderful, (14 reviews)
"The house was perfect for my family and I for a few days. It had everything we needed. The beds were super comfy!"
United States
Cassandra F.
The price is NZ$849
includes taxes & fees
20 Sept - 21 Sept
Near Brickhaus Coffee+Dos Hermanos Bakery w/Board Games-Coffee Maker+Microwave
A living room with a brown leather sofa, a striped armchair, a white coffee table, a flat-screen TV mounted on the wall, and a window with an umbrella outside.

20. #StayinMyDistrict Sellwood Coco Rose Retreat

#StayinMyDistrict Sellwood Coco Rose Retreat
Southeast Portland
10.0 out of 10, Exceptional, (43 reviews)
"Perfect location in the heart of Sellwood."
United States
Karen V.
The price is NZ$436
includes taxes & fees
16 Sept - 17 Sept
#StayinMyDistrict Sellwood Coco Rose Retreat
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 Sherwood Hotel Reviews

The Clyde Hotel Portland by Kasa Living

The Clyde Hotel Portland by Kasa Living

8/10 Good
"Great stay. Spacious room, cozy bed, interesting furnishings. Appreciated the tokens for coffee next door, too. City to city, Kasa is doing something right."
scott 2-night trip
Posted less than an hour ago
The Clyde Hotel Portland by Kasa Living

Find out more about Sherwood

Sherwood Holiday Homes information

Number of reviews
562
Accommodation
1033 Holiday Homes
Lowest Price
NZ$228
Highest Price
NZ$3,768