Vacation rentals in Portland, IL

176 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Portland, IL

Contemporary dog-friendly studio w/ cable, WiFi, and private balcony - Portland, IL

Contemporary dog-friendly studio w/ cable, WiFi, and private balcony

Apartment, Portland

Contemporary dog-friendly studio w/ cable, WiFi, and private balcony is a apartment in Portland, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a…

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About Contemporary dog-friendly studio w/ cable, WiFi, and private balcony

Contemporary dog-friendly studio w/ cable, WiFi, and private balcony is a apartment in Portland, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $941.

From$76/night
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Artful, Rustic Studio w/ 5-star shower---Sustainable Ethic, 20 min to Downtown - Portland, IL

Artful, Rustic Studio w/ 5-star shower---Sustainable Ethic, 20 min to Downtown

Holiday Home, Portland

Artful, Rustic Studio w/ 5-star shower---Sustainable Ethic, 20 min to Downtown is a holiday home in Portland, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Artful, Rustic Studio w/ 5-star shower---Sustainable Ethic, 20 min to Downtown

Artful, Rustic Studio w/ 5-star shower---Sustainable Ethic, 20 min to Downtown is a holiday home in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $992.

From$88/night
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Cozy, quiet & private loft studio - Portland, IL

Cozy, quiet & private loft studio

Apartment, Portland

Cozy, quiet & private loft studio is a apartment in Portland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy, quiet & private loft studio

Cozy, quiet & private loft studio is a apartment in Portland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,043.

From$102/night
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#StayInMyDistrict Overlook Backyard Tiny Suite - Portland, IL

#StayInMyDistrict Overlook Backyard Tiny Suite

Holiday Home, Portland

#StayInMyDistrict Overlook Backyard Tiny Suite is a holiday home in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About #StayInMyDistrict Overlook Backyard Tiny Suite

#StayInMyDistrict Overlook Backyard Tiny Suite is a holiday home in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,122.

From$103/night
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Browse Vacation Rentals with a Pool in Portland, IL

Add a pool to the search when you want an easy place to cool off between outings.

Delightful apartment with AC in charming Lake Oswego - Portland, IL

Delightful apartment with AC in charming Lake Oswego

Apartment, Portland

Delightful apartment with AC in charming Lake Oswego is a apartment in Portland, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Delightful apartment with AC in charming Lake Oswego

Delightful apartment with AC in charming Lake Oswego is a apartment in Portland, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,105.

From$114/night
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Stylish, New & Clean 1b apt w/ King Bed+Pool+Gym+Parking - Portland, IL

Stylish, New & Clean 1b apt w/ King Bed+Pool+Gym+Parking

Apartment, Portland

Stylish, New & Clean 1b apt w/ King Bed+Pool+Gym+Parking is a apartment in Portland, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for…

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About Stylish, New & Clean 1b apt w/ King Bed+Pool+Gym+Parking

Stylish, New & Clean 1b apt w/ King Bed+Pool+Gym+Parking is a apartment in Portland, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,355.

From$120/night
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NEW! King Bed, 600mbps +4K TVs in the Garden Apt - Portland, IL

NEW! King Bed, 600mbps +4K TVs in the Garden Apt

Apartment, Portland

NEW! King Bed, 600mbps +4K TVs in the Garden Apt is a apartment in Portland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW! King Bed, 600mbps +4K TVs in the Garden Apt

NEW! King Bed, 600mbps +4K TVs in the Garden Apt is a apartment in Portland, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,737.

From$135/night
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Wonderfully Appointed Home in Day Ranch Style Layout, Pet Friendly, Pool Table, Sauna, Deck, BBQ - Portland, IL

Wonderfully Appointed Home in Day Ranch Style Layout, Pet Friendly, Pool Table, Sauna, Deck, BBQ

Holiday Home, Portland

Wonderfully Appointed Home in Day Ranch Style Layout, Pet Friendly, Pool Table, Sauna, Deck, BBQ is a holiday home in Portland, with pet-friendly space, pool access, and outdoor space. This…

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About Wonderfully Appointed Home in Day Ranch Style Layout, Pet Friendly, Pool Table, Sauna, Deck, BBQ

Wonderfully Appointed Home in Day Ranch Style Layout, Pet Friendly, Pool Table, Sauna, Deck, BBQ is a holiday home in Portland, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,156.

From$181/night
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Best Portland, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland - Portland, IL

Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland

Condo, Portland

Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland is a condo in Portland, with parking. This stay gives travelers a comfortable base for…

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About Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland

Bamboo Haven: Tranquil Studio Nestled Off-Street with Chic Zen-Inspired Decor, 7 Miles to Portland is a condo in Portland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,124.

From$108/night
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Roseway Retreat, a relaxing urban escape - Portland, IL

Roseway Retreat, a relaxing urban escape

Holiday Home, Portland

Roseway Retreat, a relaxing urban escape is a holiday home in Portland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Roseway Retreat, a relaxing urban escape

Roseway Retreat, a relaxing urban escape is a holiday home in Portland, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,135.

From$112/night
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Mid-Century Hideaway, Near Forest Park - Portland, IL

Mid-Century Hideaway, Near Forest Park

Holiday Home, Portland

Mid-Century Hideaway, Near Forest Park is a holiday home in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Mid-Century Hideaway, Near Forest Park

Mid-Century Hideaway, Near Forest Park is a holiday home in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,351.

