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Portland Vacation Rentals

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Our top choices for Portland vacation rentals

2.0 star property
10.0 out of 10, Exceptional, (10)
"Had an awesome time place is amazing "
United States
elizabeth m.
$749 nightly
The price is $817
Dec 16 - Dec 17
Total with taxes and fees
NEW! Large home in an upscale community close to all attractions! Hot Tub!
9.8 out of 10, Exceptional, (45)
"Great location. Great neighborhood "
United States
timothy m.
$225 nightly
The price is $245
Dec 16 - Dec 17
Total with taxes and fees
Rustic Retreat / Fireplace / Casino / Camelback - Close to everything!

Vacation Home in East Stroudsburg

Very Welcoming
8.4 out of 10, Very Good, (28)
"Another good overnight at nice property."
United States
Jay N.
$190 nightly
The price is $207
Dec 13 - Dec 14
Total with taxes and fees
Very Welcoming
2.0 star property
9.2 out of 10, Wonderful, (18)
"A very nice little house in a nice neighborhood!"
United States
Holly O.
$222 nightly
The price is $243
Dec 14 - Dec 15
Total with taxes and fees
Charming 2-bedroom house in serene Easton with WiFi, AC
9.4 out of 10, Exceptional, (34)
"It was a great stay! "
United States
Robert C.
$119 nightly
The price is $130
Dec 15 - Dec 16
Total with taxes and fees
The Nesting Place in the Pocono’s LLC Peaceful private country studio apartment
9.0 out of 10, Wonderful, (67)
"Nice place to stay for visit to Delaware water gap."
United States
Edward W.
$131 nightly
The price is $142
Dec 18 - Dec 19
Total with taxes and fees
Cozy 1 bedroom apartment can sleep 4 queen size bed couch in living room
9.8 out of 10, Exceptional, (38)
"Cleanliness is amazing and so close to amenities. Easy to check in and spacious "
United States
Eliana
$363 nightly
The price is $396
Dec 14 - Dec 15
Total with taxes and fees
Cabin by the Creek with private creek access -

Chalet in East Stroudsburg

Cozy Chalet on the lake
9.6 out of 10, Exceptional, (8)
"Place was very clean and organized"
United States
Yariel D.
$374 nightly
The price is $408
Dec 15 - Dec 16
Total with taxes and fees
Cozy Chalet on the lake
10.0 out of 10, Exceptional, (145)
"Great place!"
United States
Shakhzod O.
$479 nightly
The price is $521
Dec 14 - Dec 15
Total with taxes and fees
LUX Lakefront, Pool, Hot Tub, Game Room, FIFA 2026 Fully Loaded, Dock
8.8 out of 10, Excellent, (21)
"I was very pleased with the weekend in this house, excellent location."
United States
Rosa D.
$386 nightly
The price is $420
Dec 14 - Dec 15
Total with taxes and fees
Cozy Cabin, indoor pool, Ski On/Off camelback, snowtubing
10.0 out of 10, Exceptional, (204)
"Great for summer family vacation!"
United States
Christina P.
$521 nightly
The price is $566
Dec 17 - Dec 18
Total with taxes and fees
LUX Lakefront, FIFA 2026, Hot Tub, Pool, Games Ping Pong, Foosball

Vacation Home in Stroudsburg

Pocono dreams
10.0 out of 10, Exceptional, (37)
"Very clean and comfortable place! We loved our stay."
United States
Meah D.
$170 nightly
The price is $185
Dec 14 - Dec 15
Total with taxes and fees
Pocono dreams
10.0 out of 10, Exceptional, (2)
"Property was very nice. Location was remote but close to restaurants, casino and outlets."
United States
Amy C.
$549 nightly
The price is $598
Dec 23 - Dec 24
Total with taxes and fees
The Little Black Cabin - Sauna, Hot Tub, Fire Pit
9.8 out of 10, Exceptional, (86)
"The house was great, spacious, and very clean. Beds were very comfortable and the updated kitchen had everything you needed and more. Communication with the owner was easy, he was available to answer any questions with a quick response! "
United States
Jamie B.
$388 nightly
The price is $423
Dec 14 - Dec 15
Total with taxes and fees
Ski On/Off Camelback,Snowtubing,Pool,Waterparks,Paintball,Casino,Tennis,Zip-Line
9.8 out of 10, Exceptional, (86)
"Condo was clean, cute and close to so many attractions."
United States
perinda m.
$265 nightly
The price is $289
Dec 14 - Dec 15
Total with taxes and fees
Whitetail Retreat-Hiking, Biking & River adventure
9.6 out of 10, Exceptional, (18)
"Great place"
United States
Joe S.
$388 nightly
The price is $422
Dec 14 - Dec 15
Total with taxes and fees
Private Wooded Escape w/ Hot Tub + Fire Pit
10.0 out of 10, Exceptional, (75)
"As described and a very nice place to relax in the Poconos. Would stay here again."
United States
Marc M.
Mountain Air - Jacuzzi, Hiking, Biking & River; 15 min walk Shawnee Mt. Ski Area
9.8 out of 10, Exceptional, (82)
"Great for a weekend away!"
United States
Victoria K.
Magnolia House-Jacuzzi, Hiking, Biking & River, 15 min walk to Shawnee Ski Area
9.8 out of 10, Exceptional, (9)
"Relaxing, quiet, all the trappings one would like for a quick getaway. "
United States
Maxime A.
$489 nightly
The price is $506
Dec 16 - Dec 17
Total with taxes and fees
Luxurious Poconos Retreat~Hot Tub, Sauna, Games, Fire Pit, Pets Welcome!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Portland Hotel Reviews

Find out more about Portland

Everything you need to know about Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $130 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Portland?

Yes, we give you a choice of vacation rentals close to popular points of interest in Portland, or you can select a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals that Portland has to offer?

Pocono Mountain Villas by Exploria Resorts: This vacation home rental near Portland is located in the mountains and has an indoor pool, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and an oven.

What can I see and do in Portland?

Delaware River and Paulinskill River are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Camelback Ski Area and Brook Hollow Winery.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can stay in for several days or more in Portland. Vacation rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.