Portland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Portland vacation rentals

A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

1. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (7 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$245 nightly
The price is $279
Nov 6 - Nov 7
Total with taxes and fees
2BR Apartment Near Wesleyan 102
A modern kitchen with a central island, white cabinetry, stainless steel appliances, and a wooden floor.

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.
$282 nightly
The price is $322
Nov 6 - Nov 7
Total with taxes and fees
2BR Apartment Near Wesleyan 301
A dining room with a rectangular table and four chairs, a window with blinds, a recessed ceiling light, and a wall-mounted air conditioning unit.

3. 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.
3 BR Apartment Near Wesleyan 202
A room with a patterned rug, a door leading to a kitchen, and a window with blinds.

4. 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.
$237 nightly
The price is $270
Nov 16 - Nov 17
Total with taxes and fees
Family Stays: Middletown, CT
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

5. 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
$264 nightly
The price is $301
Nov 9 - Nov 10
Total with taxes and fees
Private Apt in Middletown-Wesleyan 101
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

6. 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.
$221 nightly
The price is $252
Dec 1 - Dec 2
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

7. 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 traveler
$77 nightly
The price is $89
Nov 5 - Nov 6
Total with taxes and fees
1 Queen Bed | Micfridge
A glass enclosure with a view of a forest interior, including a bed and a small table with items.

8. 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, (216 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
$189 nightly
The price is $217
Nov 30 - Dec 1
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

9. 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 traveler
$73 nightly
The price is $84
Nov 5 - Nov 6
Total with taxes and fees
1 Queen Bed | Smoking
Stairwell

10. 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.
$235 nightly
The price is $268
Nov 9 - Nov 10
Total with taxes and fees
Private Apartment in Berlin
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

11. 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 traveler
$73 nightly
The price is $84
Nov 9 - Nov 10
Total with taxes and fees
1 Queen Bed | Wethersfield
A hotel room with a neatly made bed, a bedside table with a lamp, and a window with patterned curtains.

12. 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 traveler
$78 nightly
The price is $90
Nov 5 - Nov 6
Total with taxes and fees
2 Full Beds | Wethersfield
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

13. 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 traveler
$77 nightly
The price is $89
Nov 5 - Nov 6
Total with taxes and fees
1 Queen Bed | ADA/RI Shower/Micfridge
A hotel room with a neatly made bed, a bedside table with a lamp, and a window with patterned curtains.

14. 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 traveler
$83 nightly
The price is $95
Nov 5 - Nov 6
Total with taxes and fees
2 Full Beds | Micfridge
Three individuals in blue aprons walking outside a building with a staircase and a red umbrella in the background.

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 traveler
$79 nightly
The price is $91
Nov 5 - Nov 6
Total with taxes and fees
1 Queen Bed | Deluxe, Micfridge
An outdoor kitchen area with a stone fireplace, grill, and built-in refrigerator.

16. Cozy 1 bedroom private farmhouse apartment

Cozy 1 bedroom private farmhouse apartment
Durham
$233 nightly
The price is $265
Nov 30 - Dec 1
Total with taxes and fees
Cozy 1 bedroom private farmhouse apartment
A hotel room with a wooden floor, a bed with patterned bedding, a yellow armchair, and a view into the bathroom.

17. 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 traveler
$77 nightly
The price is $89
Nov 9 - Nov 10
Total with taxes and fees
1 Full Bed | Micfridge, Smoking
A hotel room with two beds, a window with curtains, and a wall-mounted heater.

18. 2 Full Beds | Micfridge | Smoking

2 Full Beds | Micfridge | Smoking
Wethersfield
10.0 out of 10, Exceptional, (47 reviews)
"Compact yet cozy accommodations met needs perfectly."
United States
Anonymous traveler
$83 nightly
The price is $95
Nov 8 - Nov 9
Total with taxes and fees
2 Full Beds | Micfridge | Smoking
A hotel room with a bed, bedside tables, a microwave, a refrigerator, a toilet, and a shower.

19. 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 traveler
$76 nightly
The price is $88
Nov 15 - Nov 16
Total with taxes and fees
1 Full Bed | Deluxe, Micfridge, Smoking
A hotel room with two beds, a window with curtains, and a wall-mounted heater.

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 traveler
$83 nightly
The price is $95
Nov 17 - Nov 18
Total with taxes and fees
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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Find vacation rentals that suit your style

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Top Portland Hotel Reviews

A brick building with a sign that reads "Inn at Middletown."
Inn at Middletown

Inn at Middletown

Inn at Middletown
Washington Street Historic District

10/10 Excellent

Everything was fine except the parking situation. Valet is not preferable and street parking becomes a problem.
United States
Anonymous traveler
Reviewed October 24, 2017
Inn at Middletown

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 $84 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.

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.

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