Portland Holiday Rentals from €135: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Portland has to offer?

Tranquil Waters: Modern Bolton Escape on the Lake : This holiday home rental outside of Portland is located on the waterfront, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Our top choices for Portland holiday rentals

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Gabrielly

includes taxes & fees

11 Jun - 12 Jun

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Coventry Lake

Jamie S.

includes taxes & fees

4 Jun - 5 Jun

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Coventry Lake

Christine M.

includes taxes & fees

4 Jun - 5 Jun

2BR Apartment Near Wesleyan 102

Washington Street Historic District

includes taxes & fees

4 Jun - 5 Jun

Humble Abode #2

Manchester Center

Jonathan

includes taxes & fees

10 Jun - 11 Jun

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Lake Pocotopaug

Jennifer J.

includes taxes & fees

22 Jun - 23 Jun

Entire guest suite in South Windsor, Connecticut

South Windsor

Jan E.

includes taxes & fees

7 Jun - 8 Jun

Walk To Goodspeed Opera House!

East Haddam

Annette L.

includes taxes & fees

8 Jun - 9 Jun

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Top Portland Hotel Reviews

The Capitol Hotel

2/10 Terrible

"Convenient location, place was all right in side. Needs updates, like being in a horror film."

Ramada by Wyndham Hartford North / Bradley Airport

4/10 Poor

"The front office lady was definitely not suited to front office work, had no customer service mindset. We were there just for a night, and had to leave at 3 am to catch a flight from Bradley airport. I had only one request, that the room be as close to the main entrance as possible. She finally gives the room key and we set out - literally it was at the very far end (it is a large U shaped structure). If she would have told us that she could not accommodate our request, it would have been alright, but she was smug about it. When I called her from the room, she was not polite as if it is our fault for picking a king bed room:) The room had a weird smell, the bathroom sink was cracked, there was a cleaning note that everything is sanitized etc., and someone had written "ALL LIES" on it lol:) The bathroom door lock was not working. The property has potential, it is close to a large airport just a well maintained room, basic cleanliness and a good hospitable front desk will go a long way."

Marriott Hartford/Windsor Airport

6/10 Okay

"Only think l have with this hotel is no continental breakfast and the breakfast that we did order. It was cold and didn't have The Economist with it. The coffee maker didn't work. Overall, the stay was nice. And I was comfortable, and there was no microwave, which I would think that should be one of the amenities that they have in the room. In case if you don't want to go out, you want to warm up your food inside instead of going all the way downstairs to the 1st floor to warm up your food. That part didn't make sense to me."

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as €135 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Portland?

Yes, there are holiday rentals in Portland close to Brownstone Exploration & Discovery Park, or you can select a more secluded option if you're looking for a relaxing stay. Portland is known for its riverfront and wineries. Make sure you have time to check out the theme park and restaurants during your trip.

What are some of the best holiday rentals that Portland has to offer?

Tranquil Waters: Modern Bolton Escape on the Lake: This holiday home rental outside of Portland is located on the waterfront, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Portland?

Family-friendly attractions include Brownstone Exploration & Discovery Park, whereas Connecticut River is a spot to enjoy the outdoors. Arrigoni Winery and Chris Cote's Toptracer Golf Range and Performance Center are other places to visit while you're in town.

What’s a holiday rental in Portland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Portland. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.

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Check prices for these dates

Our top choices for Portland holiday rentals

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks