Photo by Matthew Jay

Find Luxury Hotels in Portland, NY

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Portland Luxury Hotels

Top Portland Luxury Hotels

We don't have any properties that match your exact search

Recommended hotels in Portland

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Relax by the fire pit in a serene outdoor space with a water view.

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

10.0 out of 10, Exceptional, (32)
"Perfect cottage for a relaxing weekend! We stayed to be super close to Fredonia and it was perfect! The cottage had everything we needed of our girls night!"
The price is ￥31,992
￥54,643 total
includes taxes & fees
Jul 17 - Jul 18
The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
BUTLER HOUSE at The Cherry Creek Inn
Sit beneath the pergola and take in the serene views of the expansive landscape.

BUTLER HOUSE at The Cherry Creek Inn

2.5 star property
7.4 out of 10, Good, (6)
"Do NOT book a room. The hotel is closed. We booked a room, drove all the way there and it was closed for renovations!!!"
BUTLER HOUSE at The Cherry Creek Inn
Holiday Inn Express & Suites Jamestown by IHG
Indulge in a variety of international dishes at our buffet, featuring cheese omelets and sausages.

Holiday Inn Express & Suites Jamestown by IHG

2.5 star property
9.2 out of 10, Wonderful, (735)
"Great place to stay"
The price is ￥18,753
￥21,709 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express & Suites Jamestown by IHG
The Joy Of Life - Where it's all about You!
Enjoy a serene beach experience with a rocky shoreline and calm sea.

The Joy Of Life - Where it's all about You!

10.0 out of 10, Exceptional, (45)
"Stayed here for fishing trip. Nice place and Charlene is very helpful."
The price is ￥17,117
￥35,835 total
includes taxes & fees
Jul 14 - Jul 15
The Joy Of Life - Where it's all about You!
Heaven Sent - including you!
Enjoy meals in this dining area with a round table for four, surrounded by a classic wooden chair set and a large window offering a view of the lush garden.

Heaven Sent - including you!

9.8 out of 10, Exceptional, (10)
"This was a lovely, clean property in a very quiet area. The outdoor area was beautiful and inside we had everything we needed for a great weekend visit. I’d recommend this property to anyone looking for a comfortable place to stay."
The price is ￥17,117
￥36,335 total
includes taxes & fees
Jul 21 - Jul 22
Heaven Sent - including you!
The Refined Retreat
Relax in a stylish living space with a flat-screen TV, fireplace, and comfortable seating area.

The Refined Retreat

10.0 out of 10, Exceptional, (3)
"Cozy. beautiful home next to the lake on a quiet street. The host has thought of everything. Lots of extras! Host is very responsive and helpful. Will definitely book again."
The price is ￥17,692
￥45,148 total
includes taxes & fees
Aug 10 - Aug 11
The Refined Retreat
Chautauqua Harbor Hotel - Jamestown
Experience the hotel's elegant entrance, featuring a covered patio area and beautifully manicured grounds.

Chautauqua Harbor Hotel - Jamestown

3.5 star property
9.6 out of 10, Exceptional, (1005)
"Very peaceful location, very nice staff "
The price is ￥31,466
￥35,557 total
includes taxes & fees
Jul 27 - Jul 28
Chautauqua Harbor Hotel - Jamestown
Charming Lake Cottage + Private Dock!
Marina

Charming Lake Cottage + Private Dock!

The price is ￥41,796
￥78,550 total
includes taxes & fees
Jul 19 - Jul 20
Charming Lake Cottage + Private Dock!
Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!
Fridge, microwave, oven, stovetop

Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!

9.6 out of 10, Exceptional, (8)
"Great communication with the host and a good location that was quiet and relaxing."
The price is ￥25,800
￥52,477 total
includes taxes & fees
Jul 14 - Jul 15
Family & pet friendly home with yard - 5 minutes from Chautauqua Lake!
The Stable at Windmill Ridge Farm
Stroll down this charming hallway, lined with a rug and featuring a convenient counter.

The Stable at Windmill Ridge Farm

9.4 out of 10, Exceptional, (13)
"Superb place "
The price is ￥18,429
￥34,985 total
includes taxes & fees
Aug 4 - Aug 5
The Stable at Windmill Ridge Farm
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.

Frequently asked questions

Are you looking for a luxury hotel for your stay in Portland?
Use Expedia to arrange your flight to Jamestown, NY (JHW-Chautauqua County) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want a posh hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Portland has to offer. Portland has some interesting things to see and do including Lake Erie and 21 Brix Winery, so you might want to take in the local sights during your visit.
When can I expect good weather in Portland?
Planning for the weather is an important factor for making your trip to Portland a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are February and January with an average of 30°F. The snowiest months in Portland are January, November, March, and February, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Portland?
When you're in Portland, enjoy exploring the sights and attractions here including Lake Erie, 21 Brix Winery, and Lily Dale Spiritual Center. If you have spare time during your trip, you might want to make a stop at Point Gratiot Park and Dunkirk Lighthouse and Veterans Park Museum.