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

Portland Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Portland holiday rentals

A spacious room with a large window, a sofa, armchairs, and a dining area.

1. Poconos Studio Suite w/ Kitchenette | Free Breakfast

Poconos Studio Suite w/ Kitchenette | Free Breakfast
East Stroudsburg
10.0 out of 10, Exceptional, (1 review)
The price is AU$219
includes taxes & fees
4 Oct - 5 Oct
Poconos Studio Suite w/ Kitchenette | Free Breakfast
A staircase leading to a door with a number plate, a bench, and a chair outside a building with windows and shutters.

2. 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, (81 reviews)
"Comfortable, well decorated, clean and more than reasonable cost."
United States
Peter M.
The price is AU$223
includes taxes & fees
22 Sept - 23 Sept
Cozy 1 bedroom apartment can sleep 4 queen size bed couch in living room
A modern kitchen with built-in appliances, a central island, pendant lighting, and a dining area with a wooden table and chairs.

3. Mountain Air - Hiking, Biking & River

Mountain Air - Hiking, Biking & River
East Stroudsburg
10.0 out of 10, Exceptional, (77 reviews)
"We had a great time!"
United States
Tony
The price is AU$365
includes taxes & fees
22 Sept - 23 Sept
Mountain Air - Hiking, Biking & River
A modern hotel room with a large bed, a sitting area with a sofa and chairs, a coffee table, and a view of the city through large windows.

4. 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 AU$523
includes taxes & fees
20 Sept - 21 Sept
Apt in the heart of Main Street
A modern living room with a fireplace, green sofa, and a large window.

5. Modern 4 Bedroom Home with Sauna and Game Room in Gated Lake Community

Modern 4 Bedroom Home with Sauna and Game Room in Gated Lake Community
East Stroudsburg
9.2 out of 10, Wonderful, (43 reviews)
"It was amazing and a great stay. I had a blast"
United States
Ryan G.
The price is AU$471
includes taxes & fees
17 Sept - 18 Sept
Modern 4 Bedroom Home with Sauna and Game Room in Gated Lake Community
A kitchen with white cabinets, a brick accent wall, pendant lighting, and a clock on the wall.

6. Very Welcoming

Very Welcoming
East Stroudsburg
7.6 out of 10, Good, (40 reviews)
"Nice overnight stay, and the host communicated well with us."
United States
Luke M.
The price is AU$293
includes taxes & fees
29 Sept - 30 Sept
Very Welcoming
A modern kitchen with a microwave, oven, and bar area. There is a dining area with a table set for four.

7. Magnolia House-Jacuzzi, Hiking, Biking & River

Magnolia House-Jacuzzi, Hiking, Biking & River
East Stroudsburg
9.8 out of 10, Exceptional, (92 reviews)
"Great place to stay"
United States
Nicola K.
The price is AU$402
includes taxes & fees
17 Sept - 18 Sept
Magnolia House-Jacuzzi, Hiking, Biking & River
Two Lexus cars parked in a lot with a building in the background.

8. 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.
The price is AU$428
includes taxes & fees
17 Sept - 18 Sept
Whitetail Retreat-Hiking, Biking & River adventure
A large building with a green roof, multiple windows, and a visible clock.

9. Pocono Mountains Escape - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace

Pocono Mountains Escape - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace
East Stroudsburg
10.0 out of 10, Exceptional, (6 reviews)
"Clean and welcoming stay. They gave thought about everything you need. "
United States
Lyn G.
Pocono Mountains Escape - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace
A wooden spa cabin with a hot tub, surrounded by snow, featuring a wooden door, string lights, and a small potted plant.

10. BLVE Cabin w/ Hot Tub,Sauna,Cold Plunge,Game Room Near Bushkill Falls & Shawnee

BLVE Cabin w/ Hot Tub,Sauna,Cold Plunge,Game Room Near Bushkill Falls & Shawnee
East Stroudsburg
9.0 out of 10, Wonderful, (24 reviews)
"The property was very clean and the amenities were great! The host were so helpful and friendly djring our entire stay and even allowed us to extend our time here! Absolutely amazing, a great place to stay for some peace and tranquility!"
United States
Sierra K.
The price is AU$556
includes taxes & fees
17 Sept - 18 Sept
BLVE Cabin w/ Hot Tub,Sauna,Cold Plunge,Game Room Near Bushkill Falls & Shawnee
A house with a porch decorated with string lights, a lawn, and outdoor seating.

11. The Nesting Place in the Pocono’s LLC Peaceful private country studio apartment

The Nesting Place in the Pocono’s LLC Peaceful private country studio apartment
Saylorsburg
9.6 out of 10, Exceptional, (59 reviews)
"This was a great place to stay! Clean and homey!"
United States
Jack L.
The price is AU$198
includes taxes & fees
23 Sept - 24 Sept
The Nesting Place in the Pocono’s LLC Peaceful private country studio apartment
A snow-covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and string lights.

