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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Portland holiday rentals

A modern kitchen with built-in appliances, a central island, pendant lighting, and a dining area with a wooden table and chairs.

1. 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
Mountain Air - Hiking, Biking & River
A spacious room with a large window, a sofa, armchairs, and a dining area.

2. 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 HK$883
HK$1,134 total
includes taxes & fees
25 Oct - 26 Oct
Poconos Studio Suite w/ Kitchenette | Free Breakfast
A wood deck with a glass-top fire pit.

3. Rustic Cedar Cabin Getaway near Poconos Modern Look + Indoor Pool + Hot Tub /420

Rustic Cedar Cabin Getaway near Poconos Modern Look + Indoor Pool + Hot Tub /420
Blairstown
10.0 out of 10, Exceptional, (2 reviews)
"had a great stay !! very cozy and spacious! will definitely book again for a longer time!"
United States
Natasha
The price is HK$1,958
HK$2,437 total
includes taxes & fees
12 Oct - 13 Oct
Rustic Cedar Cabin Getaway near Poconos Modern Look + Indoor Pool + Hot Tub /420
A modern kitchen with a microwave, oven, and bar area. There is a dining area with a table set for four.

4. 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.
Magnolia House-Jacuzzi, 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.

5. 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 HK$1,290
HK$3,109 total
includes taxes & fees
4 Oct - 5 Oct
Apt in the heart of Main Street
A staircase leading to a door with a number plate, a bench, and a chair outside a building with windows and shutters.

6. 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, (82 reviews)
"Comfortable, well decorated, clean and more than reasonable cost."
United States
Peter M.
The price is HK$427
HK$1,235 total
includes taxes & fees
8 Oct - 9 Oct
Cozy 1 bedroom apartment can sleep 4 queen size bed couch in living room
Two Lexus cars parked in a lot with a building in the background.

7. 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
A house with a porch decorated with string lights, a lawn, and outdoor seating.

8. 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, (60 reviews)
"This was a great place to stay! Clean and homey!"
United States
Jack L.
The price is HK$847
HK$1,095 total
includes taxes & fees
4 Oct - 5 Oct
The Nesting Place in the Pocono’s LLC Peaceful private country studio apartment
A gravel patio with a fire pit, outdoor seating, and a grill area by a pond.

9. 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 HK$1,477
HK$2,277 total
includes taxes & fees
4 Oct - 5 Oct
Echo Valley Cottages
A rustic cabin with a stone foundation, a wooden deck, and a view of a calm lake surrounded by lush greenery.

10. Cabin, 2 Bunkbeds, Shared Bathroom

Cabin, 2 Bunkbeds, Shared Bathroom
Blairstown
The price is HK$1,514
HK$1,834 total
includes taxes & fees
1 Oct - 2 Oct
Cabin, 2 Bunkbeds, Shared Bathroom
A snow-covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and string lights.

11. 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 HK$770
HK$6,577 total
includes taxes & fees
6 Oct - 7 Oct
Spacious Colonial Home with Hot Tub, Games, Lake Club & Top Local Attractions
A modern living room with a fireplace, green sofa, and a large window.

12. 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, (46 reviews)
"It was amazing and a great stay. I had a blast"
United States
Ryan G.
The price is HK$408
HK$2,577 total
includes taxes & fees
1 Oct - 2 Oct
Modern 4 Bedroom Home with Sauna and Game Room in Gated Lake Community
Holiday Home Facilities and Services

13. 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 HK$787
HK$1,023 total
includes taxes & fees
5 Oct - 6 Oct
2 Bedroom Cabin|East Stroudsburg
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, (29 reviews)
"Beautiful place and the history was very communicatuve"
United States
Mark W.
The price is HK$1,165
HK$2,339 total
includes taxes & fees
4 Oct - 5 Oct
Pocono Mountains Retreat - 2 Bedroom, 2 Bath, private townhome with wood-burning fireplace and jacuzzi tub
A snowy outdoor area with a fire pit and people gathered around.

15. 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, (26 reviews)
"Nicely off the beaten path place with a great backyard view of nature."
United States
Kaitlyn D.
The price is HK$1,240
HK$2,206 total
includes taxes & fees
4 Oct - 5 Oct
The Nook - lodge cabin with hot tub at Shawnee Mtn
Pool

16. 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 HK$981
HK$3,181 total
includes taxes & fees
4 Oct - 5 Oct
Alpine Skylight · Modern Cozy Cabin in the Poconos Outdoor Retreat
A water park with multiple water play areas and covered seating areas.

17. Luxury 5BR Family Retreat | Hot Tub | Game Room | 2 Fire Pits | Resort Amenities

Luxury 5BR Family Retreat | Hot Tub | Game Room | 2 Fire Pits | Resort Amenities
East Stroudsburg
10.0 out of 10, Exceptional, (14 reviews)
"Lovely home and Frank was awesome! Very quick to respond!"
United States
Janice A.
The price is HK$839
HK$6,036 total
includes taxes & fees
4 Oct - 5 Oct
Luxury 5BR Family Retreat | Hot Tub | Game Room | 2 Fire Pits | Resort Amenities
A wooden spa cabin with a hot tub, surrounded by snow, featuring a wooden door, string lights, and a small potted plant.

18. 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
9.2 out of 10, Wonderful, (25 reviews)
"We had a lovely vacation!"
United States
Nancy D.
The price is HK$882
HK$3,253 total
includes taxes & fees
4 Oct - 5 Oct
BLVE Cabin w/ Hot Tub,Sauna,Cold Plunge,Game Room Near Bushkill Falls & Shawnee
A living room with a green sofa, a wooden coffee table, and a TV on a wooden cabinet. There is a dining area with a table and chairs, and a large window providing natural light.

19. Prime Location on Main Street

Prime Location on Main Street
Stroudsburg
10.0 out of 10, Exceptional, (8 reviews)
"Always great to visit here. Clean comfortable and convenient. "
United States
David P.
The price is HK$1,121
HK$3,317 total
includes taxes & fees
1 Oct - 2 Oct
Prime Location on Main Street
A modern living room with a fireplace, black leather sofa, and large windows.

20. 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, (10 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 HK$956
HK$3,351 total
includes taxes & fees
4 Oct - 5 Oct
Modern BLVCK Cabin 3 W/ Hot Tub near Bushkill Fall/Shawnee/Poconos
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

Mount Airy Casino Resort - Adults Only 21+

Mount Airy Casino Resort - Adults Only 21+

8/10 Good
"Hotel was clean staff was nice. Wish they had a hot tub and pool was warmer."
Ricky 1-night trip
Posted 2 hours ago
Mount Airy Casino Resort - Adults Only 21+

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

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.