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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Portland holiday rentals

A compact kitchen with stainless steel appliances, a marble countertop, and a black coffee maker.

1. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is NZ$419
includes taxes & fees
16 Nov - 17 Nov
2BR Apartment Near Wesleyan 102
Veterans Park, near the house

2. 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 NZ$471
includes taxes & fees
1 Dec - 2 Dec
Family Stays: Middletown, CT
A modern kitchen with stainless steel appliances, a ceiling fan, and a marble countertop.

3. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is NZ$497
includes taxes & fees
16 Nov - 17 Nov
3 BR Apartment Near Wesleyan 201
A covered patio with two white plastic chairs and a small table, overlooking a residential area with houses and trees.

4. 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 NZ$470
includes taxes & fees
16 Nov - 17 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.

5. 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 NZ$450
includes taxes & fees
1 Dec - 2 Dec
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A cabin surrounded by a natural forest setting with a fire pit and picnic table.

6. 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, (223 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is NZ$348
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A hotel reception area with a receptionist, a guest, and a child.

7. 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 NZ$150
includes taxes & fees
16 Nov - 17 Nov
1 Queen Bed | Wethersfield
A hotel reception area with a receptionist, a guest, and a child.

8. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple rooms close to I-91 made travel convenient."
United States
Anonymous traveller
The price is NZ$150
includes taxes & fees
16 Nov - 17 Nov
1 Queen Bed | Smoking
Kitchen

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 NZ$464
includes taxes & fees
16 Nov - 17 Nov
Private Apartment in Berlin
A hotel reception area with a counter, a digital tablet, and a poster on the wall.

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 NZ$158
includes taxes & fees
16 Nov - 17 Nov
1 Queen Bed | Micfridge
A hotel reception area with a receptionist, a guest, and a child.

11. 2 Full Beds | Wethersfield

2 Full Beds | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (52 reviews)
"Fresh linens along with basic facilities suited my brief stop just right."
United States
Anonymous traveller
The price is NZ$160
includes taxes & fees
16 Nov - 17 Nov
2 Full Beds | Wethersfield
A hotel reception area with a receptionist, a guest, and a child.

12. 1 Full Bed | Deluxe, Micfridge, Smoking

1 Full Bed | Deluxe, Micfridge, Smoking
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"We enjoyed the double bed comfort and small seating area which worked fine after our daily outings. Close proximity to dining spots helped us grab meals easily."
United States
Anonymous traveller
The price is NZ$156
includes taxes & fees
29 Nov - 30 Nov
1 Full Bed | Deluxe, Micfridge, Smoking
A hotel room with a wooden floor, a bed with patterned bedding, a yellow armchair, and a view into the bathroom.

13. 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 NZ$158
includes taxes & fees
16 Nov - 17 Nov
1 Full Bed | Micfridge, Smoking
A hotel reception area with a receptionist, a guest, and a child.

14. 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 NZ$162
includes taxes & fees
16 Nov - 17 Nov
1 Queen Bed | Deluxe, Micfridge
A hotel reception area with a receptionist, a guest, and a child.

15. 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 NZ$170
includes taxes & fees
16 Nov - 17 Nov
2 Full Beds | Micfridge
A small room with a table and chairs, a television mounted on the wall, and a window with a view of a parking lot and buildings.

16. 1 Queen Bed | ADA/RI Shower/Micfridge

1 Queen Bed | ADA/RI Shower/Micfridge
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Got around town easily since it's close to Interstate 91. Parking was simple compared to other places I've tried nearby."
United States
Anonymous traveller
The price is NZ$158
includes taxes & fees
18 Nov - 19 Nov
1 Queen Bed | ADA/RI Shower/Micfridge
A compact hotel room with a desk, a microwave, a TV, and a bed with a patterned bedspread.

17. 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
The price is NZ$170
includes taxes & fees
19 Nov - 20 Nov
2 Full Beds | ADA/Tub/Micfridge
A kitchen with wooden cabinets, granite countertops, and a stainless steel sink.

18. Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"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
29 Nov - 30 Nov
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
A small room with a television, a table with chairs, a window, and a door leading outside.

19. 2 Full Beds | Micfridge | Smoking

2 Full Beds | Micfridge | Smoking
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Compact yet cozy accommodations met needs perfectly."
United States
Anonymous traveller
The price is NZ$170
includes taxes & fees
19 Nov - 20 Nov
2 Full Beds | Micfridge | Smoking
A living room with a blue sofa, patterned armchair, wooden coffee table, and a globe on a side table.

20. Brand New Platform #1

Brand New Platform #1
Wallingford Center
9.6 out of 10, Exceptional, (4 reviews)
"This is the second time we have stayed at this location, although it was a different "platform/room." Once again, a very nice stay. Room was perfect for the 2 of us, and all the right ameneties. This is a perfect location within Wallenford, with access to everything, whether walking or driving. The property is very well maintained, and feels very secure. "
United States
Cherie G.
Brand New Platform #1
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

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

8/10 Good
"The hotel is undergoing renovations so it's not as clean as it could be. The updated rooms are really nice but it needed a few things. 1) Rooms needs a hairdryer 2) also needs a 2nd trash can 3) Coffeemaker doesnt work right The breakfast was ok but it wasnt bad either. The bathrooms was tootier. Love the double shower heads and the toiletries. Helped with not having to pack my own. Overall I would stay here again. Hopefully it's cleaner after renovations are done. And the chemical rug smell goes away."
Channary 2-night trip
Posted 2 days ago
Clarion Inn North Haven - New Haven North

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$348 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?

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.