A river with a large bridge and a small boat on the shore.

Portland Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Portland holiday rentals

A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

1. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is AU$349
includes taxes & fees
3 Nov - 4 Nov
Family Stays: Middletown, CT
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

2. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
2BR Apartment Near Wesleyan 102
A spacious living room with a sectional sofa, a coffee table, and a dartboard on the wall.

3. 2BR Apartment Near Wesleyan 303

2BR Apartment Near Wesleyan 303
Washington Street Historic District
2BR Apartment Near Wesleyan 303
A modern living room with a leather sofa, a dining table with chairs, a kitchen area with white cabinets, and a chandelier.

4. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
The price is AU$637
includes taxes & fees
3 Nov - 4 Nov
#29 - Modern 5 Bedroom/2 Bath
A modern office space with a sofa, two round tables, and a coffee table. There are chairs around the tables, a rug on the floor, and a door in the background.

5. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is AU$1,243
includes taxes & fees
15 Nov - 16 Nov
Conference Room Rental no sleeping arrangements
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

6. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Very clean. No frills."
United States
Kristoph
The price is AU$393
includes taxes & fees
4 Nov - 5 Nov
Private Apt in Middletown-Wesleyan 101
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

7. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (40 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is AU$360
includes taxes & fees
1 Dec - 2 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A glass enclosure with a view of a forest interior, including a bed and a small table with items.

8. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (214 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is AU$273
includes taxes & fees
1 Dec - 2 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Stairwell

9. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is AU$367
includes taxes & fees
9 Nov - 10 Nov
Private Apartment in Berlin
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

10. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Quick stop, quiet room near the highway."
United States
Anonymous traveller
The price is AU$126
includes taxes & fees
3 Nov - 4 Nov
1 Queen Bed | Micfridge
A modern kitchen with a central island, bar stools, and pendant lighting.

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

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (35 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is AU$1,611
includes taxes & fees
3 Nov - 4 Nov
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A hotel room with a wooden floor, a bed with patterned bedding, a yellow armchair, and a view into the bathroom.

12. 1 Full Bed | Micfridge, Smoking

1 Full Bed | Micfridge, Smoking
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Parking was simple and convenient throughout our visit with good access anytime during the day."
United States
Anonymous traveller
The price is AU$126
includes taxes & fees
5 Nov - 6 Nov
1 Full Bed | Micfridge, Smoking
A modern living room with a glass dining table, dark chairs, a sofa, and a ceiling fan.

13. Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New Britain
6.8 out of 10, (8 reviews)
" Not bad for the price "
United States
Audrey L.
The price is AU$506
includes taxes & fees
15 Nov - 16 Nov
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
A living room with a sectional sofa, a glass coffee table, and a patterned rug.

14. Comfortable central home away from home

Comfortable central home away from home
Meriden
The price is AU$822
includes taxes & fees
15 Nov - 16 Nov
Comfortable central home away from home
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

15. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Quick check-in and quiet room helped us get good rest before hitting the road again."
United States
Anonymous traveller
The price is AU$119
includes taxes & fees
3 Nov - 4 Nov
1 Queen Bed | Wethersfield
A room with a fireplace, two sofas, a rug, and a robotic vacuum cleaner.

16. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is AU$924
includes taxes & fees
3 Nov - 4 Nov
The Cottage by the Woods -private getaway to relax
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

17. 1 Queen Bed | ADA/RI Shower/Micfridge

1 Queen Bed | ADA/RI Shower/Micfridge
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"The room was clean with a smooth check-in experience!"
United States
Anonymous traveller
The price is AU$126
includes taxes & fees
3 Nov - 4 Nov
1 Queen Bed | ADA/RI Shower/Micfridge
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

18. 1 Queen Bed | Deluxe, Micfridge

1 Queen Bed | Deluxe, Micfridge
Wethersfield
10.0 out of 10, Exceptional, (53 reviews)
"Rooms were peaceful and set away from main street traffic for a restful stay."
United States
Anonymous traveller
The price is AU$129
includes taxes & fees
3 Nov - 4 Nov
1 Queen Bed | Deluxe, Micfridge
A hotel room with a neatly made bed, a bedside table with a lamp, and a window with patterned curtains.

19. 2 Full Beds | Micfridge

2 Full Beds | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (53 reviews)
"Bed felt very comfortable compared to other motels I've stayed at around here before."
United States
Anonymous traveller
The price is AU$135
includes taxes & fees
3 Nov - 4 Nov
2 Full Beds | Micfridge
A hotel room with two beds, a window with curtains, and a wall-mounted heater.

20. 2 Full Beds | ADA/Tub/Micfridge

2 Full Beds | ADA/Tub/Micfridge
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple, straightforward stay here with everything you need."
United States
Anonymous traveller
2 Full Beds | ADA/Tub/Micfridge
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"Great place to stay for a concert"
Tanya 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Hartford/East Hartford

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 favourite 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 depend 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 AU$273 per night. Entering your travel dates in the search wizard might find you 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?

Cabin Love at the Lake: This holiday home rental outside of Portland offers a fireplace, a garden and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.