Deals on vacations and trips to Portland

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Portland flight + hotel vacation packages

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Cleveland Residences Chelsea

Cleveland Residences Chelsea

2 out of 5
London City Centre
Price was $1,560, price is now $1,175 per person
$1,175
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
This aparthotel features free WiFi in public areas, luggage storage, and laundry facilities. A virtual front desk are provided for your convenience.
1 Hotel Mayfair

1 Hotel Mayfair

5 out of 5
London City Centre
Save 100% on your flight
Price was $3,325, price is now $2,379 per person
$2,379
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
This hotel features 2 coffee shops/cafes and a gym. Enjoy the in-room fitness and perks like free WiFi. A restaurant and a bar/lounge offer onsite options for dining and drinks, and concierge services are provided.
Portobello Rd - North Ken by Viridian Apartments

Portobello Rd - North Ken by Viridian Apartments

4 out of 5
Notting Hill
Save 100% on your flight
Price was $2,000, price is now $1,486 per person
$1,486
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
Free WiFi in public areas is available at this apartment.
Chapter Spitalfields

Chapter Spitalfields

2 out of 5
London City Centre
Price was $1,860, price is now $1,387 per person
$1,387
per person
Feb 13 - Feb 19
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)
Free WiFi in public areas, a communal living room, and luggage storage are available at this apartment. Laundry facilities and concierge services are also provided.
The Fulham Penthouse

The Fulham Penthouse

3.5 out of 5
Hammersmith and Fulham
Save 100% on your flight
Price was $2,172, price is now $1,633 per person
$1,633
per person
Feb 13 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to London (LHR)

Top Portland hotels deals

Heights Hotel

Heights Hotel

3 out of 5
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.
The Aqua

The Aqua

3 out of 5
Castletown Portland England
$142 nightly
The price is $171 total per night
$171 total
Jan 5 - Jan 6, 2026
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.
Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

3 out of 5
12-18 Dorchester Road Weymouth England
Free Cancellation
Reserve now, pay when you stay
$91 nightly
The price is $109 total per night
$109 total
Jan 8 - Jan 9, 2026
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.
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade Weymouth England
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $84 total per night
$84 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
This hotel features a bar/lounge, free WiFi in public areas, and luggage storage.
The Duchess of Cornwall Inn

The Duchess of Cornwall Inn

3.5 out of 5
12 Queen Mother Square, Dorchester England
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $87 total per night
$87 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace is also provided.
Durdle Door Hotel

Durdle Door Hotel

3 out of 5
West Lulworth House, Main Road Wareham England
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $117 total per night
$117 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Luggage storage is 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

Portland Bill Lighthouse is a functioning lighthouse at Portland Bill, on the Isle of Portland, Dorset, England. One of the many beautiful places to see around the Jurassic Coast, down south in England. #jurassicCoast #PortlandBill #lighthouse #trulyBritish

Portland Bill Lighthouse

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

Portland Bill Lighthouse
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 Portland. Stroll along the area's waterfront, or simply savor its lively bars.

Portland Bill
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 Portland? While you're here, you can savor the top-notch restaurants.

Church Ope Cove

Frequently asked questions

How much are vacation packages to Portland?
Vacation packages, which include flights and hotels in Portland, start at just $1,175. 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.

Photos of local treasures

Browse Portland vacation photos for more inspiration

Portland
Photo by Doug Smith
Photo by Doug Smith
Photo by Leila Mae
Photo by Leila Mae
Photo by Doug Smith
Photo by Doug Smith
Photo by Chaz Selwyn
Photo by Chaz Selwyn