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Gladstone Holiday Rentals

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50 rentals in Gladstone.
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South Of Portland Restored Victorian, Two Blocks To Park and Clackamas River, 11, holiday rental in Gladstone

South Of Portland Restored Victorian, Two Blocks To Park and Clackamas River, 11

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Top Rated Willamette River Farmhouse, holiday rental in Gladstone

Top Rated Willamette River Farmhouse

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Brand New Guesthouse with Riverfront Patio, holiday rental in Gladstone

Brand New Guesthouse with Riverfront Patio

2 bedrooms
1 bathroom
Sleeps 8
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LAKESIDE URBAN INN . . . truly a HIDDEN GEM on the LAKE in Downtown Tualatin!!!, holiday rental in Gladstone

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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This Lake Oswego Cottage has stunning views of the Tualatin River!!, holiday rental in Gladstone

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Willamette Riverfront Oasis - Whole House, holiday rental in Gladstone

Private Willamette Riverfront Oasis - Whole House

5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Live the Dream on the Lovely Willamette River, holiday rental in Gladstone

Live the Dream on the Lovely Willamette River

Downtown
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Willamette riverfront  with stunning view near downtown Milwaukie and Sellwood, holiday rental in Gladstone

Willamette riverfront with stunning view near downtown Milwaukie and Sellwood

3 bedrooms
2 bathrooms
Sleeps 8
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La Casa with Luxury Amenities, holiday rental in Gladstone

La Casa with Luxury Amenities

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Guest Cottage In First Addition Lake Oswego, holiday rental in Gladstone

Private Guest Cottage In First Addition Lake Oswego

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Suite will give you the comfort of home with detailed warm touches., holiday rental in Gladstone

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious Suite on Oregon Equestrian Estate, holiday rental in Gladstone

Spacious Suite on Oregon Equestrian Estate

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Private Willamette Riverfront Oasis - Main Level, holiday rental in Gladstone

Private Willamette Riverfront Oasis - Main Level

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Charming Peaceful Get-a-way, holiday rental in Gladstone

Charming Peaceful Get-a-way

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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THE TRAVELERS RETREAT at the COTTAGE- PORTLAND, holiday rental in Gladstone

THE TRAVELERS RETREAT at the COTTAGE- PORTLAND

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic English Country Lake House, holiday rental in Gladstone

Historic English Country Lake House

3 bedrooms
2 bathrooms
Sleeps 5
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Gem close to downtown!, holiday rental in Gladstone

Gem close to downtown!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Blessings Farm Hideaway, holiday rental in Gladstone

The Blessings Farm Hideaway

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Wescott House in Historic Willamette District, holiday rental in Gladstone

Wescott House in Historic Willamette District

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sunset Vista in Happy Valley, holiday rental in Gladstone

Sunset Vista in Happy Valley

5 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Home in Spectacular Setting With Fabulous River Views!, holiday rental in Gladstone

Beautiful Home in Spectacular Setting With Fabulous River Views!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lovely Art Filled Home 15 Min to Downtown, holiday rental in Gladstone

Lovely Art Filled Home 15 Min to Downtown

2 bedrooms
1 bathroom
Sleeps 4
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ORIGINAL 1927 COZY LAKEFRONT BUNGALOW WITH WRAP AROUND PORCH, holiday rental in Gladstone

ORIGINAL 1927 COZY LAKEFRONT BUNGALOW WITH WRAP AROUND PORCH

3 bedrooms
2 bathrooms
Sleeps 6
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Guest House located in between Lake Oswego and West Linn.  20 Minutes, holiday rental in Gladstone

Guest House located in between Lake Oswego and West Linn. 20 Minutes

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Better than a 5-star hotel for extended business stay or romantic getaway, holiday rental in Gladstone

Better than a 5-star hotel for extended business stay or romantic getaway

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Attractive & Comfortable Upscale Condo Close to Everything, holiday rental in Gladstone

Attractive & Comfortable Upscale Condo Close to Everything

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private house on the Lake for Monthly rent, holiday rental in Gladstone

Private house on the Lake for Monthly rent

5 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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MODERN COUNTRY ESTATE, holiday rental in Gladstone

