Portland Vacation Packages 2025 from $2,493

Portland flight + hotel vacation packages

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

Apex City of Bath Hotel

Bath City Centre

per person

Aug 3 - Aug 6

found 17 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to London (LHR)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. You'll appreciate the sauna, bar/lounge, and concierge services.

Bailbrook House

per person

Aug 3 - Aug 6

found 17 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to London (LHR)

This smoke-free hotel features 2 restaurants, a bar/lounge, and a gym. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Free self parking, a garden, and a picnic area are also offered.

Prince of Burford

per person

Aug 3 - Aug 6

found 17 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to London (LHR)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a picnic area are also on offer.

The Royal Crescent Hotel & Spa

Upper Town

per person

Aug 3 - Aug 6

found 17 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to London (LHR)

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference space. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

No.15 by GuestHouse, Bath

Bathwick

per person

Aug 3 - Aug 6

found 17 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to London (LHR)

A bar/lounge and a 24-hour front desk are featured at this hotel, along with self parking. WiFi in public areas is free. A garden, a snack bar/deli, and express check-out are also on offer.

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Free WiFi in public areas and luggage storage are available at this hotel.

Pet friendly

Free WiFi

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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

Portland Bill Lighthouse

5/5(4 reviews)

Find out about the history of Southwell when you spend time at Portland Bill Lighthouse. Wander the area's beautiful beaches or simply enjoy one of its charming coffeehouses.

Head down to see the lighthouse and pulpit rock

Portland Bill

5/5(1 review)

Commune with nature and explore the great outdoors at Portland Bill during your travels in Southwell. Stroll along the area's beautiful beaches, or simply savor its lively bars.

Beautiful quiet beach
Very big pebbles, rocks so probably don't attempt to go barefoot.

Church Ope Cove

Why not spend a carefree afternoon at Church Ope Cove during your travels in Southwell? Amble around the area's seaside or visit its spas.

Frequently asked questions

How much are vacation packages to Portland?

Vacation packages, which include flights and hotels in Portland, start at just $2,493. Turn your daydreams into reality and book your dream trip with Travelocity today.

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

Travelocity is here to help you snap up a Portland package deal. With no less than 400 air carriers and 1,000,000 properties around the world, we know you'll find one that works for you.

Why should I book my Portland vacation bundle via Travelocity?

From our 24/7 customer support to our range of exciting destinations, we are committed to fulfilling your vacation dreams. All you have to do is to click and book --- our Price Match Guarantee will ensure you get the lowest price.

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

Combining your car, hotel and flight into a Portland vacation package is an excellent way to score an amazing deal. Plus, having your own car rental gives you the freedom to make your way to all the landmarks you can't wait to check out. Located 120 mi from Portland, Big Ben is one place that should be on your itinerary. Put together a driving playlist and make a day trip of it.

Which airport is best for Portland?

Bristol Intl. Airport (BRS) is one of the best airports for Portland. It's around 60 mi north of the buzzing city center. Other choices include Southampton Airport (SOU) (55 mi away from central Portland) and Bournemouth Intl. Airport (BOH) (30 mi away from central Portland).

What is there to do in Portland?

Portland has plenty of things to see and do, such as Weymouth and Portland National Sailing Academy and Portland Castle. These two impressive attractions top most visitors' to-do lists.

Where should I stay when visiting Portland?

If you're looking for somewhere to spend your nights, consider the The Aqua. It's the top pick for many visitors.