12. Spacious Colonial Home with Hot Tub, Games, Lake Club & Top Local Attractions

Spacious Colonial Home with Hot Tub, Games, Lake Club & Top Local Attractions
East Stroudsburg
10.0 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay!"
United States
Deanna B.
The price is AU$1,154
includes taxes & fees
29 Sept - 30 Sept
Spacious Colonial Home with Hot Tub, Games, Lake Club & Top Local Attractions
A modern living room with a fireplace, black leather sofa, and large windows.

13. Modern BLVCK Cabin 3 W/ Hot Tub near Bushkill Fall/Shawnee/Poconos

Modern BLVCK Cabin 3 W/ Hot Tub near Bushkill Fall/Shawnee/Poconos
East Stroudsburg
9.4 out of 10, Exceptional, (9 reviews)
"Absolutely beautiful place! Host was amazing and had great communication the whole time! Can’t wait to go back "
United States
Kam R.
The price is AU$575
includes taxes & fees
30 Sept - 1 Oct
Modern BLVCK Cabin 3 W/ Hot Tub near Bushkill Fall/Shawnee/Poconos
A cozy living room with a fireplace, wooden walls, and a large TV.

14. 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
East Stroudsburg
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful place and the history was very communicatuve"
United States
Mark W.
The price is AU$419
includes taxes & fees
20 Sept - 21 Sept
Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub

15. Alpine Skylight · Modern Cozy Cabin in the Poconos Outdoor Retreat

Alpine Skylight · Modern Cozy Cabin in the Poconos Outdoor Retreat
East Stroudsburg
9.4 out of 10, Exceptional, (28 reviews)
"Had a great time!"
United States
Andrea W.
The price is AU$579
includes taxes & fees
29 Sept - 30 Sept
Alpine Skylight · Modern Cozy Cabin in the Poconos Outdoor Retreat
A gravel patio with a fire pit, outdoor seating, and a grill area by a pond.

16. Echo Valley Cottages

Echo Valley Cottages
3.0 star property
East Stroudsburg
8.6 out of 10, Excellent, (65 reviews)
"Country living with a beautiful outdoor pool and pond."
United States
Paulette
The price is AU$381
includes taxes & fees
30 Sept - 1 Oct
Echo Valley Cottages

17. Serene Pocono Mountains Home - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace

Serene Pocono Mountains Home - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace
East Stroudsburg
10.0 out of 10, Exceptional, (10 reviews)
"Very nice place and great location "
United States
Paul H.
The price is AU$458
includes taxes & fees
4 Oct - 5 Oct
Serene Pocono Mountains Home - 2 Bedroom, 2.5 Bath, private townhome with wood-burning fireplace
A rustic cabin with a stone foundation, a wooden deck, and a view of a calm lake surrounded by lush greenery.

18. Cabin, 2 Bunkbeds, Shared Bathroom

Cabin, 2 Bunkbeds, Shared Bathroom
Blairstown
The price is AU$327
includes taxes & fees
27 Sept - 28 Sept
Cabin, 2 Bunkbeds, Shared Bathroom

19. 2 Bedroom Cabin|East Stroudsburg

2 Bedroom Cabin|East Stroudsburg
East Stroudsburg
10.0 out of 10, Exceptional, (243 reviews)
"A great little spot!"
United States
Anonymous traveller
The price is AU$206
includes taxes & fees
20 Sept - 21 Sept
2 Bedroom Cabin|East Stroudsburg
A spacious living area with a fireplace, a dining area, and a kitchen.

20. Cozy House with a Lovely Treehouse. 7-Person Hot Tub. Pet Friendly. Hiking. Lake

Cozy House with a Lovely Treehouse. 7-Person Hot Tub. Pet Friendly. Hiking. Lake
East Stroudsburg
10.0 out of 10, Exceptional, (10 reviews)
"This is a wonderful house, well situated for adventures in the poconos and Delaware Water Gap."
United States
Jack C.
The price is AU$837
includes taxes & fees
28 Sept - 29 Sept
Cozy House with a Lovely Treehouse. 7-Person Hot Tub. Pet Friendly. Hiking. Lake
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

Best Western Plus Poconos Hotel

Best Western Plus Poconos Hotel

10/10 Excellent
"So great! Stood here for 4days 3 nights and we were very comfortable. Staff was friendly and everything was clean. The highlights were, that we were on the 2nd floor and all the amenities were right there for us. From the pool, the gym and even the breakfast room. We also had access to park right outside our window and walk out from our floor as if we were on the 1st. Then next highlight had to have been breakfast. It was a full spread that was well stocked and the attendant Jen was soo kind and welcoming. She was extremely helpful at breakfast that it made the whole experience effortless. She was the best staff experience we have seen in a long time. 5 stars for sure."
Bianca 3-night trip
Posted 19 hours ago
Best Western Plus Poconos Hotel

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, 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 favourite 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 depend 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 AU$198 per night. Entering your travel dates in the search wizard might find you 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 Brook Hollow Winery and Columcille Megalith Park.

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.