Portland Holidays from £419

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages 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.
Best Western Manchester

Best Western Manchester

2.5 out of 5
Price was £470, price is now £419 per person
£419
per person
26 Aug - 29 Aug
found 1 day ago
Return direct flight included
George Town (GCM) to Hartford (BDL)
8.6/10 Excellent! (634 reviews)
Clean and bright. Breakfast was great!

Reviewed on 30 Jun 2026

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was £818, price is now £645 per person
£645
per person
26 Aug - 29 Aug
found 1 day ago
Return direct flight included
George Town (GCM) to Hartford (BDL)
9.8/10 Exceptional! (1,001 reviews)
Loved how clean the hotel was. The AC and fresh quality of the room. Staff very friendly. The restaurant lowered the quality tremendously. It didn’t match. Although breakfast was included the quality was watered down. Same buffet every morning. Taste was lower grade. Presentation looks good but the experience felt like a pub. No menu was offered as a substitute. Seating was not classy. Or comfy. I wasn’t informed of other options in the hotel. But outside from the restaurant it’s pleasant.

Reviewed on 6 Jul 2026

Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
Price was £691, price is now £615 per person
£615
per person
19 Aug - 22 Aug
found 1 day ago
Return direct flight included
George Town (GCM) to Hartford (BDL)
8.4/10 Very good! (1,010 reviews)
2nd summer staying here and we love it!

Reviewed on 8 Jul 2026

Motel 6 Enfield, CT - Hartford

Motel 6 Enfield, CT - Hartford

2 out of 5
Price was £509, price is now £463 per person
£463
per person
19 Aug - 22 Aug
found 1 day ago
Return direct flight included
George Town (GCM) to Hartford (BDL)
6.8/10 (1,009 reviews)
Clean room bed was very comfortable

Reviewed on 7 Jul 2026

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was £611, price is now £558 per person
£558
per person
19 Aug - 22 Aug
found 1 day ago
Return direct flight included
George Town (GCM) to Hartford (BDL)
8.8/10 Excellent! (1,002 reviews)
Walking into the Hilton Garden the lobby was so nice and clean. The front desk attendant was very friendly. The rooms were spacious, beds comfortable and overall a great place to stay

Reviewed on 6 Jul 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

Solano Inn

2.5 out of 5
1503 Portland-Cobalt Rd Portland CT
Fully refundableReserve now, pay when you stay
The price is £100 per night from 19 Jul to 20 Jul
£100
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (250 reviews)
"The room clean and decorated in away that was comfortable and eye appealing. The remote for the TV was a little touchy. They had wine glasses and glass drinking glasses in the cupboard by the coffee maker and mini fridge . That was an unexpected positive"

Reviewed on 7 Jul 2026

Solano Inn
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Fully refundableReserve now, pay when you stay
The price is £66 per night from 20 Jul to 21 Jul
£66
20 Jul - 21 Jul
includes taxes & fees
7/10 Good! (1,212 reviews)
"Book for double twin. Was told since we checked in later in the night the room was given away. Room smelled moldy and the gap in the door at the bottom was at least 1/2 inch. Big enough for any bugs or small vermin to get through. Would not stay there again. Checked out as soon as I woke up and ..."

Reviewed on 7 Jul 2026

Motel 6 Wethersfield, CT - Hartford
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd Hartford CT
Fully refundableReserve now, pay when you stay
The price is £88 per night from 4 Aug to 5 Aug
£88
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (1,092 reviews)
"Nice clean place to stay for business travel"

Reviewed on 8 Jul 2026

Best Western Hartford Hotel & Suites
See all 726 properties in Portland
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.
See properties

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 £419. 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.

Explore a world of travel with Expedia

* 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.