48+ Vacation Rentals Near Woodstock

NearbyHoliday - Vacation Rentals in Woodstock

a kitchen with white cabinets and a living room at Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars in Portland

From US $235

Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars

9.2 (16 Reviews) Apartment

The entire place is yours • 93 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 4.5km to center

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a living room with an orange couch and two windows at Stay Portland - Bright Studio Apartment - Food Carts & Local Shops in Portland

From US $139

Stay Portland - Bright Studio Apartment - Food Carts & Local Shops

8.9 (16 Reviews) Apartment

The entire place is yours • 31 m² size • Free parking

Portland Buckman • In Woodstock · 4.4km to center

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a living room with a couch and a window at Stay Portland - Perfect Portland Micro By Top Shopping & Dinning in Portland

From US $124

Stay Portland - Perfect Portland Micro By Top Shopping & Dinning

9.2 (14 Reviews) Holiday_home

The entire place is yours • 26 m² size • Free parking

Portland Buckman • In Woodstock · 4.2km to center

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a living room with a couch and a tv at Stay Portland - Moab Vibes in PDX- Walk to Local Coffee & Food in Portland

From US $199

Stay Portland - Moab Vibes in PDX- Walk to Local Coffee & Food

8.3 (15 Reviews) Holiday_home

The entire place is yours • 65 m² size • Free parking

Portland Buckman • In Woodstock · 4.2km to center

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a living room with a couch and a kitchen at Stay Portland - The Sunnyside Cottage, Local Shops & Nightlife in Portland

From US $223

Stay Portland - The Sunnyside Cottage, Local Shops & Nightlife

9.8 (5 Reviews) Apartment

The entire place is yours • 70 m² size • Free parking

Portland Sunnyside • In Woodstock · 4.4km to center

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a living room with a blue couch and a table at Stay Portland - Retro Modern 2-Bedroom with 90 WalkScore in Portland

From US $191

Stay Portland - Retro Modern 2-Bedroom with 90 WalkScore

9.1 (10 Reviews) Apartment

The entire place is yours • 73 m² size • Free parking

Portland Buckman • In Woodstock · 4.4km to center

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a living room with a green couch and a flat screen tv at Stay Portland - The Woodstock Inn - Reed College & Vintage Shops in Portland

From US $141

Stay Portland - The Woodstock Inn - Reed College & Vintage Shops

8.8 (11 Reviews) Apartment

The entire place is yours • Free parking • Free WiFi

Portland Woodstock • In Woodstock · 1.2km to center

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a kitchen with a sink and a bed in a room at Stay Portland - Tiny Aztec - Walk to Local Shops & Restaurants in Portland

From US $137

Stay Portland - Tiny Aztec - Walk to Local Shops & Restaurants

10.0 (7 Reviews) Holiday_home

The entire place is yours • 19 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 3.0km to center

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Luxury Places to Stay in Woodstock

Over 11+ Luxury Places to Stay in or Near Woodstock

a white building with a tree in front of it at River's Edge Hotel Portland, Tapestry Collection by Hilton in Portland

From US $122

River's Edge Hotel Portland, Tapestry Collection by Hilton

8.5 (283 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Portland South Portland • In Woodstock · 4.7km to center

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a kitchen and living room with a green wall at Private Oasis! Cozy & Close to Everything! in Portland

From US $208

Private Oasis! Cozy & Close to Everything!

10.0 (3 Reviews) Guest_house

Kitchen • Washing machine • Free WiFi

Portland Richmond • In Woodstock · 3.1km to center

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a living room with a bed and a couch at Boutique Style Apartment in the heart of SE in Portland

From US $158

Boutique Style Apartment in the heart of SE

9.2 (21 Reviews) Apartment

The entire place is yours • 56 m² size • Free parking

Portland Sunnyside • In Woodstock · 4.5km to center

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a walkway leading to a white house with flowers at The Secret Garden in Portland

From US $133

The Secret Garden

9.7 (47 Reviews) Apartment

The entire place is yours • 37 m² size • Free on-site parking

Portland Mount Tabor • In Woodstock · 3.9km to center

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a kitchen with white cabinets and a living room at Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars in Portland

From US $235

Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars

9.2 (16 Reviews) Apartment

The entire place is yours • 93 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 4.5km to center

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a house with trees in front of it at Southeast Portland Comfy & Eclectic Craftsman Home in Portland

From US $375

Southeast Portland Comfy & Eclectic Craftsman Home

9.6 (13 Reviews) Holiday_home

The entire place is yours • 167 m² size • Kitchen

Portland Hosford Abernethy • In Woodstock · 3.1km to center

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a bedroom with a bed with a blue wall at The Hawthorne Hideaway in Portland

From US $283

The Hawthorne Hideaway

9.5 (19 Reviews) Holiday_home

The entire place is yours • 46 m² size • Kitchen

Portland Sunnyside • In Woodstock · 3.7km to center

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a living room with couches and a painting on the wall at The Flying Whale-MountTabor. in Portland

From US $323

The Flying Whale-MountTabor.

