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Search results; Over 1,000 homes in Sherwood

Guest favorite
Villa in Sherwood
Wine🍷 country ⭐️ 180° view ⭐️ Fitness & Game room!
3 bedrooms, 3 beds, 2 private baths
Aug 15 – 20
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4.9 out of 5 average rating, 31 reviews
Top guest favorite
Home in Sherwood
Old Town Retreat - Best place in Old Town Sherwood
3 bedrooms, 6 beds, 2.5 baths
Sep 8 – 13
4.99 out of 5 average rating, 190 reviews
Top guest favorite
Guest suite in Sherwood
Sherwood Hollow- Senior discount (60+) $88/night
1 bedroom, 2 beds, 1 bath
Oct 28 – Nov 2
4.98 out of 5 average rating, 335 reviews
Top guest favorite
Home in Sherwood
20acre/8500sqft/Sauna/GameRm/Bunks/Theater/SportCt
8 bedrooms, 14 beds, 7.5 baths
Oct 24 – 29
5.0 out of 5 average rating, 8 reviews
Top guest favorite
Barn in Sherwood
Rustic Barn | Country Getaway
2 beds, 1 bath
Sep 21 – 26
4.98 out of 5 average rating, 250 reviews
Top guest favorite
Cottage in Sherwood
Charming cottage in a peaceful garden setting.
1 bedroom, 2 beds, 1 bath
Aug 28 – Sep 2
4.96 out of 5 average rating, 273 reviews
Top guest favorite
Guest suite in Sherwood
Bacchus Fields - Oregon Wine Country Studio
1 queen bed, 1 bath
Sep 14 – 19
4.98 out of 5 average rating, 146 reviews
Top guest favorite
Guesthouse in Sherwood
Wine Country Casita: Private Guesthouse/Nice Views
1 bedroom, 2 queen beds, 1 bath
Aug 30 – Sep 4
5.0 out of 5 average rating, 32 reviews
Top guest favorite
Barn in Sherwood
Tree Top Studio- *Brand New* in Wine Country
1 bedroom, 2 beds, 1 bath
Aug 29 – Sep 3
4.99 out of 5 average rating, 158 reviews
Top guest favorite
Home in Sherwood
Chateau Chardonnay:Tuscan home in NW wine country
3 bedrooms, 5 beds, 3.5 baths
Sep 14 – 19
4.95 out of 5 average rating, 167 reviews
Top guest favorite
Home in Sherwood
Wine Country • Sunroom Hot Tub • Walk Downtown
5 bedrooms, 6 beds, 3 baths
Sep 23 – 28
4.97 out of 5 average rating, 58 reviews
Top guest favorite
Cottage in Sherwood
Oregon Wine Country Retreat: Sip & Dine Outside
1 bedroom, 1 king bed, 1 bath
Sep 8 – 13
5.0 out of 5 average rating, 20 reviews
Guest favorite
Home in Sherwood
Wine Country Horse Farm Cabin Near Wineries!
4 bedrooms, 8 beds, 2 baths
Aug 29 – Sep 3
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Sherwood
OR Wine Country Get Away
3 bedrooms, 4 beds, 1 bath
Aug 21 – 26
5.0 out of 5 average rating, 90 reviews
Farm stay in Sherwood
Vista Ridge Retreat | 5Acres, Game Room & Fire Pit
3 bedrooms, 6 beds, 1 bath
Aug 16 – 21
5.0 out of 5 average rating, 3 reviews
Guest favorite
Cottage in Beaverton
Cozy Cooper Mtn Cottage
2 bedrooms, 2 queen beds, 1 bath
Oct 5 – 10
4.93 out of 5 average rating, 151 reviews
Top guest favorite
Farm stay in Sherwood
Ariniello Vineyard - Private 2 Bedroom Suite
2 bedrooms, 2 beds, 1 bath
Sep 8 – 13
4.89 out of 5 average rating, 211 reviews
Top guest favorite
Cabin in Yamhill
The Roost at Roots Vineyard
1 bedroom, 1 double bed, 1 bath
Sep 7 – 12
5.0 out of 5 average rating, 15 reviews
Top guest favorite
Tiny home in Beaverton
Beaverton Vintage Tiny Home
1 bedroom, 2 beds, 1 bath
Sep 20 – 25
4.96 out of 5 average rating, 236 reviews