Fall brings browns, reds, yellows and gold to Portland, Oregon.
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B&Bs and Inns in Oregon with Outdoor Pools

Browse romantic b&bs and inns in oregon for couples with outdoor pools, shaped for weekend trips, special occasions, and more comfortable getaways across Oregon.

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Matching Your Search

B&Bs and Inns in Oregon with Outdoor Pools

Browse romantic b&bs and inns in oregon for couples with outdoor pools, shaped for weekend trips, special occasions, and more comfortable getaways across Oregon.

Cousins' Country Inn
Photo of Cousins' Country Inn
Photo of Cousins' Country Inn
Photo of Cousins' Country Inn
Photo of Cousins' Country Inn
Cousins' Country Inn
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Photo of Cousins' Country Inn
Photo of Cousins' Country Inn
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Countryside Retreat
★4.4

Cousins' Country Inn

From
$99
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Cousins' Country Inn in The Dalles, Oregon, is a perfect countryside retreat for couples. Enjoy homestyle meals, cozy rooms with fireplaces, a seasonal heated pool, and romantic outdoor jacuzzis while exploring the stunning Columbia River Gorge.

Hot TubFireplaceDining
Riverside Inn
Anniversary Choice

Riverside Inn

Guest Rating
4.3★
From$115
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Curated Highlights
01Balcony / Patio
02Breakfast
03Outdoor Pool
Cimarron Inn Klamath Falls
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Photo of Cimarron Inn Klamath Falls
Photo of Cimarron Inn Klamath Falls
Photo of Cimarron Inn Klamath Falls
Cimarron Inn Klamath Falls
Photo of Cimarron Inn Klamath Falls
Photo of Cimarron Inn Klamath Falls
Photo of Cimarron Inn Klamath Falls
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Countryside Retreat
★3.9

Cimarron Inn Klamath Falls

From
$77
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Cimarron Inn Klamath Falls is a cozy hotel offering affordable stays that are perfect for couples. Located near Crater Lake, this pet-friendly hotel provides comfy rooms, complimentary breakfast, and a seasonal outdoor pool, ideal for romantic retreat seekers who love nature and convenience.

BreakfastOutdoor PoolPet Friendly
Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
Photo of Riverfront Inn - Roseburg
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Countryside Retreat
★4.1

Riverfront Inn - Roseburg

From
$104
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The Riverfront Inn - Roseburg offers scenic views of the Umpqua River, cozy remodeled rooms, and nearby wineries, making it an ideal retreat for adventurous couples seeking romance and relaxation in Oregon’s stunning countryside.

Balcony / PatioBreakfastOutdoor Pool
R & R Guesthouse
Anniversary Choice

R & R Guesthouse

Guest Rating
4.9★
From$495
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Curated Highlights
01Private Hot Tub
02Hot Tub
03Soaking Tub
Ashland Carter House
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Photo of Ashland Carter House
Photo of Ashland Carter House
Photo of Ashland Carter House
Ashland Carter House
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Photo of Ashland Carter House
Photo of Ashland Carter House
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Countryside Retreat
★4.6

Ashland Carter House

From
$189
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Ashland Carter House, a historic gem in Downtown Ashland, Oregon, offers charming nightly rentals with easy access to theaters, dining, and local activities. Ideal for romantic getaways and exploring Southern Oregon's treasures.

Outdoor PoolParkingFree WiFi
Destination Pulse

Where Couples Stay in Oregon

Explore 63 curated cities across Oregon, from well-known romantic hubs to quieter places worth building a weekend around.

Cities Represented by These Stays

These 5 cities have hotels matching your current search.

5 Cities
Columbia Gorge river view from The Dalles, OR, USA
2 Matches

The Dalles

Experience the charm of The Dalles with cozy stays, scenic Columbia River views, and nearby wineries perfect for a romantic retreat.

Matching City
Ashland, OREGON, USA
1 Match

Ashland

Experience romance and culture in this charming theater town nestled in the Rogue Valley.

Matching City
Rafting through the notorious rapid, Blossom Bar, on the Wild & Scenic Section of the Rogue River.
1 Match

Grants Pass

Discover inviting accommodations in Grants Pass, offering peaceful riverfront settings, charming downtown vibes, and endless opportunities for romance and relaxation.

Matching City
Klamath Falls, OR, USA
1 Match

Klamath Falls

Escape to the natural beauty of Klamath Falls, where cozy lakeside stays, breathtaking mountain views, and outdoor adventures create the perfect romantic retreat.

Matching City
Autumn in Roseburg, Oregon, US
1 Match

Roseburg

Escape to the heart of Oregon’s Umpqua Valley, Roseburg, where cozy stays, scenic wineries, and breathtaking waterfalls create the perfect romantic retreat.

Matching City

Browse Every City

Portland, Oregon, USA

Portland

38 Stays

Deschutes River, Bend, OREGON, United States

Bend

30 Stays

Ashland, OREGON, USA

Ashland

25 Stays · 1 Match

An empty campus in Eugene, OR, USA

Eugene

23 Stays

Winter in Medford, Oregon, USA

Medford

23 Stays

Cannon Beach, Cannon Beach, Oregon, United States

Cannon Beach

22 Stays

Beach at Seaside, Oregon, USA

Seaside

21 Stays

A beautiful day in Lincoln City, Oregon.

Lincoln City

20 Stays

A lighthouse beneath a starry sky in Newport, Oregon.

Newport

19 Stays

Rafting through the notorious rapid, Blossom Bar, on the Wild & Scenic Section of the Rogue River.

