Portland Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Portland vacation rentals

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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, (104 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 26 - Jan 27
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior

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 reviews)
"Place is nice would stay again "
United States
nic
$340 nightly
The price is $382
Jan 26 - Jan 27
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
Coventry Lake
9.8 out of 10, Exceptional, (36 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.
$215 nightly
The price is $244
Jan 26 - Jan 27
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Beach nearby

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 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
$219 nightly
The price is $248
Jan 24 - Jan 25
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
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.
$244 nightly
The price is $276
Jan 26 - Jan 27
Total with taxes and fees
Private Apartment in Berlin
Interior

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Windham
9.8 out of 10, Exceptional, (8 reviews)
"Nice home, good communication, town is very lovely"
United States
Arassely C.
$442 nightly
The price is $500
Jan 24 - Jan 25
Total with taxes and fees
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Smart TV

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

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
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.
$150 nightly
The price is $170
Jan 24 - Jan 25
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV, computer monitors

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
$197 nightly
The price is $210
Feb 3 - Feb 4
Total with taxes and fees
Central Chic Pad - with Free Parking, Heat & AC
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
Southington
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
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
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 25 - Jan 26
Total with taxes and fees
Humble Abode #2
Fridge, microwave, oven, stovetop

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
$209 nightly
The price is $225
Jan 25 - Jan 26
Total with taxes and fees
#26 Beautifully Renovated 2 BR Home
Property grounds

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 reviews)
"It was great! Thank you :-) "
United States
Becki S.
$291 nightly
The price is $330
Feb 23 - Feb 24
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
$249 nightly
The price is $282
Jan 25 - Jan 26
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
Terrace/patio

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
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.
$282 nightly
The price is $318
Jan 26 - Jan 27
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Dining

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Clinton
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.
$457 nightly
The price is $518
Feb 10 - Feb 11
Total with taxes and fees
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
Interior

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
Manchester Center
10.0 out of 10, Exceptional, (6 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
$163 nightly
The price is $184
Feb 1 - Feb 2
Total with taxes and fees
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
$87 nightly
The price is $97
Jan 26 - Jan 27
Total with taxes and fees
Entire guest suite in South Windsor, Connecticut
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
$316 nightly
The price is $339
Feb 18 - Feb 19
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Exterior

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
$198 nightly
The price is $224
Feb 2 - Feb 3
Total with taxes and fees
Family Stays: Middletown, CT
Property grounds

The little Chestnut. A charming historic apartment in Downtown Chester

The little Chestnut. A charming historic apartment in Downtown Chester
Chester Center
10.0 out of 10, Exceptional, (6 reviews)
"A lovely little place! Everything we needed, in a great location."
United States
Michael S.
$319 nightly
The price is $361
Jan 27 - Jan 28
Total with taxes and fees
The little Chestnut. A charming historic apartment in Downtown Chester
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

Best Western Manchester

Best Western Manchester

10/10 Excellent
"The staff was awesome, check in was quick and easy. The room was clean and the bed was super comfy."
Tina 1-night trip
Posted 1 day ago
Best Western Manchester

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.