From$135/night
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King Comfort & City Access - Portland, IL

King Comfort & City Access

Apartment, Portland

King Comfort & City Access is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About King Comfort & City Access

King Comfort & City Access is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,497.

From$150/night
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Best Pet-Friendly Vacation Rentals in Portland, IL

Bring your pet along with stays that welcome four-legged travelers.

Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower - Portland, IL

Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower

Apartment, Portland

Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower

Artful, Rustic Backyard Cabin-Sustainable Ethic, Downtown 20 Min, 5-Star Shower is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,224.

From$115/night
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Tiny Retreat • Walk to Bars, Food & Local Art - Portland, IL

Tiny Retreat • Walk to Bars, Food & Local Art

Apartment, Portland

Tiny Retreat · Walk to Bars, Food & Local Art is a apartment in Portland, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Tiny Retreat • Walk to Bars, Food & Local Art

Tiny Retreat · Walk to Bars, Food & Local Art is a apartment in Portland, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,342.

From$142/night
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Modern Hawthorne Studio - Food Carts & Local Shops - Portland, IL

Modern Hawthorne Studio - Food Carts & Local Shops

Apartment, Portland

Modern Hawthorne Studio - Food Carts & Local Shops is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Modern Hawthorne Studio - Food Carts & Local Shops

Modern Hawthorne Studio - Food Carts & Local Shops is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,350.

From$145/night
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Kerns Urban Cabin • New Build • AC • Walkable - Portland, IL

Kerns Urban Cabin • New Build • AC • Walkable

Apartment, Portland

Kerns Urban Cabin · New Build · AC · Walkable is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Kerns Urban Cabin • New Build • AC • Walkable

Kerns Urban Cabin · New Build · AC · Walkable is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,541.

From$168/night
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Best Portland, IL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Two Rivers Tiny Red Gem - Portland, IL

Two Rivers Tiny Red Gem

Guest House, Portland

Two Rivers Tiny Red Gem is a guest house in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Two Rivers Tiny Red Gem

Two Rivers Tiny Red Gem is a guest house in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,170.

From$118/night
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#StayinMyDistrict Kenton Private Guest House - Portland, IL

#StayinMyDistrict Kenton Private Guest House

Holiday Home, Portland

#StayinMyDistrict Kenton Private Guest House is a holiday home in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About #StayinMyDistrict Kenton Private Guest House

#StayinMyDistrict Kenton Private Guest House is a holiday home in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,442.

From$135/night
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Tiny House • Close to Food, Coffee & Art - Portland, IL

Tiny House • Close to Food, Coffee & Art

Apartment, Portland

Tiny House · Close to Food, Coffee & Art is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Tiny House • Close to Food, Coffee & Art

Tiny House · Close to Food, Coffee & Art is a apartment in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,333.

From$144/night
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The Tiny Farmhouse on Alberta - Portland, IL

The Tiny Farmhouse on Alberta

Holiday Home, Portland

The Tiny Farmhouse on Alberta is a holiday home in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Tiny Farmhouse on Alberta

The Tiny Farmhouse on Alberta is a holiday home in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,354.

From$146/night
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Our Favorite Family-Friendly Vacation Rentals in Portland, IL

Plan a trip with stays that give families more room to spread out.

Mossy Cobbles: Romantic Cottage in a Wooded Setting - Portland, IL

Mossy Cobbles: Romantic Cottage in a Wooded Setting

Cottage, Portland

Mossy Cobbles: Romantic Cottage in a Wooded Setting is a cottage in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mossy Cobbles: Romantic Cottage in a Wooded Setting

Mossy Cobbles: Romantic Cottage in a Wooded Setting is a cottage in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,076.

From$115/night
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Charming Fireplace! Walk to Alberta Arts SilverStar cottage in NE Portland. - Portland, IL

Charming Fireplace! Walk to Alberta Arts SilverStar cottage in NE Portland.

Guest House, Portland

Charming Fireplace! Walk to Alberta Arts SilverStar cottage in NE Portland. is a guest house in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Charming Fireplace! Walk to Alberta Arts SilverStar cottage in NE Portland.

Charming Fireplace! Walk to Alberta Arts SilverStar cottage in NE Portland. is a guest house in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,261.

From$128/night
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Hidden Gem Secluded Garden Oasis Family Getaway - Portland, IL

Hidden Gem Secluded Garden Oasis Family Getaway

Holiday Home, Portland

Hidden Gem Secluded Garden Oasis Family Getaway is a holiday home in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Hidden Gem Secluded Garden Oasis Family Getaway

Hidden Gem Secluded Garden Oasis Family Getaway is a holiday home in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,311.

From$134/night
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Immaculate Detached Cottage - Walk to MAX, Drinks, Dining, 3 Miles to Dwntwn, Full Kitchen & BBQ - Portland, IL

Immaculate Detached Cottage - Walk to MAX, Drinks, Dining, 3 Miles to Dwntwn, Full Kitchen & BBQ

Cottage, Portland

Immaculate Detached Cottage - Walk to MAX, Drinks, Dining, 3 Miles to Dwntwn, Full Kitchen & BBQ is a cottage in Portland, with parking and kitchen access. This stay gives travelers a…

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About Immaculate Detached Cottage - Walk to MAX, Drinks, Dining, 3 Miles to Dwntwn, Full Kitchen & BBQ

Immaculate Detached Cottage - Walk to MAX, Drinks, Dining, 3 Miles to Dwntwn, Full Kitchen & BBQ is a cottage in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,709.

From$139/night
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