9.6 (7 Reviews) Apartment

The entire place is yours • 137 m² size • Free on-site parking

Portland Mount Tabor • In Woodstock · 4.9km to center

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Pet-Friendly Vacation Rentals in Woodstock

Over 31+ Pet-Friendly Vacation Rentals in or Near Woodstock

a white building with a tree in front of it at River's Edge Hotel Portland, Tapestry Collection by Hilton in Portland

From US $122

River's Edge Hotel Portland, Tapestry Collection by Hilton Pets allowed

8.5 (283 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Portland South Portland • In Woodstock · 4.7km to center

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a kitchen with white cabinets and a living room at Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars in Portland

From US $235

Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars Pets allowed

9.2 (16 Reviews) Apartment

The entire place is yours • 93 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 4.5km to center

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a living room with an orange couch and two windows at Stay Portland - Bright Studio Apartment - Food Carts & Local Shops in Portland

From US $139

Stay Portland - Bright Studio Apartment - Food Carts & Local Shops Pets allowed

8.9 (16 Reviews) Apartment

The entire place is yours • 31 m² size • Free parking

Portland Buckman • In Woodstock · 4.4km to center

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a living room with a couch and a window at Stay Portland - Perfect Portland Micro By Top Shopping & Dinning in Portland

From US $124

Stay Portland - Perfect Portland Micro By Top Shopping & Dinning Pets allowed

9.2 (14 Reviews) Holiday_home

The entire place is yours • 26 m² size • Free parking

Portland Buckman • In Woodstock · 4.2km to center

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a living room with a blue couch and a table at Stay Portland - Retro Modern 2-Bedroom with 90 WalkScore in Portland

From US $191

Stay Portland - Retro Modern 2-Bedroom with 90 WalkScore Pets allowed

9.1 (10 Reviews) Apartment

The entire place is yours • 73 m² size • Free parking

Portland Buckman • In Woodstock · 4.4km to center

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a living room with a couch and a tv at Stay Portland - Moab Vibes in PDX- Walk to Local Coffee & Food in Portland

From US $199

Stay Portland - Moab Vibes in PDX- Walk to Local Coffee & Food Pets allowed

8.3 (15 Reviews) Holiday_home

The entire place is yours • 65 m² size • Free parking

Portland Buckman • In Woodstock · 4.2km to center

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a kitchen with a sink and a bed in a room at Stay Portland - Tiny Aztec - Walk to Local Shops & Restaurants in Portland

From US $137

Stay Portland - Tiny Aztec - Walk to Local Shops & Restaurants Pets allowed

10.0 (7 Reviews) Holiday_home

The entire place is yours • 19 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 3.0km to center

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a living room with a couch and a kitchen at Stay Portland - The Sunnyside Cottage, Local Shops & Nightlife in Portland

From US $223

Stay Portland - The Sunnyside Cottage, Local Shops & Nightlife Pets allowed

9.8 (5 Reviews) Apartment

The entire place is yours • 70 m² size • Free parking

Portland Sunnyside • In Woodstock · 4.4km to center

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Vacation Rentals in Woodstock

Over 35+ Vacation Rentals in or Near Woodstock

a kitchen with white cabinets and a living room at Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars in Portland

From US $235

Stay Portland - Perfect Portland Farmhouse Loft - Breweries & Bars

9.2 (16 Reviews) Apartment

The entire place is yours • 93 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 4.5km to center

Best Price Match

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a living room with an orange couch and two windows at Stay Portland - Bright Studio Apartment - Food Carts & Local Shops in Portland

From US $139

Stay Portland - Bright Studio Apartment - Food Carts & Local Shops

8.9 (16 Reviews) Apartment

The entire place is yours • 31 m² size • Free parking

Portland Buckman • In Woodstock · 4.4km to center

Best Price Match

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a living room with a couch and a window at Stay Portland - Perfect Portland Micro By Top Shopping & Dinning in Portland

