A calm river surrounded by lush green trees and hills under a clear blue sky.

Holiday Rentals in Portland

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Our top choices for Portland holiday rentals

Cozy 1 bedroom apartment can sleep 4 queen size bed couch in living room

Cozy 1 bedroom apartment can sleep 4 queen size bed couch in living room
East Stroudsburg
9.0 out of 10, Wonderful, (79 reviews)
"James was very responsive and made our stay very easy. "
United States
Kelly C.
The price is €142
includes taxes & fees
4 Aug - 5 Aug
Cozy 1 bedroom apartment can sleep 4 queen size bed couch in living room

Luxury Log Cabin w/ EV Charger & Mtn Views!

Luxury Log Cabin w/ EV Charger & Mtn Views!
Blairstown
10.0 out of 10, Exceptional, (14 reviews)
The price is €795
includes taxes & fees
2 Aug - 3 Aug
Luxury Log Cabin w/ EV Charger & Mtn Views!

Luxury Log Cabin w/ EV Charger & Mtn Views!

Luxury Log Cabin w/ EV Charger & Mtn Views!
3.0 star property
Blairstown
The price is €806
includes taxes & fees
2 Aug - 3 Aug
Luxury Log Cabin w/ EV Charger & Mtn Views!

Prime Location on Main Street

Prime Location on Main Street
Stroudsburg
10.0 out of 10, Exceptional, (7 reviews)
"Always great to visit here. Clean comfortable and convenient. "
United States
David P.
The price is €415
includes taxes & fees
23 Jul - 24 Jul
Prime Location on Main Street

Magnolia House-Jacuzzi, Hiking, Biking & River, 15 min walk to Shawnee Ski Area

Magnolia House-Jacuzzi, Hiking, Biking & River, 15 min walk to Shawnee Ski Area
East Stroudsburg
9.8 out of 10, Exceptional, (91 reviews)
"Great place to stay"
United States
Nicola K.
The price is €308
includes taxes & fees
22 Jul - 23 Jul
Magnolia House-Jacuzzi, Hiking, Biking & River, 15 min walk to Shawnee Ski Area

Whitetail Retreat-Hiking, Biking & River adventure

Whitetail Retreat-Hiking, Biking & River adventure
East Stroudsburg
9.8 out of 10, Exceptional, (88 reviews)
"The house was well equipped and very comfortable. The hosts were quick to answer questions and we had a great stay! "
United States
Amanda L.
Whitetail Retreat-Hiking, Biking & River adventure

Private Wooded Escape + Hot Tub + Fire Pit and Screen Porch

Private Wooded Escape + Hot Tub + Fire Pit and Screen Porch
East Stroudsburg
8.6 out of 10, Excellent, (30 reviews)
"EVERYTHING WAS FINE HOT TUB WAS RIGHT WHERE IT NEED TO BE ROOMS WHERE CLEAN AS WELL CABIN. GREAT PLACE TO SPEND TIME AAA"
United States
Yany F.
The price is €375
includes taxes & fees
22 Jul - 23 Jul
Private Wooded Escape + Hot Tub + Fire Pit and Screen Porch

Poconos Studio Suite w/ Kitchenette | Free Breakfast

Poconos Studio Suite w/ Kitchenette | Free Breakfast
East Stroudsburg
The price is €139
includes taxes & fees
16 Aug - 17 Aug
Poconos Studio Suite w/ Kitchenette | Free Breakfast

Cabin, 2 Bunkbeds, Shared Bathroom

Cabin, 2 Bunkbeds, Shared Bathroom
Blairstown
The price is €209
includes taxes & fees
26 Jul - 27 Jul
Cabin, 2 Bunkbeds, Shared Bathroom

2 ACRE POCONO HOUSE • PRIVATE POOL • TENNIS COURT • BACKYARD • PATIO

2 ACRE POCONO HOUSE • PRIVATE POOL • TENNIS COURT • BACKYARD • PATIO
East Stroudsburg
9.0 out of 10, Wonderful, (16 reviews)
"Outside space was amazing! Relaxing, quiet location!"
United States
Kimberley C.
The price is €855
includes taxes & fees
22 Jul - 23 Jul
2 ACRE POCONO HOUSE • PRIVATE POOL • TENNIS COURT • BACKYARD • PATIO