Grants Pass

17 Stays · 1 Match

Orenco Station, Hillsboro, OR 97124, USA

Hillsboro

17 Stays

Klamath Falls, OR, USA

Klamath Falls

16 Stays · 1 Match

Astoria-Megler Bridge, Astoria, OREGON 97103, USA

Astoria

14 Stays

The 22-foot-tall statue of "the gold pioneer" that sits on top of the State of Oregon's capitol building.

Salem

14 Stays

Siuslaw River Bridge in Florence, Oregon, USA

Florence

12 Stays

Pendleton Woolen Mills Clothing Store

Pendleton

12 Stays

Hood River County, Oregon, USA

Hood River

11 Stays

Redmond, Oregon, USA

Redmond

10 Stays

Columbia Gorge river view from The Dalles, OR, USA

The Dalles

10 Stays · 2 Matches

Nike World Headquarters, One Bowerman Drive, Beaverton, OR, USA

Beaverton

9 Stays

Oregon State University, Corvallis, OR, USA

Corvallis

9 Stays

Autumn in the Pacific Northwest, Eugene/Springfield, Oregon, USA

Springfield

9 Stays

Red barn on a Willamette Valley hilltop in Albany, Oregon, USA

Albany

8 Stays

Harris Beach State Park, Brookings, OREGON, USA

Brookings

8 Stays

Autumn in Roseburg, Oregon, US

Roseburg

8 Stays · 1 Match

Sunset at Coquille River Lighthouse, Bullards Beach Road, Bandon, OR, USA

Bandon

7 Stays

Sunset behind a campground with a small road and a picnic table between trees near Clackamas River, Clackamas, Oregon, USA

Clackamas

7 Stays

A beautifully eroded bit of coastline outside of Depoe Bay, Oregon.

Depoe Bay

7 Stays

Lake Oswego, United States

Lake Oswego

7 Stays

Pioneer Hall at Linfield University, McMinnville, United States

McMinnville

7 Stays

Sisters, OR, USA

Sisters

7 Stays

Nature's path - Coos Bay, OR, USA

Coos Bay

6 Stays

Rugged natural beauty of the Gold Beach, Oregon Coast.

Gold Beach

6 Stays

Downtown Jacksonville, OR, USA

Jacksonville

6 Stays

Cape Kiwanda, Pacific City, OR, USA

Pacific City

6 Stays

Portland Oregon Temple near Tigard

Tigard

6 Stays

Yachats, Oregon, United States

Yachats

6 Stays

Mount Jefferson, Oregon, USA

Madras

5 Stays

Two chairs and a bottle of wine in front of a vineyard in Newberg, OR, USA

Newberg

5 Stays

Blue Saturday morning walk as a spring storm approaches Gearhart on the Oregon Coast.

Gearhart

4 Stays

Coos Bay, OR, USA

North Bend

4 Stays

Warm tall grass with a line of trees backed by the morning fog in Troutdale, OR, USA

Troutdale

4 Stays

Trillium Lake’s serenity welcomes Mt. Hood near Government Camp

Welches

4 Stays

Oregon Coast Meets Beach at Oswald West State Park, Arch Cape, OR, USA

Arch Cape

3 Stays

Jackson County Expo - Central Point, Oregon, USA

Central Point

3 Stays

Currin Covered Bridge

Cottage Grove

3 Stays

Grapes growing on a vineyard in Dundee, Oregon.

Dundee

3 Stays

An image of the Garibaldi’s harbor

Garibaldi

3 Stays

Mt. Hood Park Division Recreation Area, Government Camp, Oregon, USA

Government Camp

3 Stays

Nighttime wet street in Gresham, OR, USA

Gresham

3 Stays

Manzanita, Oregon, United States

Manzanita

3 Stays

A sunset view from a house in Prineville, Oregon.

Prineville

3 Stays

Aerial view of Rockaway Beach, Oregon, USA

Rockaway Beach

3 Stays

Willamette Valley vineyards on a misty morning near Carlton, Oregon

Carlton

2 Stays

Crater Lake, Chiloquin, United States

Chiloquin

2 Stays

Crater Lake National Park, (Fort Klamath) United States

Fort Klamath

2 Stays

Vineyards in Willamette Valley, Lebanon, Oregon, USA

Lebanon

2 Stays

A strip of land between the Pacific Ocean and Tillamook Bay near Bay City in Oregon.

Bay City

1 Stay

McPhillips Beach, McPhillips Drive, Cloverdale, OR, USA

Cloverdale

1 Stay

Crooked River Ranch, OR, USA

Crooked River Ranch

1 Stay

View of the cove at Harris Beach State Park from the highway looking over the Pacific ocean near Brookings and Harbor, Oregon

Harbor

1 Stay

Route 97 highway that goes past Smith Rock State Park near Terrebonne, OR, USA

Terrebonne

1 Stay

Winchester Bay, OR, USA

Winchester Bay

1 Stay

Regional Collections

Choose Your Romantic Style in Oregon

Browse the getaway styles that shape our Oregon collection, from spa weekends and city stays to scenic retreats made for slower, more memorable trips together.

Neatly arranged vineyards cover a hill outside of Salem, Oregon.
Signature Style in Oregon

Countryside Retreats

Explore countryside b&bs and inns in Oregon with outdoor pools.

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View of the rock in the ocean - Cannon beach, Oregon, United states.

Beachfront Retreats

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The Portland, OR Skyline at sunset. - City skyline during night time.

Urban Escapes

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Multnomah Falls, Oregon, USA

Mountain Getaways

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A person sitting on brown wooden rocking chair near Crater Lake, Oregon, USA

Lakefront Retreats

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Double Bed in Cozy Hotel Room

Best Value Escapes

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Modern Luxury Style Hotel Room

Luxury Retreats

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Tray with candles, flowers, and bath salts on a hot tub

Wellness and Spa Getaways

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