Photo by Rick Bucchino

Holiday Rentals in Portland

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Portland

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (72)
"Very nice cabins "
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Totally Private Cozy studio in awesome Hartford with WiFi, AC
8.6 out of 10, Excellent, (11)
"Great!"
The price is €140
includes taxes & fees
15 Oct - 16 Oct
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
The price is €226
includes taxes & fees
21 Oct - 22 Oct
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Microwave
Cozy apartment in charming Hartford with AC, WiFi
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 €154
includes taxes & fees
15 Oct - 16 Oct
Cozy apartment in charming Hartford with AC, WiFi
Interior
Experience Downtown Hartford near XL Center
Experience Downtown Hartford near XL Center
6.0 out of 10, (6)
"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 €135
includes taxes & fees
27 Oct - 28 Oct
Experience Downtown Hartford near XL Center
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford
Lux Boutique Large Private LOFT Pratt St Hartford
8.4 out of 10, Very good, (21)
"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 €144
includes taxes & fees
15 Oct - 16 Oct
Lux Boutique Large Private LOFT Pratt St Hartford
Exterior
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (48)
"Amazing property, we loved everything about it, highly recommended, will stay again "
The price is €662
includes taxes & fees
3 Nov - 4 Nov
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Fridge, microwave, oven, stovetop
Private Apartment in Berlin
Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
The price is €289
includes taxes & fees
11 Nov - 12 Nov
Private Apartment in Berlin
Interior
Conference Room Rental no sleeping arrangements
Conference Room Rental no sleeping arrangements
The price is €812
includes taxes & fees
17 Oct - 18 Oct
Conference Room Rental no sleeping arrangements
3 bedrooms, iron/ironing board, WiFi, bed sheets
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
5.4 out of 10, (3)
"My son and I booked this property last minute. The owner was very quick to get back to us. It was very clean and had everything we needed. We would definitely stay there again."
The price is €247
includes taxes & fees
22 Oct - 23 Oct
3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
9.6 out of 10, Exceptional, (4)
"Cozy, clean, comfortable. Location is excellent and accessible to restaurants and venues. Highly recommended. "
The price is €178
includes taxes & fees
1 Nov - 2 Nov
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
TV
Stylish Downtown Business| Hospital | WD | GYM
Stylish Downtown Business| Hospital | WD | GYM
8.0 out of 10, Very good, (5)
"This apartment is in a great location, right by the park in the heart of downtown. The unit is very sparse and lacks general amenities. The apartment photos don’t reflect the decor of the unit. The couch was updated, decorative items shown in photos were missing, etc. If you stay here make sure to tell the hosts how many are in your party. We had to request extra linens, washcloths, towels. They were provided to us but I expect to have these items at a rental when I arrive. The location was...
The price is €226
includes taxes & fees
16 Oct - 17 Oct
Stylish Downtown Business| Hospital | WD | GYM
Private kitchen
Fully Furnished Private Loft Style Charm Trumbull Elevator
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 €170
includes taxes & fees
15 Oct - 16 Oct
Fully Furnished Private Loft Style Charm Trumbull Elevator
Property grounds
Humble Abode #2
Humble Abode #2
2.0 star property
The price is €117
includes taxes & fees
16 Oct - 17 Oct
Humble Abode #2
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
10.0 out of 10, Exceptional, (5)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
The price is €250
includes taxes & fees
15 Oct - 16 Oct
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Fridge, microwave, oven, stovetop
Modern Condo|DWNTN Hartord| XL Center| GYM
Modern Condo|DWNTN Hartord| XL Center| GYM
4.0 out of 10, (2)
"The location was fantastic.Check-In, Parking and Check-Out easy.The images of the condo were misleading.- cockroaches were present- Floors were not swept- sofa bed sheets were still on bed and unwashed- makeup on the pillow cases from the pullout couch and the hair dryer bag- bedside furniture had broken drawers- one kitchen chair was extremely wobbly- kitchen table light did not workWe will not staying here again."
The price is €205
includes taxes & fees
15 Oct - 16 Oct
Modern Condo|DWNTN Hartord| XL Center| GYM
Property grounds
Cozy dog friendly updated house in quiet village adjacent to park
Cozy dog friendly updated house in quiet village adjacent to park
10.0 out of 10, Exceptional, (41)
"Very nice stay! Yard is beautiful!"
Cozy dog friendly updated house in quiet village adjacent to park
Property grounds
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
10.0 out of 10, Exceptional, (69)
"Very beautiful place. Lovely to catch up with friends."
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Sun-loungers, beach towels
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
2.0 star property
9.6 out of 10, Exceptional, (15)
"We had a great time! "
Waterfront Goodspeed airport 2-bedroom house with AC, WiFi
Fridge, microwave, oven, stovetop
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
10.0 out of 10, Exceptional, (2)
"Property fit our needs well. Clean, convenient location, easy to access the places around town we needed to get to, and a helpful and responsive host."
The price is €431
includes taxes & fees
4 Nov - 5 Nov
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"Great"
Lovett 1-night trip
Posted 2 days ago
Best Western Hartford Hotel & Suites

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?

3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay: This holiday home rental outside of Portland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.