Portland Vacation Rentals

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Our top choices for Portland vacation rentals

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (97)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
$141 nightly
The price is $162
Jan 7 - Jan 8
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Outdoor dining
The Historic Hideaway

The Historic Hideaway

The Historic Hideaway
2.0 star property
Avon
7.0 out of 10, Good, (2)
"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.
$233 nightly
The price is $245
Jan 9 - Jan 10
Total with taxes and fees
The Historic Hideaway
Beach nearby
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6)
"Place is nice would stay again "
United States
nic
$328 nightly
The price is $370
Jan 5 - Jan 6
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Property grounds
Humble Abode #2

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
$140 nightly
The price is $158
Jan 4 - Jan 5
Total with taxes and fees
Humble Abode #2
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (14)
"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.
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (48)
"It was great! Thank you :-) "
United States
Becki S.
$249 nightly
The price is $282
Jan 4 - Jan 5
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
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

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.6 out of 10, Exceptional, (5)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
United States
Hoyt
$170 nightly
The price is $193
Jan 4 - Jan 5
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

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, (1)
"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 4 - Jan 5
Total with taxes and fees
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (35)
"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.
$272 nightly
The price is $309
Jan 12 - Jan 13
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
$298 nightly
The price is $338
Jan 12 - Jan 13
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.6 out of 10, Excellent, (24)
"Great stay"
United States
Josh H.
$135 nightly
The price is $152
Jan 4 - Jan 5
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1)
"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 5 - Jan 6
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Fridge, microwave, stovetop, coffee/tea maker
Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (11)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
$274 nightly
The price is $310
Jan 4 - Jan 5
Total with taxes and fees
Charming Luxury 1BR Near Downtown. Dog Friendly!
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"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.
$266 nightly
The price is $301
Jan 4 - Jan 5
Total with taxes and fees
Private Apartment in Berlin
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (7)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
$271 nightly
The price is $288
Jan 4 - Jan 5
Total with taxes and fees
All New 1BR with tons of Charm
Smart TV
Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
$226 nightly
The price is $243
Feb 1 - Feb 2
Total with taxes and fees
Premier League Pad - with Free Parking, Heat & AC
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC
Downtown Hartford
8.6 out of 10, Excellent, (11)
"Great location, very nice and clean. "
United States
Manuel M.
$135 nightly
The price is $152
Jan 4 - Jan 5
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
$197 nightly
The price is $210
Jan 13 - Jan 14
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
Smart TV, fireplace
Sun Filled Lake House Living

Sun Filled Lake House Living

Sun Filled Lake House Living
2.0 star property
Avon
6.0 out of 10, (3)
"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 6 - Jan 7
Total with taxes and fees
Sun Filled Lake House Living
Smart TV
Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
2.0 star property
South Windsor
$79 nightly
The price is $88
Jan 11 - Jan 12
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
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

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

10/10 Excellent
"Friendly staff , coffee always available "
Marc 7-night trip
Posted 16 hours ago
Holiday Inn Cheshire - Southington by IHG

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.

Explore a world of travel with Expedia

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.