From US $124

Stay Portland - Perfect Portland Micro By Top Shopping & Dinning

9.2 (14 Reviews) Holiday_home

The entire place is yours • 26 m² size • Free parking

Portland Buckman • In Woodstock · 4.2km to center

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a living room with a couch and a tv at Stay Portland - Moab Vibes in PDX- Walk to Local Coffee & Food in Portland

From US $199

Stay Portland - Moab Vibes in PDX- Walk to Local Coffee & Food

8.3 (15 Reviews) Holiday_home

The entire place is yours • 65 m² size • Free parking

Portland Buckman • In Woodstock · 4.2km to center

Best Price Match

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a living room with a couch and a kitchen at Stay Portland - The Sunnyside Cottage, Local Shops & Nightlife in Portland

From US $223

Stay Portland - The Sunnyside Cottage, Local Shops & Nightlife

9.8 (5 Reviews) Apartment

The entire place is yours • 70 m² size • Free parking

Portland Sunnyside • In Woodstock · 4.4km to center

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a living room with a blue couch and a table at Stay Portland - Retro Modern 2-Bedroom with 90 WalkScore in Portland

From US $191

Stay Portland - Retro Modern 2-Bedroom with 90 WalkScore

9.1 (10 Reviews) Apartment

The entire place is yours • 73 m² size • Free parking

Portland Buckman • In Woodstock · 4.4km to center

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a living room with a green couch and a flat screen tv at Stay Portland - The Woodstock Inn - Reed College & Vintage Shops in Portland

From US $141

Stay Portland - The Woodstock Inn - Reed College & Vintage Shops

8.8 (11 Reviews) Apartment

The entire place is yours • Free parking • Free WiFi

Portland Woodstock • In Woodstock · 1.2km to center

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a kitchen with a sink and a bed in a room at Stay Portland - Tiny Aztec - Walk to Local Shops & Restaurants in Portland

From US $137

Stay Portland - Tiny Aztec - Walk to Local Shops & Restaurants

10.0 (7 Reviews) Holiday_home

The entire place is yours • 19 m² size • Free parking

Portland Hosford Abernethy • In Woodstock · 3.0km to center

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Hotels in Woodstock

Over 13+ Hotels in or Near Woodstock

a white building with a tree in front of it at River's Edge Hotel Portland, Tapestry Collection by Hilton in Portland

From US $122

River's Edge Hotel Portland, Tapestry Collection by Hilton

8.5 (283 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Portland South Portland • In Woodstock · 4.7km to center

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a building with a welcome sign in front of it at Motel 6-Portland, OR - Central in Portland

From US $60

Motel 6-Portland, OR - Central

6.0 (541 Reviews) Hotel

Free on-site parking • Outdoor swimming pool • Pet friendly

Portland Creston Kenilworth • In Woodstock · 2.4km to center

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a green house with a white porch and windows at Bluebird Guesthouse in Portland

From US $131

Bluebird Guesthouse

9.3 (150 Reviews) Inn

Breakfast • Free parking • Free WiFi

Portland Richmond • In Woodstock · 3.0km to center

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a front porch of a white house with a wooden door at Evermore Guesthouse in Portland

From US $172

Evermore Guesthouse

9.3 (86 Reviews) Guest_house

Breakfast • Free on-site parking • Balcony

Portland Richmond • In Woodstock · 2.7km to center

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a living room with a couch and a table at Hidden Zen in Portland

From US $149

8.8 (28 Reviews) Hotel

Private bathroom • BBQ facilities • Bathtub

Portland Eastmoreland • In Woodstock · 1.7km to center

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a store front of a building with a window at Unicorn Inn by OYO Portland in Portland

From US $100

Unicorn Inn by OYO Portland

6.4 (41 Reviews) Hotel

Free on-site parking • Pet friendly • Free WiFi

Portland Powellhurst Gilbert • In Woodstock · 3.6km to center

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a hotel with a gas station in front of it at Motel 6 Portland OR Southeast in Portland

From US $79

Motel 6 Portland OR Southeast

6.4 (123 Reviews) Hotel

Free on-site parking • Pet friendly • Free WiFi

Portland Lents • In Woodstock · 3.0km to center

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a bedroom with a bed and a couch and a table at Rosie’s Retro River Flat in Portland

From US $124

Rosie’s Retro River Flat

8.8 (9 Reviews) Hotel

Private bathroom • Facilities for disabled guests • Kitchen

Portland South Portland • In Woodstock · 4.7km to center

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Cheap Places to Stay in Woodstock

Over 13+ Cheap Places to Stay in or Near Woodstock

a building with a welcome sign in front of it at Motel 6-Portland, OR - Central in Portland