Echo Valley Cottages

Echo Valley Cottages
3.0 star property
East Stroudsburg
8.6 out of 10, Excellent, (63 reviews)
"Everything was good from the start. Served my purpose perfectly. Close enough to the race track but still private and serene enough for a getaway. The host was great and personable also."
United States
Michael
The price is €249
includes taxes & fees
6 Aug - 7 Aug
Echo Valley Cottages

Cabin with hot tub and pool at Pocono Mountains -Shawnee/Camelback

Cabin with hot tub and pool at Pocono Mountains -Shawnee/Camelback
East Stroudsburg
9.6 out of 10, Exceptional, (26 reviews)
"This was a great little getaway—very clean and tucked away in a peaceful location. We’ll definitely be coming back and will be sharing this little weekend hideout with family and friends."
United States
Alan C.
The price is €471
includes taxes & fees
22 Jul - 23 Jul
Cabin with hot tub and pool at Pocono Mountains -Shawnee/Camelback

Very Welcoming

Very Welcoming
East Stroudsburg
7.6 out of 10, Good, (39 reviews)
"Nice overnight stay, and the host communicated well with us."
United States
Luke M.
The price is €207
includes taxes & fees
20 Aug - 21 Aug
Very Welcoming

The Nook - lodge cabin with hot tub at Shawnee Mtn

The Nook - lodge cabin with hot tub at Shawnee Mtn
East Stroudsburg
9.8 out of 10, Exceptional, (25 reviews)
"Great property with lots of information for local activities, we loved watching a movie by the fireplace! The queen bed was very comfortable and loved being able to make coffee in the morning. "
United States
Cassidy K.
The price is €408
includes taxes & fees
30 Jul - 31 Jul
The Nook - lodge cabin with hot tub at Shawnee Mtn

Apt in the heart of Main Street

Apt in the heart of Main Street
Stroudsburg
10.0 out of 10, Exceptional, (4 reviews)
"Great downtown location close to shopping and restaurants. The apartment is very spacious and beautifully decorated! They had everything that we needed, including a laundry machine which was very convenient. "
United States
Eric R.
The price is €382
includes taxes & fees
28 Jul - 29 Jul
Apt in the heart of Main Street

Private Heated Pool! Hot Tub, Fire Pit, Game Room!

Private Heated Pool! Hot Tub, Fire Pit, Game Room!
East Stroudsburg
Private Heated Pool! Hot Tub, Fire Pit, Game Room!

Cozy Lakefront Home w/ Game Room, Hot Tub, Fire Pit, & Boats

Cozy Lakefront Home w/ Game Room, Hot Tub, Fire Pit, & Boats
East Stroudsburg
The price is €865
includes taxes & fees
24 Jul - 25 Jul
Cozy Lakefront Home w/ Game Room, Hot Tub, Fire Pit, & Boats

Escape to the Poconos | Hot Tub, Sauna, Mini-Golf

Escape to the Poconos | Hot Tub, Sauna, Mini-Golf
East Stroudsburg
The price is €760
includes taxes & fees
22 Jul - 23 Jul
Escape to the Poconos | Hot Tub, Sauna, Mini-Golf

Lakefront Luxury Retreat w/ Hot Tub, Sauna, Jacuzzi, Kayaks & Fishing

Lakefront Luxury Retreat w/ Hot Tub, Sauna, Jacuzzi, Kayaks & Fishing
East Stroudsburg
Lakefront Luxury Retreat w/ Hot Tub, Sauna, Jacuzzi, Kayaks & Fishing

Sauna | Firepit | Hot Tub | Hike

Sauna | Firepit | Hot Tub | Hike
East Stroudsburg
Sauna | Firepit | Hot Tub | Hike
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as €249 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday 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 holiday.

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 holiday rentals in Portland?

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing stay.

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

Pocono Mountain Villas by Exploria Resorts by Sonesta: This holiday home rental outside of Portland is located in the mountains, and has an indoor pool, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

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 wider area, you’ll find Columcille Megalith Park and Worthington State Forest.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.