A river with a large bridge and a small boat on the shore.

Portland Vacation Rentals

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Our top choices for Portland vacation rentals

1. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (8 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is CA $144
CA $346 total
includes taxes & fees
Nov 10 - Nov 11
2BR Apartment Near Wesleyan 102

2. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
9.6 out of 10, Exceptional, (4 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is CA $139
CA $381 total
includes taxes & fees
Nov 11 - Nov 12
2BR Apartment Near Wesleyan 301

3. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is CA $226
CA $469 total
includes taxes & fees
Nov 10 - Nov 11
3 BR Apartment Near Wesleyan 201

4. 2BR Apartment Near Wesleyan 303

2BR Apartment Near Wesleyan 303
Washington Street Historic District
The price is CA $215
CA $476 total
includes taxes & fees
Nov 10 - Nov 11
2BR Apartment Near Wesleyan 303

5. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (34 reviews)
"Gilbert is an amazing host! I highly recommend staying here if you are visiting Middletown."
United States
Audrey F.
The price is CA $191
CA $359 total
includes taxes & fees
Nov 16 - Nov 17
Family Stays: Middletown, CT

6. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.2 out of 10, Good, (5 reviews)
"Very clean. No frills."
United States
Kristoph
The price is CA $144
CA $387 total
includes taxes & fees
Nov 10 - Nov 11
Private Apt in Middletown-Wesleyan 101

7. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is CA $179
CA $271 total
includes taxes & fees
Dec 8 - Dec 9
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

8. 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
The price is CA $158
CA $458 total
includes taxes & fees
Nov 11 - Nov 12
3 BR Apartment Near Wesleyan 202

9. 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, (40 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is CA $177
CA $359 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

10. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Quick check-in and quiet room helped us get good rest before hitting the road again."
United States
Anonymous traveller
The price is CA $103
CA $118 total
includes taxes & fees
Nov 10 - Nov 11
1 Queen Bed | Wethersfield

11. 2 Full Beds | Wethersfield

2 Full Beds | Wethersfield
Wethersfield
10.0 out of 10, Exceptional, (52 reviews)
"My short stopover went well, beds were supportive but not too firm, setting remained calm despite being next to interstate."
United States
Anonymous traveller
The price is CA $110
CA $126 total
includes taxes & fees
Nov 10 - Nov 11
2 Full Beds | Wethersfield

12. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
8.8 out of 10, Excellent, (8 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is CA $150
CA $358 total
includes taxes & fees
Nov 10 - Nov 11
Private Apartment in Berlin

13. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Quick stop, quiet room near the highway."
United States
Anonymous traveller
The price is CA $108
CA $125 total
includes taxes & fees
Nov 10 - Nov 11
1 Queen Bed | Micfridge

14. 1 Full Bed | Deluxe, Micfridge, Smoking

1 Full Bed | Deluxe, Micfridge, Smoking
Wethersfield
10.0 out of 10, Exceptional, (51 reviews)
"Good value for what you get here. Clean room with a fridge and TV included."
United States
Anonymous traveller
The price is CA $107
CA $123 total
includes taxes & fees
Nov 10 - Nov 11
1 Full Bed | Deluxe, Micfridge, Smoking

15. 1 Queen Bed | Deluxe, Micfridge

1 Queen Bed | Deluxe, Micfridge
Wethersfield
10.0 out of 10, Exceptional, (53 reviews)
"Rooms were peaceful and set away from main street traffic for a restful stay."
United States
Anonymous traveller
The price is CA $111
CA $128 total
includes taxes & fees
Nov 10 - Nov 11
1 Queen Bed | Deluxe, Micfridge

16. 2 Full Beds | Micfridge

2 Full Beds | Micfridge
Wethersfield
10.0 out of 10, Exceptional, (53 reviews)
"Bed felt very comfortable compared to other motels I've stayed at around here before."
United States
Anonymous traveller
The price is CA $117
CA $134 total
includes taxes & fees
Nov 10 - Nov 11
2 Full Beds | Micfridge

17. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple rooms close to I-91 made travel convenient."
United States
Anonymous traveller
The price is CA $103
CA $118 total
includes taxes & fees
Nov 10 - Nov 11
1 Queen Bed | Smoking

18. 1 Full Bed | Micfridge, Smoking

1 Full Bed | Micfridge, Smoking
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Parking was simple and convenient throughout our visit with good access anytime during the day."
United States
Anonymous traveller
The price is CA $108
CA $125 total
includes taxes & fees
Nov 11 - Nov 12
1 Full Bed | Micfridge, Smoking

19. 1 Queen Bed | ADA/RI Shower/Micfridge

1 Queen Bed | ADA/RI Shower/Micfridge
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"The room was clean with a smooth check-in experience!"
United States
Anonymous traveller
The price is CA $108
CA $125 total
includes taxes & fees
Nov 11 - Nov 12
1 Queen Bed | ADA/RI Shower/Micfridge

20. 2 Full Beds | ADA/Tub/Micfridge

2 Full Beds | ADA/Tub/Micfridge
Wethersfield
10.0 out of 10, Exceptional, (49 reviews)
"Simple, straightforward stay here with everything you need."
United States
Anonymous traveller
The price is CA $117
CA $134 total
includes taxes & fees
Nov 12 - Nov 13
2 Full Beds | ADA/Tub/Micfridge
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Cabin Love at the Lake: This vacation home rental outside of Portland offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.