Photo by Rick Bucchino

Portland Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Holiday Rentals in Portland

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (70)
"Great stay"
The price is S$258
includes taxes & fees
29 Sept - 30 Sept
Postcard Cabins Machimoodus
10 Mi to Hartford: Family Home w/ Yard
Interior

10 Mi to Hartford: Family Home w/ Yard

3.0 star property
10 Mi to Hartford: Family Home w/ Yard
Charming Windsor Home w/ Private Backyard!
Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Very nice and spacious room, clean and well maintained"
Christopher 1-night trip
Posted 3 days ago
The Capitol Hotel

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’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.