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Portland Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Portland holiday rentals

Interior

1. Bristol Condo Near ESPN HQ & Lake Compounce!

Bristol Condo Near ESPN HQ & Lake Compounce!
Bristol
The price is HK$1,036
HK$2,431 total
includes taxes & fees
1 Sept - 2 Sept
Bristol Condo Near ESPN HQ & Lake Compounce!
Room

2. Belltown House at Airline Trail

Belltown House at Airline Trail
East Hampton
The price is HK$1,449
HK$3,654 total
includes taxes & fees
9 Sept - 10 Sept
Belltown House at Airline Trail
Interior

3. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
The price is HK$1,373
HK$2,462 total
includes taxes & fees
1 Sept - 2 Sept
Bristol Condo Near Espn HQ & Lake Compounce!
Iron/ironing board, WiFi, bed sheets

4. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
The price is HK$2,119
HK$5,024 total
includes taxes & fees
15 Aug - 16 Aug
The Cottage by the Woods -private getaway to relax
Living area

5. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
The price is HK$1,518
HK$2,374 total
includes taxes & fees
15 Aug - 16 Aug
Trumbull Apartments
Dining

6. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Excellent beds and clean."
United States
DANIEL M.
The price is HK$847
HK$2,094 total
includes taxes & fees
14 Aug - 15 Aug
2BR Apartment Near Wesleyan 102
Coffee/tea maker, fridge, microwave, oven

7. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (3 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 HK$847
HK$2,316 total
includes taxes & fees
14 Aug - 15 Aug
2BR Apartment Near Wesleyan 301
View from property

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, (177 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is HK$1,060
HK$1,941 total
includes taxes & fees
24 Aug - 25 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Smart TV, fireplace, books, music library

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, (35 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is HK$981
HK$2,009 total
includes taxes & fees
31 Aug - 1 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Dining

10. 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
Smart TV

11. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is HK$2,091
HK$4,272 total
includes taxes & fees
26 Aug - 27 Aug
#29 - Modern 5 Bedroom/2 Bath
Coffee/tea maker, fridge, microwave, oven

12. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is HK$847
HK$2,316 total
includes taxes & fees
14 Aug - 15 Aug
Private Apt in Middletown-Wesleyan 101
Property grounds

13. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is HK$1,130
HK$2,469 total
includes taxes & fees
7 Sept - 8 Sept
Lakeview Carriage House with Spectacular Sunset Views
Dining

14. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is HK$1,773
HK$3,515 total
includes taxes & fees
26 Aug - 27 Aug
3 BR Apartment Near Wesleyan 201
Coffee/tea maker, fridge, microwave, oven

15. “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 Aug - 1 Sept
“3BR Home Near Wesleyan & Downtown Middletown
TV

16. 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)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is HK$926
HK$2,320 total
includes taxes & fees
15 Aug - 16 Aug
Newly Remodeled 1-BR Close to Everything yet Very Private
Exterior

17. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is HK$926
HK$2,320 total
includes taxes & fees
29 Aug - 30 Aug
All New 1BR with tons of Charm
Interior

18. 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$1,177
HK$2,538 total
includes taxes & fees
1 Sept - 2 Sept
Private Apartment in Berlin
TV

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$2,312 total
includes taxes & fees
14 Aug - 15 Aug
All New Private and Cozy in great location
1 bedroom, iron/ironing board, WiFi, bed sheets

20. 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, (14 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$2,320 total
includes taxes & fees
15 Aug - 16 Aug
Once the old Schools house now a newly furnished Apartment
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

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

10/10 Excellent
"Great spot in Farmington"
Shawn 1-night trip
Posted 16 hours ago
Homewood Suites by Hilton Hartford-Farmington

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?

NEW Coastal Cottage 2 Miles to Beach + Lake Access: This holiday home rental outside of Portland is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.