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

Portland Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Portland holiday rentals

A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

1. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
#24 Serenity A Lakefront Cottage Retreat
A bedroom with a bed, bedside tables, a radiator, and a door.

2. 2BR Apartment Near Wesleyan 303

2BR Apartment Near Wesleyan 303
Washington Street Historic District
The price is HK$1,256
HK$3,170 total
includes taxes & fees
13 Oct - 14 Oct
2BR Apartment Near Wesleyan 303
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

3. 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.
The price is HK$720
HK$1,909 total
includes taxes & fees
13 Oct - 14 Oct
2BR Apartment Near Wesleyan 102
Veterans Park, near the house

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (33 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
The price is HK$1,059
HK$2,009 total
includes taxes & fees
14 Oct - 15 Oct
Family Stays: Middletown, CT
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

5. 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 HK$832
HK$2,267 total
includes taxes & fees
14 Oct - 15 Oct
3 BR Apartment Near Wesleyan 201
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

6. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is HK$1,766
HK$2,258 total
includes taxes & fees
31 Oct - 1 Nov
“3BR Home Near Wesleyan & Downtown Middletown
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

7. 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 HK$890
HK$2,342 total
includes taxes & fees
13 Oct - 14 Oct
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.

8. 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.
The price is HK$981
HK$2,017 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A modern living room with a sofa, a dining table, and a massage chair.

9. #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.
The price is HK$1,398
HK$3,562 total
includes taxes & fees
13 Oct - 14 Oct
#29 - Modern 5 Bedroom/2 Bath
A cabin with a dining table set for two, a bicycle, and a small porch area.

10. 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, (201 reviews)
"Great experience and the perfect environment"
United States
Stephanie
The price is HK$1,059
HK$1,579 total
includes taxes & fees
10 Nov - 11 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Stairwell

11. 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.
The price is HK$720
HK$1,927 total
includes taxes & fees
13 Oct - 14 Oct
Private Apartment in Berlin
A person at a desk with a telephone, a notebook, and a pen.

12. 1 Queen Bed | Wethersfield

1 Queen Bed | Wethersfield
Wethersfield
The price is HK$536
HK$616 total
includes taxes & fees
6 Nov - 7 Nov
1 Queen Bed | Wethersfield
A hotel room with two beds, a wooden floor, and a bathroom with a mirror and sink.

13. 2 Full Beds | Wethersfield

2 Full Beds | Wethersfield
Wethersfield
The price is HK$574
HK$660 total
includes taxes & fees
6 Nov - 7 Nov
2 Full Beds | Wethersfield
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, (11 reviews)
"We really liked this property! Modernized apartment in an older home. Clean, comfortable, and close to family in the area. Karl was great to work with. We will stay here again next time we visit family!"
United States
Alan
The price is HK$926
HK$2,289 total
includes taxes & fees
13 Oct - 14 Oct
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

15. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is HK$926
HK$2,289 total
includes taxes & fees
13 Oct - 14 Oct
Once the old Schools house now a newly furnished Apartment
A kitchen with dark cabinets, a granite countertop, a black stove, a microwave, and a sink.

16. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (4 reviews)
"This property was very clean and comfortable; a nicely remodeled apartment in an older home. We had family members staying in one of the other apartments, so it was great to have them so close, but still had privacy. The location is conveniently located with plenty of restaurants nearby, and a short drive to fowntown dining and shops. Karl was an excellent host, griendly and very responsive. Would definitely stay here again!"
United States
Ryan
The price is HK$926
HK$2,289 total
includes taxes & fees
13 Oct - 14 Oct
Fully Furnished 1BR Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

17. 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.
The price is HK$926
HK$2,313 total
includes taxes & fees
16 Oct - 17 Oct
All New Studio apartment in center of town
A person at a desk with a telephone, a notebook, and a pen.

18. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Wethersfield
The price is HK$551
HK$634 total
includes taxes & fees
10 Nov - 11 Nov
1 Queen Bed | Smoking
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

19. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is HK$926
HK$2,289 total
includes taxes & fees
13 Oct - 14 Oct
All New Private and Cozy in great location
A hotel room with a bed, a desk with a chair, a flat-screen TV, a mirror, and a door with a lock.

20. 1 Full Bed | Micfridge, Smoking

1 Full Bed | Micfridge, Smoking
Wethersfield
The price is HK$582
HK$669 total
includes taxes & fees
10 Nov - 11 Nov
1 Full Bed | Micfridge, Smoking
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

Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

8/10 Good
"Great stay quit and peaceful with updated contemporary room style"
Chad 1-night trip
Posted less than an hour ago
Motel 6 Wethersfield, CT - Hartford

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

Frequently asked questions

Are there holiday rentals in Portland?

Yes, there are holiday 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 are some of the best holiday rentals that Portland has to offer?

Cabin Love at the Lake: This holiday home rental outside of Portland offers a fireplace, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 holiday rental in Portland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Portland. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.