The Best Portland, PA Chalets from $267

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Our top choices for Portland chalets

A snow-covered house with a car parked in front, surrounded by trees.

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

East Stroudsburg

Jack C.

$552 nightly

Dec 2 - Dec 3

Total with taxes and fees

A hot tub on a wooden deck with a wooden house in the background.

2. NEW! Crestwood Hideaway - Hot Tub, Dog-Friendly, Walk to Lake, EV Charger

East Stroudsburg

$522 nightly

Nov 30 - Dec 1

Total with taxes and fees

A cabin with a wooden deck, large windows, and a chimney.

3. Award-Winning A-Frame | Hot Tub | Lakes | Firepit

East Stroudsburg

Roxanne D.

$494 nightly

Nov 9 - Nov 10

Total with taxes and fees

An outdoor deck with a glass-top fire pit, a cushioned seating area, and a view of a forested area.

4. Chalet Near Camelback, Ski, Game Room, Hot Tub, Fire Pits, Hiking, Pet, Karaoke!

East Stroudsburg

$567 nightly

Nov 11 - Nov 12

Total with taxes and fees

A wooden cabin with a deck, benches, a fire pit, and string lights.

5. Hot Tub | Cold Plunge | Sauna | Firepit

East Stroudsburg

$535 nightly

Nov 5 - Nov 6

Total with taxes and fees

A deck with outdoor furniture, a fire feature, and string lights.

6. Hot tub/Cold Plunge/Sauna/Pools/Lakes

Saw Creek

Lauren M.

$495 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden deck with a chair and a decorative lamp, overlooking a forest and a pool area.

7. Japanese Soaking Tub | Hot Tub | Lakes | Sleeps 7

East Stroudsburg

A covered deck with wooden railings, outdoor seating, and a view of a forest.

8. Pocono Sleep 16 Sauna Hot Tub + Private Acre + AC + King + Bunk Beds + Spa Bath

Cresco

Cassie F.

$896 nightly

Nov 9 - Nov 10

Total with taxes and fees

A spacious bedroom with a large bed, a bench, a chair, and a view of the outdoors through a large window.

9. Romantic Couples Suite in the Poconos with Jetted Tub

Stroudsburg

$257 nightly

Nov 5 - Nov 6

Total with taxes and fees

A cabin with a deck and stairs, surrounded by trees.

10. 5BR Spa Chalet - Hot Tub, Pool Table, Loft

East Stroudsburg

"We had a wonderful stay here and truly enjoyed the space. The home was clean, comfortable and exactly as described, with thoughtful details that made the stay feel very welcoming. The location was also very convenient and made it easy for us to get around. The host was very responsive throughout the entire process. A lovely experience and we would definitely recommend this place to others visiting the area:)"

Xinyi

$868 nightly

Dec 1 - Dec 2

Total with taxes and fees

11. Lakefront Cabin Pocono #2 / Leisure Lake Resort

Pocono Township

Darwin M.

$487 nightly

Nov 5 - Nov 6

Total with taxes and fees

12. Lakefront cabin #5 / Leisure Lake Resort

Pocono Township

Steven L.

$492 nightly

Nov 5 - Nov 6

Total with taxes and fees

13. Lakefront Cabin #4 / Fishing, Biking, Paddle Boats

Pocono Township

Krystelle W.

$487 nightly

Nov 5 - Nov 6

Total with taxes and fees

14. Lakefront Chalet Pocono #1 / 5 min Camelback Ski

Pocono Township

Dasaundra C.

$487 nightly

Nov 5 - Nov 6

Total with taxes and fees

A two-story house with a balcony, large windows, and a chimney.

15. Cozy Modern Camelback House

Tannersville

reyna b.

$712 nightly

Nov 5 - Nov 6

Total with taxes and fees

16. Romantic Couples Suite in the Poconos with Jetted Tub

Stroudsburg

$254 nightly

Nov 5 - Nov 6

Total with taxes and fees

A bathroom with a glass-enclosed shower, a sink with a marble countertop, and a toilet.

17. Romantic Couples Suite in the Poconos

Stroudsburg

$257 nightly

Nov 5 - Nov 6

Total with taxes and fees

18. Romantic Couples Suite in the Poconos

Stroudsburg

$245 nightly

Nov 8 - Nov 9

Total with taxes and fees

19. Romantic Couples Suite in the Poconos with Jetted Tub

Stroudsburg

$245 nightly

Nov 12 - Nov 13

Total with taxes and fees

20. Romantic Couples Suite in the Poconos

Stroudsburg

$257 nightly

Nov 5 - Nov 6

Total with taxes and fees

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Learn more about Portland

Explore attractions like Delaware River and Paulinskill River as you discover things to see and do in Portland.

