Vacation rentals in Portland, PA

127 available vacation rental offers

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Best vacation rentals and Airbnb offers in Portland, PA

Very Welcoming - Portland, PA

Very Welcoming

Holiday Home, Portland

Very Welcoming is a holiday home in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Very Welcoming

Very Welcoming is a holiday home 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 $890.

From$127/night
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Shawnee Ski Mountain View Jacuzzi Townhouse - Portland, PA

Shawnee Ski Mountain View Jacuzzi Townhouse

Holiday Home, Portland

Shawnee Ski Mountain View Jacuzzi Townhouse is a holiday home in Portland. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Shawnee Ski Mountain View Jacuzzi Townhouse

Shawnee Ski Mountain View Jacuzzi Townhouse is a holiday home in Portland. 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, hot tub, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,069.

From$153/night
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Fish & Hike: Lakeside Poconos Retreat, Unit 3 - Portland, PA

Fish & Hike: Lakeside Poconos Retreat, Unit 3

Apartment, Portland

Fish & Hike: Lakeside Poconos Retreat, Unit 3 is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Fish & Hike: Lakeside Poconos Retreat, Unit 3

Fish & Hike: Lakeside Poconos Retreat, Unit 3 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 $1,142.

From$163/night
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Fish & Hike: Lakeside Poconos Retreat, Unit 4 - Portland, PA

Fish & Hike: Lakeside Poconos Retreat, Unit 4

Apartment, Portland

Fish & Hike: Lakeside Poconos Retreat, Unit 4 is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Fish & Hike: Lakeside Poconos Retreat, Unit 4

Fish & Hike: Lakeside Poconos Retreat, Unit 4 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 $1,147.

From$164/night
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Vacation rentals with a pool in Portland, PA

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

Pocono Mountain Villas MOD Collection by Sonesta - Portland, PA

Pocono Mountain Villas MOD Collection by Sonesta

Holiday Home, Portland

Pocono Mountain Villas MOD Collection by Sonesta is a holiday home in Portland, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pocono Mountain Villas MOD Collection by Sonesta

Pocono Mountain Villas MOD Collection by Sonesta is a holiday home in Portland, with 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $858.

From$82/night
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Sage Grove Sanctuary | Hot Tub | Modern | BBQ - Portland, PA

Sage Grove Sanctuary | Hot Tub | Modern | BBQ

Holiday Home, Portland

Sage Grove Sanctuary · Hot Tub · Modern · BBQ is a holiday home 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 Sage Grove Sanctuary | Hot Tub | Modern | BBQ

Sage Grove Sanctuary · Hot Tub · Modern · BBQ is a holiday home 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, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,615.

From$231/night
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Cherry Valley Manor Luxury Bed and Breakfast - Portland, PA

Cherry Valley Manor Luxury Bed and Breakfast

B & B, Portland

Cherry Valley Manor Luxury Bed and Breakfast is a b & b in Portland, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cherry Valley Manor Luxury Bed and Breakfast

Cherry Valley Manor Luxury Bed and Breakfast is a b & b in Portland, with 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 breakfast, pool, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,737.

From$359/night
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Cherry Valley Manor - Portland, PA

Cherry Valley Manor

B & B, Portland

Cherry Valley Manor is a b & b in Portland, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Cherry Valley Manor

Cherry Valley Manor is a b & b in Portland, with 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, free breakfast, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,195.

From$399/night
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Vacation rentals with parking in Portland, PA

Find vacation rentals that make arriving by car easier.

Deck & Gas Grill: Modern East Stroudsburg Home! - Portland, PA

Deck & Gas Grill: Modern East Stroudsburg Home!

Holiday Home, Portland

Deck & Gas Grill: Modern East Stroudsburg Home! is a holiday home in Portland, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About Deck & Gas Grill: Modern East Stroudsburg Home!

Deck & Gas Grill: Modern East Stroudsburg Home! is a holiday home in Portland, with pet-friendly space, outdoor space, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,950.

From$202/night
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Cabin, Double Bed, 2 Bunks, Shared Bathroom - Portland, PA

Cabin, Double Bed, 2 Bunks, Shared Bathroom

Cabin, Portland

Cabin, Double Bed, 2 Bunks, Shared Bathroom is a cabin in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cabin, Double Bed, 2 Bunks, Shared Bathroom

Cabin, Double Bed, 2 Bunks, Shared Bathroom is a cabin 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,536.

From$219/night
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2-bedroom apartment above coffee shop in the heart of downtown East Stroudsburg. - Portland, PA

2-bedroom apartment above coffee shop in the heart of downtown East Stroudsburg.

Apartment, Portland

2-bedroom apartment above coffee shop in the heart of downtown East Stroudsburg. is a apartment in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 2-bedroom apartment above coffee shop in the heart of downtown East Stroudsburg.

2-bedroom apartment above coffee shop in the heart of downtown East Stroudsburg. is a apartment 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,736.

From$248/night
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Chic Retreat Downtown Stroudsburg | 3BR+Sleeps 10 - Portland, PA

Chic Retreat Downtown Stroudsburg | 3BR+Sleeps 10

Apartment, Portland

Chic Retreat Downtown Stroudsburg · 3BR+Sleeps 10 is a apartment 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 Chic Retreat Downtown Stroudsburg | 3BR+Sleeps 10

Chic Retreat Downtown Stroudsburg · 3BR+Sleeps 10 is a apartment 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 $1,809.

