Deals on vacations and trips to Portland

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Portland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Billings (BIL) 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.
The Spencer Hotel & Spa

The Spencer Hotel & Spa

2.5 out of 5
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Billings (BIL) to Jamestown (JHW)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free cooked-to-order breakfast each morning. A business center, a terrace, and a garden are also on offer.
Athenaeum Hotel

Athenaeum Hotel

3.5 out of 5
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Billings (BIL) to Jamestown (JHW)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a lobby fireplace, and luggage storage are also on offer.

Top Portland hotels deals

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

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

$316 nightly
The price is $357 total per night
$357 total
Sep 2 - Sep 3
Total includes taxes and fees
Stay at this cabin in Portland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions 21 Brix Winery and Vetter Vineyards Winery are located nearby.
Kitchen
Pet friendly
Clarion Hotel Conference Center on Lake Erie

Clarion Hotel Conference Center on Lake Erie

2.5 out of 5
30 Lake Shore Dr E, Dunkirk, NY
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $153 total per night
$153 total
Aug 17 - Aug 18
Total includes 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.
Breakfast included
Parking included
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave, Celoron, NY
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $162 total per night
$162 total
Sep 1 - Sep 2
Total includes taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Pool
Spa
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
125 W Lake Rd, Mayville, NY
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $136 total per night
$136 total
Sep 8 - Sep 9
Total includes 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.
Pool
Hot Tub
Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

Enjoy fall on the lake - colorful leaves, the grape harvest. Or, Winter snuggle.

$429 nightly
The price is $481 total per night
$481 total
Sep 7 - Sep 8
Total includes taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Grapevine Inn

Grapevine Inn

2.5 out of 5
12264 E Main Rd, North East, PA
$50 nightly
The price is $56 total per night
$56 total
Sep 1 - Sep 2
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Pet friendly
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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.

21 Brix Winery

Frequently asked questions

How much are vacation packages to Portland?
Your travel fantasies can all come true in Portland for only $1,295. 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.

Photos of local treasures

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Photo by Matthew Jay
Photo by Matthew Jay