Downtown Portland Vacation Packages 2025/2026 from $550

Downtown Portland flight + hotel vacation packages

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

The McKernan Inn

Save 100% on your flight

per person

Sep 21 - Sep 24

found 2 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Portland (PWM)

This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.

Nautical Mile

Save 100% on your flight

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Portland (PWM)

A seasonal outdoor pool is featured at this aparthotel, along with free self parking. A picnic area and a computer station are also provided.

Admiral Peary Inn

per person

Aug 1 - Aug 8

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A coffee shop, a garden, and a snack bar/deli are also on offer.

Portland Harbor Hotel

Downtown Portland

Save 100% on your flight

per person

Aug 13 - Aug 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Portland (PWM)

This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

Chebeague Island Inn

per person

Sep 14 - Sep 18

found 7 hours ago

Roundtrip flight included

Dallas (DFW) to Portland (PWM)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate perks like free WiFi and a free ferry terminal shuttle. A garden, a lobby fireplace, and a picnic area are also on offer.

Top Downtown Portland hotels deals

Hyatt Place Portland Downtown - Old Port Square

433 Fore St, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

Free airport shuttle

Pet friendly

Portland Regency Hotel & Spa

20 Milk Street, Portland, ME

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A full-service spa, a hot tub, and a restaurant are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a roundtrip airport shuttle. There's a gym on site, and laundry facilities and concierge services are also offered.

Canopy by Hilton Portland Waterfront

9 Center Street, Portland, ME

Free Cancellation

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This hotel features 2 restaurants and a 24-hour gym. WiFi in public areas is free. Valet parking, a lobby fireplace, and a communal living room are also offered.

Pet friendly

Free WiFi

Portland Harbor Hotel

468 Fore Street, Portland, ME

Free Cancellation

Reserve now, pay when you stay

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This hotel features 3 coffee shops/cafes and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll find a restaurant and a bar/lounge onsite for dining and drinks, along with a 24-hour front desk.

Hilton Garden Inn Portland Downtown Waterfront

65 Commercial St, Portland, ME

Free Cancellation

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This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and laundry facilities.

Pool

Hot Tub

Holiday Inn Portland-By the Bay by IHG

88 Spring St, Portland, ME

Free Cancellation

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This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like a free area shuttle.

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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

State Theatre

4.5/5(88 reviews)

You can make plans for a show at State Theatre during your trip to Portland. Experience the area's entertainment choices and great live music.

Portland Museum of Art

4.5/5(255 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

MECA - Portland - building previously Porteous, Mitchell and Braun department store

Maine College of Art

5/5(1 review)

You can spend an afternoon browsing the exhibits at Maine College of Art during your trip to Portland. Experience the area's acclaimed theater scene and great live music.

Frequently asked questions

How much are vacation packages to Downtown Portland?

Packages, which provide both flights and hotels in Downtown Portland, are priced from as little as $550. Turn your daydreams into reality and begin your booking with Travelocity today.

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

You can grab amazing Downtown Portland package deals with Travelocity. Select from 400 air carriers and 1,000,000 worldwide properties and turn those travel dreams into reality.

Why should I book my Downtown Portland vacation bundle via Travelocity?

You'll not only enjoy great savings, but you can also access our round-the-clock support, quality service and a Price Match Guarantee. Journey across the world, uncover hidden sights and forge unforgettable memories --- we'll take care of the important details.

Will I save money on my Downtown Portland car rental if I book it with a hotel or flight?

You sure can --- and booking one of our Downtown Portland vacation packages is the best way to do this. Bundle any combination of a hotel, car, flight and experience and score awesome discounts. The more you book, the more you save. There are loads of top attractions in and around Downtown Portland to put on your bucket list, including Fenway Park (100 mi from Downtown Portland). Nothing tops exploring places like this with the freedom of your own wheels.

What is there to do in Downtown Portland?

Grab your vacation itinerary and make a note of Portland Museum of Art and Wadsworth-Longfellow House. They're two of the top attractions in Downtown Portland.