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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Portland holiday rentals

9.6 out of 10, Exceptional, (101 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is €147
includes taxes & fees
19 Jan - 20 Jan
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is €320
includes taxes & fees
15 Jan - 16 Jan
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
9.8 out of 10, Exceptional, (35 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is €254
includes taxes & fees
20 Jan - 21 Jan
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
8.8 out of 10, Excellent, (48 reviews)
"It was great! Thank you :-) "
United States
Becki S.
The price is €251
includes taxes & fees
22 Jan - 23 Jan
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.4 out of 10, Exceptional, (39 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is €260
includes taxes & fees
20 Jan - 21 Jan
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
10.0 out of 10, Exceptional, (1 review)
"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 €434
includes taxes & fees
25 Jan - 26 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is €283
includes taxes & fees
14 Jan - 15 Jan
Soothing 2-bedroom lower-level apartment in Berlin
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is €183
includes taxes & fees
9 Feb - 10 Feb
Central Chic Pad - with Free Parking, Heat & AC

Apartment in East Haddam

Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (34 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is €173
includes taxes & fees
15 Jan - 16 Jan
Walk To Goodspeed Opera House!
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is €144
includes taxes & fees
14 Jan - 15 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
10.0 out of 10, Exceptional, (1 review)
"Property was perfect for our Christmas break - very clean and tidy, had everything needed. Beds are comfortable and rooms feel spacious. Check-in was a breeze. Water pressure is a little low in the shower but the owners are aware of the issue. You can't go wrong with staying here!"
United States
Meagan P.
Charming Lakeview, 3 Bedroom home in Colchester

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is €215
includes taxes & fees
14 Jan - 15 Jan
The Historic Hideaway

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is €139
includes taxes & fees
9 Feb - 10 Feb
Humble Abode #2

Holiday Home in Avon

Sun Filled Lake House Living
2.0 star property
6.0 out of 10, (3 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is €220
includes taxes & fees
14 Jan - 15 Jan
Sun Filled Lake House Living
10.0 out of 10, Exceptional, (54 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is €718
includes taxes & fees
14 Jan - 15 Jan
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
9.4 out of 10, Exceptional, (11 reviews)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
The price is €251
includes taxes & fees
14 Jan - 15 Jan
Charming Luxury 1BR Near Downtown. Dog Friendly!

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is €260
includes taxes & fees
14 Jan - 15 Jan
Private Apartment in Berlin
8.6 out of 10, Excellent, (26 reviews)
"Great stay"
United States
Josh H.
The price is €134
includes taxes & fees
8 Feb - 9 Feb
Lux Boutique Large Private LOFT Pratt St Hartford

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (19 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is €208
includes taxes & fees
2 Feb - 3 Feb
Family Stays: Middletown, CT
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Portland Hotel Reviews

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 €134 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Portland offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, 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.