Portland Vacations 2026

Top Portland hotels deals

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Portland NY

CA $283

CA $499 total

May 4 - May 5

includes taxes & fees

Stay at this cottage in Portland. Enjoy free WiFi, laundry facilities, and patios. Popular attractions 21 Brix Winery and Vetter Vineyards Winery are located nearby.

Kitchen

Washer

Chautauqua Harbor Hotel - Jamestown

10 Dunham Ave Celoron NY

Free cancellation

Reserve now, pay when you stay

CA $208

CA $235 total

May 11 - May 12

includes taxes & fees

Book a stay at this business-friendly hotel in Celoron. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lucille Ball Memorial Park and Northwest Arena are located nearby.

Pool

Parking included

Webb's Year Round Resort

125 W Lake Rd Mayville NY

Free cancellation

Reserve now, pay when you stay

CA $100

CA $113 total

May 28 - May 29

includes taxes & fees

Stay at this motel in Mayville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chautauqua Belle Steamboat and Chautauqua Bookstore are located nearby.

Pool

Hot tub

The White Inn

52 E Main Rd Fredonia NY

Free cancellation

Reserve now, pay when you stay

CA $192

CA $217 total

May 4 - May 5

includes taxes & fees

Stay at this hotel in Fredonia. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Darwin R. Barker Historical Museum and Fredonia Opera House are located nearby.

Breakfast included

Parking included

Holiday Inn Express & Suites Jamestown by IHG

2811 North Main Street Jamestown NY

Free cancellation

CA $144

CA $162 total

May 10 - May 11

includes taxes & fees

Book a stay at this business-friendly hotel in Jamestown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Roger Tory Peterson Institute and Russell E. Diethrick, Jr. Park are located nearby.

Pool

Breakfast included

Clarion Hotel Conference Center on Lake Erie

30 Lake Shore Dr E Dunkirk NY

Free cancellation

CA $160

CA $181 total

May 6 - May 7

includes taxes & fees

Book a stay at this business-friendly hotel in Dunkirk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chadwick Bay and Dunkirk Historical Museum are located nearby.

Breakfast included

Parking included

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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.

Popular places to visit

21 Brix Winery

You can enjoy a tasting or tour at 21 Brix Winery during your travels to Portland.

Portland Vacations

Get your escape off to an amazing start by familiarizing yourself with Portland before you head off.

Portland is located 10 miles (16 kilometers) southwest of Dunkirk. You'll also find it 25 miles (40 kilometers) northwest of Jamestown.

Places to visit in Portland

Whether you're a bit of a wine connoisseur or just can't resist the occasional glass, an afternoon at Vetter Vineyards Winery is sure to educate and entertain. Still need more ideas? It doesn't matter whether you're aiming for a hole-in-one or simply in the mood to brush up on your technique, you'll have a blast at Hillview Golf Course.

Where do you fly into for Portland?

Seats in the upright position, stow your tray tables and prepare to experience Portland! Once you hit the tarmac at Erie International Airport (ERI), the buzzing main streets will be just 40 miles (64 kilometers) northeast from here.

Frequently asked questions

How much are vacation packages to Portland?

Your travel fantasies can all come true in Portland for only . Package deals include flights and hotels, and they'll make your booking a piece of cake. All you'll have to worry about is getting out there and having a great time.

Where can I get the best vacation package deals for Portland?

Find your dream escape at Travelocity. With access to 400 airlines and 1,000,000 properties around the world, creating the ultimate Portland package deal couldn't be simpler.

Why should I book my Portland vacation bundle via Travelocity?

From our 24/7 customer support to our range of amazing destinations, we are dedicated to fulfilling your travel dreams. All you need to do is to click and book — our Price Match Guarantee will ensure you lock in the cheapest price.

Can I save on my Portland car rental if I bundle it with a hotel or flight?

With a Portland vacation package, you can bundle your flight, car and hotel bookings and save some serious money. If you're in the mood to see the best of this fantastic location, why not make tracks to CN Tower? This top attraction is 137 kilometers from Portland. With your own set of wheels, you'll be there soon enough.

Which airport is best for Portland?

Many people choose to fly into Buffalo Niagara Intl. Airport (BUF), 88 kilometers northeast of downtown Portland. Others prefer Erie Intl. Airport (ERI) (64 kilometers away from central Portland) or John C. Munro Hamilton Intl. Airport (YHM) (97 kilometers away from central Portland).

Where should I stay when visiting Portland?

The The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country is popular with many visitors. Book as soon as possible to avoid missing out.