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Portland Holiday Rentals

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Holiday Rentals in Portland

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (70)
"Great stay"
The price is NZ$347
includes taxes & fees
29 Sept - 30 Sept
Postcard Cabins Machimoodus

Lux Boutique Large Private LOFT Pratt St Hartford

8.4 out of 10, Very good, (20)
"Location was great. Lots of things to do and many nearby options for eating and drinks. View was disappointing—dark and one window facing a brick wall. Biggest complaint was neighbors and noise—first two nights there was loud music and parties until early morning hours."
The price is NZ$354
includes taxes & fees
29 Sept - 30 Sept
Lux Boutique Large Private LOFT Pratt St Hartford

Cozy apartment in charming Hartford with AC, WiFi

10.0 out of 10, Exceptional, (3)
"All was as advertised. The Xfinity INDOOR theatre us across the the street. Xfinity OUTDOOR theatre/ arena is only about a .8 mile walk away. We took an UBER there and walked back after our concert"
The price is NZ$299
includes taxes & fees
12 Oct - 13 Oct
Cozy apartment in charming Hartford with AC, WiFi

Totally Private Cozy studio in awesome Hartford with WiFi, AC

9.2 out of 10, Wonderful, (10)
"Great!"
The price is NZ$291
includes taxes & fees
28 Sept - 29 Sept
Totally Private Cozy studio in awesome Hartford with WiFi, AC

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

10.0 out of 10, Exceptional, (46)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is NZ$1,210
includes taxes & fees
6 Oct - 7 Oct
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Cozy Safe Home

The price is NZ$562
includes taxes & fees
29 Sept - 30 Sept
Cozy Safe Home

Conference Room Rental no sleeping arrangements

The price is NZ$1,601
includes taxes & fees
28 Sept - 29 Sept
Conference Room Rental no sleeping arrangements

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (5)
The price is NZ$491
includes taxes & fees
28 Sept - 29 Sept
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

10.0 out of 10, Exceptional, (3)
"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."
The price is NZ$370
includes taxes & fees
16 Oct - 17 Oct
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

New Furnished Apt in West Hartford w/ Parking and Central AC

6.8 out of 10, (3)
"Good communication with the manager, quiet place and extremely clean. I enjoyed it"
The price is NZ$321
includes taxes & fees
1 Oct - 2 Oct
New Furnished Apt in West Hartford w/ Parking and Central AC

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (40)
"Comfortable with all the amenities you could need "
Cozy dog friendly updated house in quiet village adjacent to park

Fully Furnished Private Loft Style Charm Trumbull Elevator

7.0 out of 10, Good, (2)
"Great place to stay. Lots of room compared to a hotel room and it's nice to have the kitchen area. We used the bonus spaces a lot and found the building to be very quiet from room to room. The noise from outside at night was mostly car noise and seemed pretty standard for being in a central location. Thank you!"
The price is NZ$417
includes taxes & fees
29 Sept - 30 Sept
Fully Furnished Private Loft Style Charm Trumbull Elevator

Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

2.0 star property
9.4 out of 10, Exceptional, (12)
"Beautiful location, very comfortable for our small family."
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi

Experience Downtown Hartford near XL Center

6.8 out of 10, (5)
"The day I arrived the property wasn’t ready and I had to find a hotel near there. Needless to say it’s not near nice areas but that’s where the hotel was. They only told me after I didn’t get a code to get in and I had to contact them. Good news was that they reimbursed the hotel quickly. The unit is very clean but very minimal. The refrigerator has no freezer section and the kitchen only a range top, no oven. There’s also no coffee maker, iron or ironing board and laundry was done offsite. All...
The price is NZ$299
includes taxes & fees
19 Oct - 20 Oct
Experience Downtown Hartford near XL Center

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (19)
"I've stayed here multiple times and it was amazing as always. Great communication, clean, and beautiful! "
The price is NZ$1,619
includes taxes & fees
27 Sept - 28 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

9.4 out of 10, Exceptional, (8)
"Needed a place to sleep for a couple of nights and this worked for us."
The price is NZ$300
includes taxes & fees
29 Sept - 30 Sept
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

10.0 out of 10, Exceptional, (41)
"Lots of activities both inside and outside. The house is very well maintained and inviting. Thank you!"
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

10.0 out of 10, Exceptional, (4)
"Stay was wonderful! Everythjng was nice, tidy, and organized! Had just enough for what i needed! Will definitely stay again!"
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

Go Jump in the Lake!

10.0 out of 10, Exceptional, (144)
"owner was super nice and the environment was great i would come back "
Go Jump in the Lake!

New!Quaint & Convenient Hideaway: Great Location

9.6 out of 10, Exceptional, (14)
"Our family of 4 stayed there while visiting Hartford for our daughter’s college graduation. Great location great property and responsive host. Would def stay again!"
New!Quaint & Convenient Hideaway: Great Location
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

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$291 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?

New!Quaint & Convenient Hideaway: Great Location: This holiday home rental outside of Portland has air conditioning and a Smart TV to help you feel perfectly comfortable 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.