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Sherwood Holiday Rentals

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50 rentals in Sherwood.
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Camp Heaven All The Fun Of Camping Without All The Work!, holiday rental in Sherwood

Camp Heaven All The Fun Of Camping Without All The Work!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gated Property With Vineyard View Surrounded By Mountainscape, holiday rental in Sherwood

Gated Property With Vineyard View Surrounded By Mountainscape

3 bedrooms
2 bathrooms
Sleeps 9
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Lovely Sherwood Retreat w/ Yard, Walk to Old Town!, holiday rental in Sherwood

Lovely Sherwood Retreat w/ Yard, Walk to Old Town!

2 bedrooms
1 bathroom
Sleeps 4
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Carefully Restored  Wilsonville Farmhouse next to Parks & Trails, 1 Mile to I-5, holiday rental in Sherwood

Carefully Restored Wilsonville Farmhouse next to Parks & Trails, 1 Mile to I-5

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable Elegance in the Heart of Downtown Newberg, holiday rental in Sherwood

Comfortable Elegance in the Heart of Downtown Newberg

3 bedrooms
2 bathrooms
Sleeps 4
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A Handsome Newly Remodeled Vintage Inspired Apartment In Downtown Newberg, OR, holiday rental in Sherwood

A Handsome Newly Remodeled Vintage Inspired Apartment In Downtown Newberg, OR

2 bedrooms
2 bathrooms
Sleeps 4
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Top Rated Willamette River Farmhouse, holiday rental in Sherwood

Top Rated Willamette River Farmhouse

5 bedrooms
2 bathrooms
Sleeps 10
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Chehalem Crest - Wine Country Retreat. Mt. Hood View and on site vineyard!, holiday rental in Sherwood

Chehalem Crest - Wine Country Retreat. Mt. Hood View and on site vineyard!

5 bedrooms
4 bathrooms
Sleeps 12
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This Lake Oswego Cottage has stunning views of the Tualatin River!!, holiday rental in Sherwood

This Lake Oswego Cottage has stunning views of the Tualatin River!!

2 bedrooms
1 bathroom
Sleeps 4
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LAKESIDE URBAN INN . . . truly a HIDDEN GEM on the LAKE in Downtown Tualatin!!!, holiday rental in Sherwood

LAKESIDE URBAN INN . . . truly a HIDDEN GEM on the LAKE in Downtown Tualatin!!!

1 bedroom
1 bathroom
Sleeps 4
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Amani Acres-located in the heart of wine country-2 bedroom sleeps 6 1100 sq ft., holiday rental in Sherwood

Amani Acres-located in the heart of wine country-2 bedroom sleeps 6 1100 sq ft.

2 bedrooms
1 bathroom
Sleeps 6
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Chehalem Mountain Hideaway, holiday rental in Sherwood

Chehalem Mountain Hideaway

2 bedrooms
1 bathroom
Sleeps 4
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La Casa with Luxury Amenities, holiday rental in Sherwood

La Casa with Luxury Amenities

3 bedrooms
2 bathrooms
Sleeps 8
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Spacious Suite on Oregon Equestrian Estate, holiday rental in Sherwood

Spacious Suite on Oregon Equestrian Estate

3 bedrooms
2 bathrooms
Sleeps 10
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TRULY A TREASURE~MCA 524~Spectacular home with amazing outdoor living space., holiday rental in Sherwood

TRULY A TREASURE~MCA 524~Spectacular home with amazing outdoor living space.

3 bedrooms
2 bathrooms
Sleeps 8
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Victorian Secrets 1897 Home - Curious? Eclectic, convenient & ❤️ of wine country, holiday rental in Sherwood

Victorian Secrets 1897 Home - Curious? Eclectic, convenient & ❤️ of wine country

4 bedrooms
2 bathrooms
Sleeps 8
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The Suite will give you the comfort of home with detailed warm touches., holiday rental in Sherwood

The Suite will give you the comfort of home with detailed warm touches.

1 bedroom
1 bathroom
Sleeps 2
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Comfy & Bright 2BR Flat W/ Fenced Yard Near Washington Square, holiday rental in Sherwood

Comfy & Bright 2BR Flat W/ Fenced Yard Near Washington Square

2 bedrooms
1 bathroom
Sleeps 4
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THE TRAVELERS RETREAT at the COTTAGE- PORTLAND, holiday rental in Sherwood

THE TRAVELERS RETREAT at the COTTAGE- PORTLAND

1 bedroom
1 bathroom
Sleeps 2
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Luxurious Wine Country Estate with Mountain and Pastoral Views, holiday rental in Sherwood

Luxurious Wine Country Estate with Mountain and Pastoral Views

5 bedrooms
5 bathrooms
Sleeps 14
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A Tiny House on a lavender farm In Oregon's Wine Country, holiday rental in Sherwood

A Tiny House on a lavender farm In Oregon's Wine Country

1 bedroom
1 bathroom
Sleeps 2
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Bright*Private*Stylish 2BR Flat W/ Fenced Yard Near Washington Square, holiday rental in Sherwood

Bright*Private*Stylish 2BR Flat W/ Fenced Yard Near Washington Square

2 bedrooms
1 bathroom
Sleeps 4
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FAMILY-FRIENDLY Home in Newberg!!!, holiday rental in Sherwood

FAMILY-FRIENDLY Home in Newberg!!!

