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Portland Vacation Rentals

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Vacation Rentals in Portland

Interior
2-bedroom Oasis in Portland

2-bedroom Oasis in Portland

2.0 star property
Portland
$521 nightly
The price is $589
Nov 18 - Nov 19
Total with taxes and fees
2-bedroom Oasis in Portland
Dining
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

Middletown
9.8 out of 10, Exceptional, (20)
"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.
$278 nightly
The price is $296
Nov 18 - Nov 19
Total with taxes and fees
#24 *Serenity* A Lakefront Cottage Retreat
Exterior
The Blue Back Bungalow

The Blue Back Bungalow

2.0 star property
West Hartford
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 18 - Nov 19
Total with taxes and fees
The Blue Back Bungalow
Fridge, microwave, oven, stovetop
#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House

Southington
9.8 out of 10, Exceptional, (8)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
$275 nightly
The price is $291
Nov 18 - Nov 19
Total with taxes and fees
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Exterior detail
Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!

East Haddam
9.4 out of 10, Exceptional, (34)
"The place was spotless and comfortable. Would highly recommend!"
United States
Jeanne Y.
$217 nightly
The price is $246
Dec 4 - Dec 5
Total with taxes and fees
Walk To Goodspeed Opera House!
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, (34)
"Comfortable and as described "
United States
Stephanie
$247 nightly
The price is $280
Nov 18 - Nov 19
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
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)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
$247 nightly
The price is $280
Nov 18 - Nov 19
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Beach nearby
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, (5)
"Place is nice would stay again "
United States
nic
$318 nightly
The price is $359
Nov 18 - Nov 19
Total with taxes and fees
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Exterior
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Killingworth
10.0 out of 10, Exceptional, (51)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
$617 nightly
The price is $698
Dec 15 - Dec 16
Total with taxes and fees
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Fridge, microwave, oven, stovetop
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)
"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.
$259 nightly
The price is $293
Nov 18 - Nov 19
Total with taxes and fees
Modern & Cozy Cape | 4 Bedroom House | Central Location
Interior
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Haddam
10.0 out of 10, Exceptional, (26)
"Overall wonderful experience, would highly recommend."
United States
Steven R.
$228 nightly
The price is $258
Nov 24 - Nov 25
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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

Wallingford Center
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.
$245 nightly
The price is $259
Nov 18 - Nov 19
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment
Outdoor dining
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.
$246 nightly
The price is $278
Nov 18 - Nov 19
Total with taxes and fees
Soothing 2-bedroom lower-level apartment in Berlin
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
Bloomfield
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
$530 nightly
The price is $601
Nov 25 - Nov 26
Total with taxes and fees
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Fridge, microwave, oven, coffee/tea maker
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

New Britain
7.6 out of 10, Good, (7)
" Not bad for the price "
United States
Audrey L.
$328 nightly
The price is $371
Nov 18 - Nov 19
Total with taxes and fees
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
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

Downtown Hartford
9.6 out of 10, Exceptional, (5)
"Cozy, clean, comfortable. Location is excellent and accessible to restaurants and venues. Highly recommended. "
United States
Jason B.
$170 nightly
The price is $193
Nov 18 - Nov 19
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

Wallingford Center
9.8 out of 10, Exceptional, (6)
"This is a very nice updated one-bedroom apartment in a central location. Restaurants are within walking distance. The building has an elevator. The kitchen has everything you need. I enjoyed my stay. Just one caveat: the train tracks run just behind the building. The trains aren’t constant, but they do blow their horn at the intersection. I brought earplugs, and the noise didn’t keep me from sleeping "
United States
Karen D.
$245 nightly
The price is $259
Nov 18 - Nov 19
Total with taxes and fees
All New 1BR with tons of Charm
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

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

Coventry Lake
9.6 out of 10, Exceptional, (38)
"Pet and family, friendly"
United States
Mary-Kate G
$294 nightly
The price is $333
Dec 3 - Dec 4
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$279 nightly
The price is $316
Nov 18 - Nov 19
Total with taxes and fees
Private Apartment in Berlin
Exterior
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, (80)
"Very nice cabins "
United States
Jairo
$159 nightly
The price is $183
Nov 19 - Nov 20
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

10/10 Excellent
"Excellent day. I will definitely return even though it is not as convenient for me as some of the other locations."
Kimberly 3-night trip
Posted 4 days ago
Hilton Garden Inn Hartford North/Bradley Int'l Airport

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?

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.