From$258/night
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Pet-friendly vacation rentals in Portland, PA

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

Pocono Mountains Hideaway - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace - Portland, PA

Pocono Mountains Hideaway - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace

Holiday Home, Portland

Pocono Mountains Hideaway - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace is a holiday home in Portland, with pet-friendly space, parking, and kitchen access. This stay…

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About Pocono Mountains Hideaway - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace

Pocono Mountains Hideaway - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace 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 $1,527.

From$218/night
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Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub - Portland, PA

Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub

Holiday Home, Portland

Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub is a holiday home in Portland, with pet-friendly space, parking, and kitchen…

Read more

About Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub

Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub 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 $1,544.

From$221/night
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Walkable Abode in Stroudsburg's Business District! - Portland, PA

Walkable Abode in Stroudsburg's Business District!

Apartment, Portland

Walkable Abode in Stroudsburg's Business District! 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 Walkable Abode in Stroudsburg's Business District!

Walkable Abode in Stroudsburg's Business District! 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 $2,371.

From$267/night
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Peaceful home in mount bethel, PA - Portland, PA

Peaceful home in mount bethel, PA

Holiday Home, Portland

Peaceful home in mount bethel, PA 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,…

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About Peaceful home in mount bethel, PA

Peaceful home in mount bethel, PA 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 $2,286.

From$327/night
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Vacation rentals with a kitchen in Portland, PA

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

Scenic Cabin by Bushkill Falls & Shawnee w/Hot Tub - Portland, PA

Scenic Cabin by Bushkill Falls & Shawnee w/Hot Tub

Cabin, Portland

Scenic Cabin by Bushkill Falls & Shawnee w/Hot Tub is a cabin 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 Scenic Cabin by Bushkill Falls & Shawnee w/Hot Tub

Scenic Cabin by Bushkill Falls & Shawnee w/Hot Tub is a cabin 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,630.

From$233/night
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Whitetail Retreat-Hiking, Biking & River adventure - Portland, PA

Whitetail Retreat-Hiking, Biking & River adventure

Holiday Home, Portland

Whitetail Retreat-Hiking, Biking & River adventure is a holiday home in Portland, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Whitetail Retreat-Hiking, Biking & River adventure

Whitetail Retreat-Hiking, Biking & River adventure is a holiday home in Portland, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,633.

From$233/night
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Deck & Gas Grill: Modern East Stroudsburg Home! - Portland, PA

Deck & Gas Grill: Modern East Stroudsburg Home!

Cottage, Portland

Deck & Gas Grill: Modern East Stroudsburg Home! is a cottage in Portland, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Deck & Gas Grill: Modern East Stroudsburg Home!

Deck & Gas Grill: Modern East Stroudsburg Home! is a cottage 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,019.

From$237/night
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Walkable Abode in Stroudsburg's Business District! - Portland, PA

Walkable Abode in Stroudsburg's Business District!

Holiday Home, Portland

Walkable Abode in Stroudsburg's Business District! is a holiday home in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Walkable Abode in Stroudsburg's Business District!

Walkable Abode in Stroudsburg's Business District! 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,941.

From$277/night
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Family-friendly vacation rentals in Portland, PA

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

Game Room, Fire Pit: Family-Friendly Poconos Haven - Portland, PA

Game Room, Fire Pit: Family-Friendly Poconos Haven

Holiday Home, Portland

Game Room, Fire Pit: Family-Friendly Poconos Haven is a holiday home in Portland, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Game Room, Fire Pit: Family-Friendly Poconos Haven

Game Room, Fire Pit: Family-Friendly Poconos Haven is a holiday home in Portland, with parking 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 wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,704.

From$164/night
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Game Room, Fire Pit: Family-friendly Poconos Haven - Portland, PA

Game Room, Fire Pit: Family-friendly Poconos Haven

Cottage, Portland

Game Room, Fire Pit: Family-friendly Poconos Haven is a cottage 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 Game Room, Fire Pit: Family-friendly Poconos Haven

Game Room, Fire Pit: Family-friendly Poconos Haven is a cottage 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 $1,916.

From$218/night
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Game Room, Fire Pit: Family-Friendly Poconos Haven - Portland, PA

Game Room, Fire Pit: Family-Friendly Poconos Haven

Holiday Home, Portland

Game Room, Fire Pit: Family-Friendly Poconos Haven is a holiday home in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Game Room, Fire Pit: Family-Friendly Poconos Haven

Game Room, Fire Pit: Family-Friendly Poconos Haven 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,628.

From$233/night
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Shawnee Mountain 2bdr kids friendly townhouse 3 minutes away from slopes - Portland, PA

Shawnee Mountain 2bdr kids friendly townhouse 3 minutes away from slopes

Holiday Home, Portland

Shawnee Mountain 2bdr kids friendly townhouse 3 minutes away from slopes is a holiday home in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Shawnee Mountain 2bdr kids friendly townhouse 3 minutes away from slopes

Shawnee Mountain 2bdr kids friendly townhouse 3 minutes away from slopes 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,670.

From$239/night
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