MODERN COUNTRY ESTATE

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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West Linn Oregon Relaxing Escape 20 Minutes to Downtown Portland, holiday rental in Gladstone

West Linn Oregon Relaxing Escape 20 Minutes to Downtown Portland

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant & Comfortable House by Willamette River!, holiday rental in Gladstone

Elegant & Comfortable House by Willamette River!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Close in SW Portland - 5 mins to Downtown/OHSU - 3 Bedroom House - Large Yard, holiday rental in Gladstone

Close in SW Portland - 5 mins to Downtown/OHSU - 3 Bedroom House - Large Yard

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious 3 Bedroom Townhouse in Happy Valley, holiday rental in Gladstone

Spacious 3 Bedroom Townhouse in Happy Valley

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated Retreat w/ Huge Gorgeous Deck on Green Space, Ping Pong Table, 1, holiday rental in Gladstone

Newly Renovated Retreat w/ Huge Gorgeous Deck on Green Space, Ping Pong Table, 1

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Perfect Couples Escape! Next to MAX Station ~ 7Miles 2 Downtown ~ Quiet Neighbor, holiday rental in Gladstone

Perfect Couples Escape! Next to MAX Station ~ 7Miles 2 Downtown ~ Quiet Neighbor

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Southeast Portland Construction, Bright Open Floor Plan, Foosball Table, Nex, holiday rental in Gladstone

New Southeast Portland Construction, Bright Open Floor Plan, Foosball Table, Nex

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Southeast Portland Construction, Bright Open Floor Plan, Foosball Table, Wal, holiday rental in Gladstone

New Southeast Portland Construction, Bright Open Floor Plan, Foosball Table, Wal

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Brand New Southeast Portland Studio, Bright Open Floor Plan, Next to MAX Station, holiday rental in Gladstone

Brand New Southeast Portland Studio, Bright Open Floor Plan, Next to MAX Station

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Incredible Home w/ Enormous Deck and View, Media Room, Foosball, Near Nature Par, holiday rental in Gladstone

Incredible Home w/ Enormous Deck and View, Media Room, Foosball, Near Nature Par

6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Just Southeast of Portland, Fenced Backyard, Fire Pit, Ping Pong, 15 Miles to Do, holiday rental in Gladstone

Just Southeast of Portland, Fenced Backyard, Fire Pit, Ping Pong, 15 Miles to Do

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Month-to-Month Portland | Lake Oswego 2 br Condo, holiday rental in Gladstone

Month-to-Month Portland | Lake Oswego 2 br Condo

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Couples Getaway! Walk to Rivers & Parks ~ Kitchenette ~ Private & Quiet Detached, holiday rental in Gladstone

Couples Getaway! Walk to Rivers & Parks ~ Kitchenette ~ Private & Quiet Detached

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Listed! Beautiful Views - Street Parking - BBQ - Mins to Shopping - 14 Mil, holiday rental in Gladstone

Newly Listed! Beautiful Views - Street Parking - BBQ - Mins to Shopping - 14 Mil

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Portland Home w/Yard 9 Miles to Downtown!, holiday rental in Gladstone

Charming Portland Home w/Yard 9 Miles to Downtown!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SE Park Ave 4B Retreat, Walk to MAX Station, holiday rental in Gladstone

SE Park Ave 4B Retreat, Walk to MAX Station

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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'The Bentley' - Spacious Seclusion in the Heart of It All, holiday rental in Gladstone

'The Bentley' - Spacious Seclusion in the Heart of It All

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Chic Simple Living Townhome, holiday rental in Gladstone

Chic Simple Living Townhome

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Excellent Location, Close to Parks, Groceries, Single Level Detached Retreat, 5, holiday rental in Gladstone

Excellent Location, Close to Parks, Groceries, Single Level Detached Retreat, 5

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Phenomenal Single Level Home Featuring Incredible Outdoor Golf Option w/ Gazebo,, holiday rental in Gladstone

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 Gladstone

Carman Garden Bungalow

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Single Level Southeast Portland Open Floor Plan Home + Large Covered Deck, Just, holiday rental in Gladstone

Single Level Southeast Portland Open Floor Plan Home + Large Covered Deck, Just

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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