Portland Vacation Packages 2026 from $958

Portland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Webb's Year Round Resort

$958

per person

Jul 27 - Jul 31

found 24 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Jamestown (JHW)

This motel features an indoor pool and a hot tub. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A lobby fireplace, a computer station, and laundry facilities are also on offer.

3640 Wells Bay Road 3 Bedroom Home by RedAwning

$2,197

per person

Jul 27 - Jul 31

found 24 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Jamestown (JHW)

This vacation home features barbecue grills.

Top Portland hotels deals

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

Portland NY

$323 nightly

$365 total

May 20 - May 21

Total with taxes and fees

This cottage features laundry facilities.

Secluded Lake Erie Escape with 550 Ft of Lake View Frontage on 7.5 Private Acres

Portland NY

Get rates

Stay at this vacation home in Portland. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Lake Erie State Park and 21 Brix Winery are located nearby.

Chautauqua Harbor Hotel - Jamestown

10 Dunham Ave Celoron NY

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$172 total

May 25 - May 26

Total with taxes and fees

The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy a meal from the a restaurant and perks like free self parking.

Webb's Year Round Resort

125 W Lake Rd Mayville NY

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$89 total

May 20 - May 21

Total with taxes and fees

This motel features an indoor pool and a hot tub. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A lobby fireplace, a computer station, and laundry facilities are also on offer.

Clarion Hotel Conference Center on Lake Erie

30 Lake Shore Dr E Dunkirk NY

Free Cancellation

$126 nightly

$142 total

Jun 7 - Jun 8

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Best Western Dunkirk & Fredonia Inn

3912 Vineyard Drive Dunkirk NY

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

May 20 - May 21

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an indoor pool on site, and a 24-hour front desk and express check-out are also provided.

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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.

Frequently asked questions

How much are vacation packages to Portland?

Your travel fantasies can all come true in Portland for only $958. 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 85 mi 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), 55 mi northeast of downtown Portland. Others prefer Erie Intl. Airport (ERI) (40 mi away from central Portland) or John C. Munro Hamilton Intl. Airport (YHM) (60 mi 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.