Photo by Rick Bucchino

Portland Vacation Rentals

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Our top choices for Portland vacation rentals

9.6 out of 10, Exceptional, (99 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
$149 nightly
The price is $171
Jan 13 - Jan 14
Total with taxes and fees
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
$322 nightly
The price is $363
Jan 13 - Jan 14
Total with taxes and fees
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.
$250 nightly
The price is $284
Jan 20 - Jan 21
Total with taxes and fees
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.
$239 nightly
The price is $272
Jan 19 - Jan 20
Total with taxes and fees
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
$270 nightly
The price is $306
Jan 20 - Jan 21
Total with taxes and fees
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.
$436 nightly
The price is $494
Jan 25 - Jan 26
Total with taxes and fees
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.
$283 nightly
The price is $321
Jan 12 - Jan 13
Total with taxes and fees
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
$196 nightly
The price is $209
Jan 13 - Jan 14
Total with taxes and fees
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.
$274 nightly
The price is $311
Jan 12 - Jan 13
Total with taxes and fees
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.
$145 nightly
The price is $163
Jan 14 - Jan 15
Total with taxes and fees
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.
$333 nightly
The price is $376
Jan 12 - Jan 13
Total with taxes and fees
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.
$232 nightly
The price is $244
Jan 12 - Jan 13
Total with taxes and fees
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
$140 nightly
The price is $158
Jan 12 - Jan 13
Total with taxes and fees
Humble Abode #2

Vacation 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.
$237 nightly
The price is $250
Jan 12 - Jan 13
Total with taxes and fees
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
$720 nightly
The price is $815
Jan 12 - Jan 13
Total with taxes and fees
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.
$272 nightly
The price is $308
Jan 12 - Jan 13
Total with taxes and fees
Charming Luxury 1BR Near Downtown. Dog Friendly!

Vacation 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.
$224 nightly
The price is $254
Jan 13 - Jan 14
Total with taxes and fees
Private Apartment in Berlin
8.6 out of 10, Excellent, (26 reviews)
"Great stay"
United States
Josh H.
$135 nightly
The price is $152
Jan 12 - Jan 13
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford

Vacation 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.
$205 nightly
The price is $233
Feb 2 - Feb 3
Total with taxes and fees
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.
$467 nightly
The price is $531
Jan 19 - Jan 20
Total with taxes and fees
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.
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Top Portland Hotel Reviews

Find out more about Portland

Everything you need to know about Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland vacation 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 vacation.

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 vacation rentals in Portland?

Yes, you can find vacation 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 the top vacation rental in Portland?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation 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 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 vacation rental in Portland like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Portland. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.