Portland Vacation Packages 2025/2026 from $989

Portland flight + hotel vacation packages

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

Charles Hope London Battersea

Wandsworth

$989

per person

Nov 27 - Nov 30

found 1 day ago

Roundtrip flight included

New York (JFK) to London (LHR)

A 24-hour gym is featured at this apartment, along with free WiFi in public areas and concierge services. A virtual front desk are provided for your convenience.

The Beaumont Mayfair

London City Centre

Save 100% on your flight

$2,340

per person

Nov 21 - Nov 25

found 16 hours ago

Roundtrip non-stop flight included

Boston (BOS) to London (LHR)

A full-service spa, 2 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.

Treehouse Hotel London

London City Centre

Save 100% on your flight

$1,550

per person

Nov 7 - Nov 12

found 2 days ago

Roundtrip non-stop flight included

Boston (BOS) to London (LHR)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A terrace, a snack bar/deli, and dry cleaning are also on offer.

Forset Court Residences

London City Centre

Save 100% on your flight

$1,213

per person

Nov 15 - Nov 21

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to London (LHR)

This apartment includes free WiFi in public areas and a virtual front desk.

Leicester House Hotel

London City Centre

Save 100% on your flight

$1,495

per person

Nov 7 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to London (LHR)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Luggage storage and a safe deposit box are also provided.

Top Portland hotels deals

Heights Hotel

Yeates Road, Portland, England

Get rates

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

Breakfast included

Parking included

The Aqua

Castletown, Portland, England

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$171 total

Oct 7 - Oct 8

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like English breakfast and WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Breakfast included

Free WiFi

Fairhaven Hotel

Fairhaven Hotel, 37 Esplanade, Weymouth, England

Free Cancellation

Reserve now, pay when you stay

$66 nightly

$80 total

Nov 5 - Nov 6

Total with taxes and fees

This hotel features a bar/lounge, free WiFi in public areas, and luggage storage.

Free WiFi

Breakfast available

Durdle Door Hotel

West Lulworth House, Main Road, West Lulworth, Wareham, England

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$116 total

Nov 2 - Nov 3

Total with taxes and fees

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

Pet friendly

Free WiFi

Best Western Weymouth Hotel Rembrandt

12-18 Dorchester Road, Weymouth, England

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$144 total

Oct 12 - Oct 13

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy the indoor pool and perks like free self parking.

Pool

Hot Tub

Alexandra Hotel

27-28 The Esplanade, Weymouth, England

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$89 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features a bar/lounge, a coffee shop, and free WiFi in public areas. A terrace, a communal living room, and luggage storage are also on offer.

Free WiFi

Breakfast available

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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

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 lively bars.

Head down to see the lighthouse and pulpit rock

Portland Bill

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 charming coffeehouses.

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 $989. 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.