Photo by Rick Bucchino

Portland Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Portland holiday rentals

View from property
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (99 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is HK$850
HK$1,336 total
includes taxes & fees
13 Jan - 14 Jan
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Holiday Home in Salem

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (6 reviews)
"Place is nice would stay again "
United States
nic
The price is HK$753
HK$2,825 total
includes taxes & fees
12 Jan - 13 Jan
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Holiday Home in Coventry Lake

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
9.8 out of 10, Exceptional, (35 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is HK$1,044
HK$2,277 total
includes taxes & fees
21 Jan - 22 Jan
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
8.8 out of 10, Excellent, (48 reviews)
"It was great! Thank you :-) "
United States
Becki S.
The price is HK$951
HK$2,146 total
includes taxes & fees
19 Jan - 20 Jan
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Beach nearby, beach towels
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Cabin in Coventry Lake

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.4 out of 10, Exceptional, (39 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is HK$1,177
HK$2,499 total
includes taxes & fees
20 Jan - 21 Jan
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Holiday Home in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
10.0 out of 10, Exceptional, (1 review)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is HK$680
HK$3,852 total
includes taxes & fees
25 Jan - 26 Jan
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
10.0 out of 10, Exceptional, (1 review)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is HK$954
HK$2,498 total
includes taxes & fees
12 Jan - 13 Jan
Soothing 2-bedroom lower-level apartment in Berlin
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Apartment in Manchester

Central Chic Pad - with Free Parking, Heat & AC
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is HK$672
HK$1,631 total
includes taxes & fees
13 Jan - 14 Jan
Central Chic Pad - with Free Parking, Heat & AC
Exterior
Walk To Goodspeed Opera House!

Apartment in East Haddam

Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (34 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is HK$1,520
HK$2,422 total
includes taxes & fees
12 Jan - 13 Jan
Walk To Goodspeed Opera House!
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Apartment in Cheshire

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.2 out of 10, Wonderful, (15 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is HK$659
HK$1,273 total
includes taxes & fees
14 Jan - 15 Jan
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Property grounds
Charming Lakeview, 3 Bedroom home in Colchester

Holiday Home in Colchester

Charming Lakeview, 3 Bedroom home in Colchester
10.0 out of 10, Exceptional, (1 review)
"Property was perfect for our Christmas break - very clean and tidy, had everything needed. Beds are comfortable and rooms feel spacious. Check-in was a breeze. Water pressure is a little low in the shower but the owners are aware of the issue. You can't go wrong with staying here!"
United States
Meagan P.
The price is HK$1,487
HK$2,934 total
includes taxes & fees
12 Jan - 13 Jan
Charming Lakeview, 3 Bedroom home in Colchester
Interior
The Historic Hideaway

Apartment in Avon

The Historic Hideaway
2.0 star property
7.0 out of 10, Good, (2 reviews)
"House exactly as listed. We had a question and the property owner replied instantly - great communication. Close to Talcott Mountain which was an amazing hike with beautiful views. "
United States
Nicole M.
The price is HK$437
HK$1,909 total
includes taxes & fees
12 Jan - 13 Jan
The Historic Hideaway
Property grounds
Humble Abode #2

Apartment in Manchester Center

Humble Abode #2
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$935
HK$1,232 total
includes taxes & fees
12 Jan - 13 Jan
Humble Abode #2
Property grounds
Sun Filled Lake House Living

Holiday Home in Avon

Sun Filled Lake House Living
2.0 star property
6.0 out of 10, (3 reviews)
"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"
United States
Joseph C.
The price is HK$475
HK$1,957 total
includes taxes & fees
12 Jan - 13 Jan
Sun Filled Lake House Living
Property grounds
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Cabin in Killingworth

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
10.0 out of 10, Exceptional, (54 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is HK$3,508
HK$6,349 total
includes taxes & fees
12 Jan - 13 Jan
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Fridge, microwave, stovetop, coffee/tea maker
Charming Luxury 1BR Near Downtown. Dog Friendly!

Apartment in Manchester

Charming Luxury 1BR Near Downtown. Dog Friendly!
9.4 out of 10, Exceptional, (11 reviews)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
The price is HK$666
HK$2,397 total
includes taxes & fees
12 Jan - 13 Jan
Charming Luxury 1BR Near Downtown. Dog Friendly!
Interior
Private Apartment in Berlin

Holiday Home in Berlin

Private Apartment in Berlin
2.0 star property
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is HK$538
HK$1,979 total
includes taxes & fees
12 Jan - 13 Jan
Private Apartment in Berlin
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Apartment in Downtown Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
8.6 out of 10, Excellent, (26 reviews)
"Great stay"
United States
Josh H.
The price is HK$779
HK$1,187 total
includes taxes & fees
12 Jan - 13 Jan
Lux Boutique Large Private LOFT Pratt St Hartford
Exterior
Family Stays: Middletown, CT

Holiday Home in Middletown

Family Stays: Middletown, CT
10.0 out of 10, Exceptional, (19 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is HK$974
HK$1,814 total
includes taxes & fees
2 Feb - 3 Feb
Family Stays: Middletown, CT
Dining
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

Holiday Home in Clinton

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is HK$1,087
HK$4,097 total
includes taxes & fees
13 Jan - 14 Jan
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
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

Red Roof Inn Meriden

Red Roof Inn Meriden

10/10 Excellent
"Y"
Michael 1-night trip
Posted 4 days ago
Red Roof Inn Meriden

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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of Portland offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

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.