Portland Holidays from £745
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Portland Holiday
The eclectic style and cultural experiences are just the beginning of the things Portland has going for it. Discover the sights and sounds of this city the way you want with a personalised Portland holiday package. A trip to Portland is an ideal opportunity to do a bit of sightseeing. Check out renowned attractions like Wesleyan University, Brownstone Exploration & Discovery Park and TPC River Highlands. Expedia can help you escape the everyday. Tailor your holiday to Portland to suit your style of travel, whatever that may be!
Top Portland Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Motel 6 Enfield, CT - Hartford
£745
per person
29 Sept - 6 Oct
found 17 hours ago
Return direct flight included
Dublin (DUB) to Hartford (BDL)
7/10 Good! (1,040 reviews)
I really enjoyed the hotel. It was amazing at the price it cannot be beat. I ended up staying a night cause it was closest to Six Flags New England. Very clean. The windows just need a little dusting. But overall an amazing experience. Definitely recommend it 😃
Reviewed on 24 Aug 2026
Two Trees Inn
£946
per person
8 Oct - 13 Oct
found 1 day ago
Return direct flight included
London (LON) to Hartford (BDL)
8.6/10 Excellent! (252 reviews)
I was happy to see they had reopened. The staff was awsome. Housekeeping checked in on us anything we needed (coffee ,towels, trash emptied etc. during our stay just let them know.
Reviewed on 25 Aug 2026
Candlewood Suites Windsor Locks Bradley Arpt by IHG
£826
per person
29 Sept - 6 Oct
found 17 hours ago
Return direct flight included
Dublin (DUB) to Hartford (BDL)
8.4/10 Very good! (1,053 reviews)
Very quick trip, I literally stayed overnight for five hours. Ended up getting one of the suites and it was a very nice room especially considering what I paid. The lady who was working the overnight shift was also very lovely. She was super nice and helpful!
Reviewed on 25 Aug 2026
Portland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 5,900 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Brownstone Exploration & Discovery Park, Dinosaur State Park and Powder Ridge Mountain Park and Resort |
Top hotels in Portland
Solano Inn
1503 Portland-Cobalt Rd Portland CT
Fully refundableReserve now, pay when you stay
£69
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very good! (271 reviews)
"Very well-managed property."
Reviewed on 24 Aug 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
£80
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,431 reviews)
":p"
Reviewed on 25 Aug 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
£72
26 Aug - 27 Aug
includes taxes & fees
7.4/10 Good! (1,509 reviews)
"Everything was very good and easy."
Reviewed on 24 Aug 2026
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.
Stay near popular Portland attractions
Arrigoni Winery
8.8/10 (6 reviews)
This rustic Connecticut vineyard crafts over 30 speciality wines and unique ciders in a countryside setting. Savour tastings on the vineyard-side patio while enjoying live music and made-to-order food.
Chris Cote's Toptracer Golf Range and Performance Center
Elevate your golf game at this tech-forward range with Toptracer technology tracking every swing in real time. Practice in heated bays or schedule a professional fitting session for personalised improvement.
Frequently asked questions
How much does a Portland travel package cost?
We make it easy to see the world, with Portland travel packages starting from as low as £745. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your travel itinerary?
If I'm not able to travel, can I cancel my Portland travel package?
You can. We get that even the best-laid plans can go awry, so we're here to help if you have to make changes to your Portland travel package. It may be possible to cancel or amend your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if your booking was made more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Portland?
Browse and book everything in one place with our Portland travel packages. You'll discover deals on hotels, flights and more that'll keep your pocketbook happy and your adventurous spirit full. And, with more than 550 airlines and 1,000,000 hotels throughout the world to choose from, you have countless opportunities to mix and match as you want.
Does Expedia offer Book Now, Pay Later Portland holidays?
Expedia has partnered with online lender Klarna to make booking your next break easier on your budget. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Consider these flexible payment options:
- Pay monthly holidays: Klarna offers easy monthly payment plans that fit all budgets, so you can take that well-deserved holiday sooner.
- Pay in instalments holidays: If you'd like to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Hitting the "book now" button is easier with this payment option. Just put down a small deposit on your booking and then start working on your travel plans.
Where should I stay in Portland?
Stay close to the action. Many travellers book hotels within easy reach of popular sights, like Wesleyan University, Brownstone Exploration & Discovery Park and Kidcity Childrens Museum.
What are the top hotels in Portland?
Make a reservation at Hilton Stamford Hotel & Executive Meeting Centre. It's one of the neighbourhood's most popular hotels. Another highly rated option in Portland is Howard Johnson by Wyndham Mystic.
How far in advance should I book my Portland holiday?
Travellers are generally able to browse international airfares on Expedia up to a year in advance of departure. Booking late? With a little bit of luck, it's still possible to score a cheaper ticket only weeks before your flight.
What does an Expedia Portland travel package include?
Travel packages include rental cars, hotels and flights, but you can combine any of them to create your perfect Portland holiday. You can also add on fun things like experiences and activities once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll get access to deals you won't find anywhere else.
What should I know before booking a Portland travel package?
A package can be cheaper than individually booking everything you need for your adventure. For example, bundle your hotels, flights and rental cars and score impressive savings. Whatever type of holiday you have in mind, you'll find a package that's perfect for you.
Can I choose my airline with a Portland Expedia travel package?
With a travel package, you're in charge. Whether you want to fly to Portland in first class or coach, simply choose from the available airline options. Expedia has access to more than 550 partner airlines across the world.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
