Portland Holiday Rentals

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Our top choices for Portland holiday rentals

9.6 out of 10, Exceptional, (95)
"My wife loved it…she has a rough week with work and just life in general, so I wanted to do something nice for her and surprised her with a stay here…she was really happy and loved everything about it…can’t wait to do this again 😊"
United States
Keven
The price is NZ$313
includes taxes & fees
4 Jan - 5 Jan 2026
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
10.0 out of 10, Exceptional, (6)
"Place is nice would stay again "
United States
nic
The price is NZ$635
includes taxes & fees
6 Jan - 7 Jan 2026
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Apartment in West Hartford

The Blue Back Bungalow
2.0 star property
9.4 out of 10, Exceptional, (18)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
The price is NZ$535
includes taxes & fees
30 Dec - 31 Dec
The Blue Back Bungalow

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is NZ$418
includes taxes & fees
9 Jan - 10 Jan 2026
The Historic Hideaway
8.6 out of 10, Excellent, (24)
"Great stay"
United States
Josh H.
The price is NZ$261
includes taxes & fees
28 Dec - 29 Dec
Lux Boutique Large Private LOFT Pratt St Hartford
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is NZ$485
includes taxes & fees
28 Dec - 29 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.8 out of 10, Exceptional, (34)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is NZ$468
includes taxes & fees
5 Jan - 6 Jan 2026
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
2.0 star property
The price is NZ$186
includes taxes & fees
6 Jan - 7 Jan 2026
Entire guest suite in South Windsor, Connecticut
10.0 out of 10, Exceptional, (1)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is NZ$847
includes taxes & fees
6 Jan - 7 Jan 2026
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (5)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is NZ$489
includes taxes & fees
4 Jan - 5 Jan 2026
Modern & Cozy Cape | 4 Bedroom House | Central Location
8.8 out of 10, Excellent, (48)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
The price is NZ$480
includes taxes & fees
6 Jan - 7 Jan 2026
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is NZ$271
includes taxes & fees
1 Jan - 2 Jan 2026
Humble Abode #2
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is NZ$360
includes taxes & fees
5 Jan - 6 Jan 2026
Central Chic Pad - with Free Parking, Heat & AC
7.6 out of 10, Good, (7)
" Not bad for the price "
United States
Audrey L.
The price is NZ$637
includes taxes & fees
28 Dec - 29 Dec
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is NZ$549
includes taxes & fees
5 Jan - 6 Jan 2026
Soothing 2-bedroom lower-level apartment in Berlin
9.6 out of 10, Exceptional, (5)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
United States
Hoyt
The price is NZ$330
includes taxes & fees
28 Dec - 29 Dec
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
9.4 out of 10, Exceptional, (13)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is NZ$282
includes taxes & fees
31 Dec - 1 Jan 2026
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
7.0 out of 10, Good, (4)
"The photos made the property look better than it was. The space wasn’t as clean as I’d expect and it was not very well appointed. There were no hand towels, the microwave didn’t work, there was no ice or way to make ice. It just wasn’t what I expected. "
United States
Heather C.
The price is NZ$359
includes taxes & fees
29 Dec - 30 Dec
Hartford Cityscape|Bushnell Park|Downtown Skyline
The price is NZ$322
includes taxes & fees
28 Dec - 29 Dec
Modern Living: 1-BR Near XLCenter|ConventionCenter

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (19)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is NZ$401
includes taxes & fees
7 Jan - 8 Jan 2026
Family Stays: Middletown, CT
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.
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Top Portland Hotel Reviews

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, 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 NZ$261 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?

Private Apartment in Berlin: This holiday home rental outside of Portland is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.