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

Portland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Portland vacation rentals

Veterans Park, near the house

1. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (31 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
$232 nightly
The price is $263
Oct 27 - Oct 28
Total with taxes and fees
Family Stays: Middletown, CT
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

2. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$248 nightly
The price is $281
Oct 5 - Oct 6
Total with taxes and fees
2BR Apartment Near Wesleyan 102
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.
$323 nightly
The price is $366
Oct 5 - Oct 6
Total with taxes and fees
3 BR Apartment Near Wesleyan 202
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

4. 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
$282 nightly
The price is $320
Nov 2 - Nov 3
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.

5. 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, (38 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.
$228 nightly
The price is $258
Oct 19 - Oct 20
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

6. 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.
$314 nightly
The price is $355
Nov 3 - Nov 4
Total with taxes and fees
3 BR Apartment Near Wesleyan 201
A cabin with a dining table set for two, a bicycle, and a small porch area.

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, (197 reviews)
"Great experience and the perfect environment"
United States
Stephanie
$175 nightly
The price is $201
Nov 2 - Nov 3
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern living room with a sofa, a dining table, and a massage chair.

8. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
$473 nightly
The price is $506
Oct 7 - Oct 8
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
Stairwell

9. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
$237 nightly
The price is $268
Oct 5 - Oct 6
Total with taxes and fees
Private Apartment in Berlin
A hotel room with a bed, a desk with a TV, and a bathroom visible through an open door.

10. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
$71 nightly
The price is $81
Nov 1 - Nov 2
Total with taxes and fees
1 Queen Bed | Wethersfield
A hotel room with a desk, chair, TV, two beds, and a window with curtains.

11. 2 Full Beds | Wethersfield

2 Full Beds | Wethersfield
Wethersfield
$75 nightly
The price is $87
Nov 1 - Nov 2
Total with taxes and fees
2 Full Beds | Wethersfield
A modern living room with a glass dining table, dark chairs, a sofa, and a ceiling fan.

12. 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
6.8 out of 10, (8 reviews)
" Not bad for the price "
United States
Audrey L.
$324 nightly
The price is $366
Oct 4 - Oct 5
Total with taxes and fees
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

13. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable with easy communication with host I recommend this unit to all who want to visit Wallingford or who desire to take the train to ny or Boston etc"
United States
DAVID B.
$277 nightly
The price is $295
Oct 4 - Oct 5
Total with taxes and fees
All New Studio apartment in center of town
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

14. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
$277 nightly
The price is $295
Oct 5 - Oct 6
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
A two-story house with a front porch, a garage, and a well-maintained lawn.

15. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
$735 nightly
The price is $831
Oct 5 - Oct 6
Total with taxes and fees
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern office space with a sofa, two round tables, and a coffee table. There are chairs around the tables, a rug on the floor, and a door in the background.

16. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
$823 nightly
The price is $931
Oct 4 - Oct 5
Total with taxes and fees
Conference Room Rental no sleeping arrangements
A hotel room with a bed, a desk with a chair, a television, a mirror, and a bathroom with a towel rack.

17. 1 Queen Bed | Micfridge

1 Queen Bed | Micfridge
Wethersfield
$74 nightly
The price is $86
Nov 1 - Nov 2
Total with taxes and fees
1 Queen Bed | Micfridge
A hotel room with a bed, bedside tables, a microwave, and a door leading to a bathroom.

18. 1 Full Bed | Deluxe, Micfridge, Smoking

1 Full Bed | Deluxe, Micfridge, Smoking
Wethersfield
$73 nightly
The price is $85
Nov 1 - Nov 2
Total with taxes and fees
1 Full Bed | Deluxe, Micfridge, Smoking
A hotel room with a bed, bedside table, TV, and a window with curtains.

19. 1 Full Bed | Micfridge, Smoking

1 Full Bed | Micfridge, Smoking
Wethersfield
$74 nightly
The price is $86
Nov 1 - Nov 2
Total with taxes and fees
1 Full Bed | Micfridge, Smoking
A small room with a table and chairs, a television mounted on the wall, and a window with a view of a parking lot and buildings.

20. 1 Queen Bed | ADA/RI Shower/Micfridge

1 Queen Bed | ADA/RI Shower/Micfridge
Wethersfield
$74 nightly
The price is $86
Nov 1 - Nov 2
Total with taxes and fees
1 Queen Bed | ADA/RI Shower/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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"The property was very safe and clean. The room was up to date and in good repair. Overall, very pleasant atmosphere. They had a good variety of quick eats for sale for late arrivals that missed a meal and didn't want to go out. The hot breakfast was pretty typical of Hampton's. Nice touch with check-in cookies and numerous breakfast to go bags for early check-outs."
Gordon 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Hartford/East Hartford

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 $201 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?

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.