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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*Quiet 2BR | Home Away From Home | Nike + Intel Nearby *, holiday rental in Sherwood

*Quiet 2BR | Home Away From Home | Nike + Intel Nearby *

2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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ORIGINAL 1927 COZY LAKEFRONT BUNGALOW WITH WRAP AROUND PORCH, holiday rental in Sherwood

ORIGINAL 1927 COZY LAKEFRONT BUNGALOW WITH WRAP AROUND PORCH

3 bedrooms
2 bathrooms
Sleeps 6
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Attractive & Comfortable Upscale Condo Close to Everything, holiday rental in Sherwood

Attractive & Comfortable Upscale Condo Close to Everything

2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Estate surrounded by Vineyards & Horses, holiday rental in Sherwood

Beautiful Estate surrounded by Vineyards & Horses

6 bedrooms
5 bathrooms
Sleeps 15
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2Bd/1Ba Family-Friendly Executive Rental in Tigard, holiday rental in Sherwood

2Bd/1Ba Family-Friendly Executive Rental in Tigard

2 bedrooms
1 bathroom
Sleeps 5
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Great for extended stays near Nike and Intel, holiday rental in Sherwood

Great for extended stays near Nike and Intel

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Feathered Nest situated on two private acres in the Heart of Oregon Wine Country, holiday rental in Sherwood

Feathered Nest situated on two private acres in the Heart of Oregon Wine Country

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Wine Country boho-chic bungalow, 2 master suites, walk to restaurants & wineries, holiday rental in Sherwood

Wine Country boho-chic bungalow, 2 master suites, walk to restaurants & wineries

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Wine country beauty that is family friendly!, holiday rental in Sherwood

Wine country beauty that is family friendly!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Valley Wine Cottage - A Luxury Vacation Rental in the Willamette Valley, holiday rental in Sherwood

The Valley Wine Cottage - A Luxury Vacation Rental in the Willamette Valley

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Home Away from Home Studio, holiday rental in Sherwood

Home Away from Home Studio

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Wine Country Vineyard and Mountain Views, holiday rental in Sherwood

Wine Country Vineyard and Mountain Views

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Willamette Valley Apt - Surrounded by Wineries!, holiday rental in Sherwood

Willamette Valley Apt - Surrounded by Wineries!

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Modern Townhome With Open Floor Plan and Pool Table Near Washington Square, 8.5, holiday rental in Sherwood

Modern Townhome With Open Floor Plan and Pool Table Near Washington Square, 8.5

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Wine Country Bungalow With Patio Overlooking Newly Planted Vineyard an, holiday rental in Sherwood

Renovated Wine Country Bungalow With Patio Overlooking Newly Planted Vineyard an

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Pearl: Luxury Pet-Friendly Historic Home in Downtown Newberg, holiday rental in Sherwood

The Pearl: Luxury Pet-Friendly Historic Home in Downtown Newberg

4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Modern Open Floor Plan In SW Portland With Hot Tub, Basketball Court, Huge Patio, holiday rental in Sherwood

Modern Open Floor Plan In SW Portland With Hot Tub, Basketball Court, Huge Patio

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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SW Portland Single Level Open Floor Plan With Wooded Patio, 20 Min to Downtown,, holiday rental in Sherwood

SW Portland Single Level Open Floor Plan With Wooded Patio, 20 Min to Downtown,

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Southwest Portland Single Level Wheelchair Accessible Home With Open Floor Plan, holiday rental in Sherwood

Southwest Portland Single Level Wheelchair Accessible Home With Open Floor Plan

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Newly Renovated Bungalow With Patio and Fireplace w/ Vineyard & Mtn Views, Minut, holiday rental in Sherwood

Newly Renovated Bungalow With Patio and Fireplace w/ Vineyard & Mtn Views, Minut

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Incredible Wine Country Home! Close to Breweries & Dining, Hot Tub, Gas Grill, G, holiday rental in Sherwood

Incredible Wine Country Home! Close to Breweries & Dining, Hot Tub, Gas Grill, G

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Tigard Retreat w/Deck, 15 Mins From Portland!, holiday rental in Sherwood

NEW! Tigard Retreat w/Deck, 15 Mins From Portland!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Craftsman, Five Master Suites, Two Patios, BBQ, Free Wine Tastings, Walk, holiday rental in Sherwood

Elegant Craftsman, Five Master Suites, Two Patios, BBQ, Free Wine Tastings, Walk

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Comfy and Quiet Retreat, Next to Parks and Trails, Single Level Design, BBQ, 11, holiday rental in Sherwood

Comfy and Quiet Retreat, Next to Parks and Trails, Single Level Design, BBQ, 11

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Phenomenal Single Level Home Featuring Incredible Outdoor Golf Option w/ Gazebo,, holiday rental in Sherwood

Phenomenal Single Level Home Featuring Incredible Outdoor Golf Option w/ Gazebo,

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Carman Garden Bungalow, holiday rental in Sherwood

Carman Garden Bungalow

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Roosters Coop Lodge-Style Retreat, holiday rental in Sherwood

Roosters Coop Lodge-Style Retreat

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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