See all hotels in Portland

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

Top reviews in Portland

A covered porch with rows of chairs and a view of a green house in the background.

Hotel Belvidere

Belvidere

10/10 Excellent

Richard

A large building with 'Penn Stroud' signage, street signs, and a 'No Turn on Red' sign.

The Penn Stroud, Stroudsburg - Poconos, an Ascend Collection Hotel

Stroudsburg

10/10 Excellent

John

A hotel entrance with a stone facade, a sign reading 'Hampton Inn & Suites,' and a tree in the foreground.

Hampton Inn & Suites Stroudsburg Pocono Mountains

Stroudsburg

10/10 Excellent

Judith

A Fairfield Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered walkway.

Fairfield Inn & Suites Stroudsburg Bartonsville / Poconos

Stroudsburg

10/10 Excellent

OLUWAGBENGA

A Holiday Inn Express & Suites hotel with a well-lit entrance and a clear signboard.

Holiday Inn Express & Suites Stroudsburg-Poconos by IHG

Stroudsburg

10/10 Excellent

Keith

A large, two-story house with a balcony, surrounded by trees.

Cherry Valley Manor Luxury Bed and Breakfast

Stroudsburg

10/10 Excellent

This was a WONDERFUL property. We normally don’t stay at B&Bs, but I have a medical condition that caused us to have to cancel our international travel for honeymoon and do something simple & not far away. The owners are from Ukraine and had two women from Ukraine who they took in to work there and get away from the war. They were ALL wonderful people. The breakfast was amazing and they even accommodated my gluten free and other dietary restrictions. They were genuine, lovely people and even the...

Steve

A hotel with a sign reading 'Staybridge Suites,' surrounded by trees and a parking lot.

Staybridge Suites East Stroudsburg - Poconos by IHG

East Stroudsburg

10/10 Excellent

Diane

A hotel with a flat facade, multiple windows, and a sign indicating it is a Hampton Inn.

Hampton Inn Easton

Easton

10/10 Excellent

JASON

A two-story house with a front porch, a brick facade, and a small garden area with shrubs and a tree.

The Lafayette Inn

Easton

10/10 Excellent

Barbara

A Baymont Inn & Suites building with a covered entrance, large windows, and a clear sky.

Baymont by Wyndham Bartonsville Poconos

Bartonsville

10/10 Excellent

Ronny

A modern hotel with a blue and white facade, a covered entrance, and a parking lot.

SpringHill Suites® by Marriott® Easton Bethlehem

Easton

10/10 Excellent

Craig

A covered patio with a table and chairs, white railings, and a view of a grassy yard and a house.

Woodfield Manor, A Sundance Vacations Property

Mount Pocono

10/10 Excellent

Really enjoyed my stay at Woodfield Manor, The staff is helpful and friendly, the check in process was a breeze..the grounds are beautiful! Its close to pretty much everything thats worth exploring/engaging in the Poconos Mountains. My cabin was very clean and cozy, perfect size , the fireplace kept our room so toasty, the bed was super comfy ! An overall very peaceful and pleasant stay and I will definitely return

Jennifer

Portland Chalets

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Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Portland chalets

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

2. NEW! Crestwood Hideaway - Hot Tub, Dog-Friendly, Walk to Lake, EV Charger

3. Award-Winning A-Frame | Hot Tub | Lakes | Firepit

4. Chalet Near Camelback, Ski, Game Room, Hot Tub, Fire Pits, Hiking, Pet, Karaoke!

5. Hot Tub | Cold Plunge | Sauna | Firepit

6. Hot tub/Cold Plunge/Sauna/Pools/Lakes

7. Japanese Soaking Tub | Hot Tub | Lakes | Sleeps 7

8. Pocono Sleep 16 Sauna Hot Tub + Private Acre + AC + King + Bunk Beds + Spa Bath

9. Romantic Couples Suite in the Poconos with Jetted Tub

10. 5BR Spa Chalet - Hot Tub, Pool Table, Loft

11. Lakefront Cabin Pocono #2 / Leisure Lake Resort

12. Lakefront cabin #5 / Leisure Lake Resort

13. Lakefront Cabin #4 / Fishing, Biking, Paddle Boats

14. Lakefront Chalet Pocono #1 / 5 min Camelback Ski

15. Cozy Modern Camelback House

16. Romantic Couples Suite in the Poconos with Jetted Tub

17. Romantic Couples Suite in the Poconos

18. Romantic Couples Suite in the Poconos

19. Romantic Couples Suite in the Poconos with Jetted Tub

20. Romantic Couples Suite in the Poconos

Learn more about Portland

Top reviews in Portland

Hotel Belvidere

10/10 Excellent

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