From US $60

Motel 6-Portland, OR - Central

6.0 (541 Reviews) Hotel

Free on-site parking • Outdoor swimming pool • Pet friendly

Portland Creston Kenilworth • In Woodstock · 2.4km to center

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a hotel room with a bed and a desk at Del Rancho Motel in Portland

From US $70

Del Rancho Motel

9.7 (3 Reviews) Hotel

Free on-site parking • Free WiFi • Private bathroom

Portland Lents • In Woodstock · 3.1km to center

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a building with red doors and windows on a street at Aaron Motel in Portland

From US $70

5.8 (5 Reviews) Motel

Free on-site parking • Hot tub • Free WiFi

Portland Powellhurst Gilbert • In Woodstock · 3.8km to center

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a hotel with a gas station in front of it at Motel 6 Portland OR Southeast in Portland

From US $79

Motel 6 Portland OR Southeast

6.4 (123 Reviews) Hotel

Free on-site parking • Pet friendly • Free WiFi

Portland Lents • In Woodstock · 3.0km to center

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a hotel room with a bed and a flat screen tv at Del Rancho Motel By Townhouse Portland OR Hwy 205 in Portland

From US $83

Del Rancho Motel By Townhouse Portland OR Hwy 205

4.1 (41 Reviews) Motel

Free on-site parking • Pets allowed • Free WiFi

Portland Lents • In Woodstock · 3.0km to center

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a store front of a building with a window at Unicorn Inn by OYO Portland in Portland

From US $100

Unicorn Inn by OYO Portland

6.4 (41 Reviews) Hotel

Free on-site parking • Pet friendly • Free WiFi

Portland Powellhurst Gilbert • In Woodstock · 3.6km to center

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a motel sign in front of a building at Best Value Inn by OYO Portland OR South East in Portland

From US $116

Best Value Inn by OYO Portland OR South East

3.5 (12 Reviews) Motel

Free on-site parking • Wifi in all areas • Private bathroom

Portland Powellhurst Gilbert • In Woodstock · 3.5km to center

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a white building with a tree in front of it at River's Edge Hotel Portland, Tapestry Collection by Hilton in Portland

From US $122

River's Edge Hotel Portland, Tapestry Collection by Hilton

8.5 (283 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Portland South Portland • In Woodstock · 4.7km to center

Best Price Match

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Hotels with Suites in Woodstock

Over 2+ Hotels with Suites in or Near Woodstock

a white building with a tree in front of it at River's Edge Hotel Portland, Tapestry Collection by Hilton in Portland

From US $122

River's Edge Hotel Portland, Tapestry Collection by Hilton

8.5 (283 Reviews) Hotel

Private parking • Restaurant • Pet friendly

Portland South Portland • In Woodstock · 4.7km to center

Best Price Match

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a front porch of a white house with a wooden door at Evermore Guesthouse in Portland

From US $172

Evermore Guesthouse

9.3 (86 Reviews) Guest_house

Breakfast • Free on-site parking • Balcony

Portland Richmond • In Woodstock · 2.7km to center

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About Woodstock Vacation Rentals

Looking for places to stay in Woodstock? Compare top options in Portland.

With more than 48 Woodstock vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Woodstock.

Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Woodstock. Prices average US $147 a night.

NearbyHoliday makes it easy and safe to find and compare vacation rentals in Woodstock, with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Stay Categories in Woodstock

Category	Count
Vacation Rentals	35
Pet-Friendly	31
Cheap Rentals	13
Hotels	13
Luxury Rentals	11
Hotels with Suites	2

Use These Quick Filters to Find a Vacation Rental in Woodstock

Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Woodstock.

Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Woodstock. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.

Weather in Woodstock

Average temperatures and rainfall by month range to help plan your stay in Woodstock.

Mar - May

Avg High16°C / 60°F

Avg Low6°C / 42°F

Rainfall114 mm / 4.5 in

Jun - Aug

Avg High27°C / 81°F

Avg Low13°C / 56°F

Rainfall26 mm / 1 in

Sep - Nov

Avg High18°C / 64°F

Avg Low8°C / 46°F

Rainfall128 mm / 5 in

Dec - Feb

Avg High9°C / 48°F

Avg Low2°C / 36°F

Rainfall190 mm / 7.5 in

Other Places to Stay Near Woodstock

Woodstock Vacation Rental Frequently Asked Questions

There are a lot of options in Woodstock. If you plan on staying in the Woodstock area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Woodstock: