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Portland Vacation Rentals

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Oct 26 - Oct 27
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Oct 31 - Nov 2
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Nov 7 - Nov 9

Vacation Rentals in Portland

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (76)
"Very nice cabins "
United States
Jairo
$189 nightly
The price is $217
Oct 28 - Oct 29
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Beach nearby
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (3)
"This was a great find so close to home when my family needed a place to stay for a week. The house was clean, inviting and the communication with the property manager was amazing! Very fast to respond!"
United States
Courtney H.
$317 nightly
The price is $358
Nov 5 - Nov 6
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
9.8 out of 10, Exceptional, (34)
"Comfortable and as described "
United States
Stephanie
$259 nightly
The price is $293
Oct 28 - Oct 29
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin
Soothing 2-bedroom lower-level apartment in 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.
$235 nightly
The price is $266
Oct 28 - Oct 29
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Smart TV
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
2.0 star property
10.0 out of 10, Exceptional, (4)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
$155 nightly
The price is $175
Oct 30 - Oct 31
Total with taxes and fees
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$155 nightly
The price is $175
Oct 28 - Oct 29
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Fridge, microwave, oven, stovetop
Family Stays: Middletown, CT
Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (16)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
$172 nightly
The price is $195
Nov 4 - Nov 5
Total with taxes and fees
Family Stays: Middletown, CT
1 bedroom, iron/ironing board, WiFi, bed sheets
Once the old Schools house now a newly furnished Apartment
Once the old Schools house now a newly furnished Apartment
9.0 out of 10, Wonderful, (13)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
$264 nightly
The price is $281
Oct 31 - Nov 1
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Outdoor dining
The Sun Filled Cozy Creamery
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (22)
"Nice,cozy and a reasonable rate."
United States
Rachelle B.
$257 nightly
The price is $275
Oct 29 - Oct 30
Total with taxes and fees
The Sun Filled Cozy Creamery
Exterior detail
The Blue Back Bungalow
The Blue Back Bungalow
2.0 star property
9.4 out of 10, Exceptional, (16)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
$299 nightly
The price is $317
Nov 24 - Nov 25
Total with taxes and fees
The Blue Back Bungalow
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
9.6 out of 10, Exceptional, (4)
"Cozy, clean, comfortable. Location is excellent and accessible to restaurants and venues. Highly recommended. "
United States
Jason B.
$177 nightly
The price is $200
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
8.8 out of 10, Excellent, (48)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
$306 nightly
The price is $347
Nov 11 - Nov 12
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, oven, stovetop
New 1BR Great Location Center of Town
New 1BR Great Location Center of Town
10.0 out of 10, Exceptional, (2)
"Perfect spot for Oakdale Theater. Everything was as described and we were very comfortable. "
United States
Sarah W.
$271 nightly
The price is $288
Oct 28 - Oct 29
Total with taxes and fees
New 1BR Great Location Center of Town
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (6)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
$217 nightly
The price is $245
Oct 28 - Oct 29
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.6 out of 10, Exceptional, (37)
"Pet and family, friendly"
United States
Mary-Kate G
$314 nightly
The price is $356
Nov 3 - Nov 4
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, oven, stovetop
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Charming 3-Bedroom Home with Modern Comforts in West Hartford
2.0 star property
9.0 out of 10, Wonderful, (8)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
$240 nightly
The price is $272
Oct 29 - Oct 30
Total with taxes and fees
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC
Central Chic Pad - with Free Parking, Heat & AC
9.4 out of 10, Exceptional, (6)
"Spent the weekend of the 4th here in CT. The apartment building itself is a little iffy and the stairwell to the apartment left a lot to be desired but the room itself was very nice and well supplied with usable amenities. We really only needed the room to sleep at night so it suited our needs quite nicely. Given the lack of nice hotels in the area we would be more than happy to stay here again."
United States
Brenda M.
$227 nightly
The price is $244
Nov 3 - Nov 4
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
Fridge, microwave, oven, stovetop
Modern & Cozy Cape | 4 Bedroom House | Central Location
Modern & Cozy Cape | 4 Bedroom House | Central Location
10.0 out of 10, Exceptional, (5)
"We had a great stay in this house. It provided everything we needed for a comfortable and enjoyable visit. All the rooms were clean, tidy, and well-maintained, creating a welcoming environment. The host was exceptionally helpful and quick to respond to any questions or needs we had, which made our experience even better. We highly recommend this house for anyone looking for a hassle-free and pleasant stay."
Sweden
David S.
$255 nightly
The price is $289
Oct 28 - Oct 29
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
1 bedroom, iron/ironing board, WiFi, bed sheets
All New Studio apartment in center of town
All New Studio apartment in center of town
10.0 out of 10, Exceptional, (1)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
$271 nightly
The price is $288
Oct 28 - Oct 29
Total with taxes and fees
All New Studio apartment in center of town
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

Avon Old Farms Hotel

Avon Old Farms Hotel

10/10 Excellent
"Very pleasant. Breakfast OK only concern for tin. Wish for grab bars to feel safe. Maintenance staff very friendly and accommodating "
John 2-night trip
Posted 23 hours ago
Avon Old Farms Hotel

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 $158 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?

Private Apartment in Berlin: This vacation home rental outside of Portland is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.