Portland Vacation Rentals

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Our top choices for Portland vacation rentals

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Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (99)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is ￥17,069
￥26,833 total
includes taxes & fees
Jan 8 - Jan 9
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Interior
The Historic Hideaway

The Historic Hideaway

The Historic Hideaway
2.0 star property
Avon
7.0 out of 10, Good, (2)
"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 ￥8,613
￥38,013 total
includes taxes & fees
Jan 9 - Jan 10
The Historic Hideaway
Interior
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
10.0 out of 10, Exceptional, (6)
"Place is nice would stay again "
United States
nic
The price is ￥15,138
￥56,923 total
includes taxes & fees
Jan 8 - Jan 9
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV, DVD player, books
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!

Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!

Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!
Manchester
10.0 out of 10, Exceptional, (2)
"Very nice apartment space, fully equipped."
United States
Michele M.
The price is ￥12,685
￥47,202 total
includes taxes & fees
Jan 8 - Jan 9
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!
Fridge, microwave, oven, stovetop
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (1)
"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 ￥13,656
￥77,385 total
includes taxes & fees
Jan 25 - Jan 26
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Property grounds
Humble Abode #2

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥18,793
￥24,744 total
includes taxes & fees
Jan 8 - Jan 9
Humble Abode #2
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1)
"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 ￥19,169
￥50,195 total
includes taxes & fees
Jan 12 - Jan 13
Soothing 2-bedroom lower-level apartment in Berlin
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (48)
"It was great! Thank you :-) "
United States
Becki S.
The price is ￥19,889
￥45,424 total
includes taxes & fees
Jan 8 - Jan 9
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, stovetop, coffee/tea maker
Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (11)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
The price is ￥13,389
￥48,167 total
includes taxes & fees
Jan 8 - Jan 9
Charming Luxury 1BR Near Downtown. Dog Friendly!
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (35)
"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 ￥21,142
￥45,769 total
includes taxes & fees
Jan 12 - Jan 13
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is ￥13,508
￥32,448 total
includes taxes & fees
Jan 13 - Jan 14
Central Chic Pad - with Free Parking, Heat & AC
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
New Britain
10.0 out of 10, Exceptional, (9)
" Heck-on was smooth and the kitchen and facilities were great. "
United States
Elizabeth P.
The price is ￥17,619
￥38,899 total
includes taxes & fees
Jan 12 - Jan 13
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Property grounds
Sun Filled Lake House Living

Sun Filled Lake House Living

Sun Filled Lake House Living
2.0 star property
Avon
6.0 out of 10, (3)
"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 ￥9,397
￥39,436 total
includes taxes & fees
Jan 8 - Jan 9
Sun Filled Lake House Living
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.6 out of 10, Exceptional, (5)
"Great place in a very nice part of the city. Walkable and lots to do around, and a reasonable parking garage right across the street. Apartment was clean, comfy and easily accessible."
United States
Hoyt
The price is ￥15,660
￥30,146 total
includes taxes & fees
Jan 12 - Jan 13
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Interior
Private Apartment in Berlin

Private Apartment in Berlin

Private Apartment in Berlin
2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"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 ￥16,601
￥47,203 total
includes taxes & fees
Jan 11 - Jan 12
Private Apartment in Berlin
Smart TV
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (15)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is ￥18,637
￥43,828 total
includes taxes & fees
Jan 25 - Jan 26
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
1 bedroom, iron/ironing board, free WiFi, bed sheets
#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2)
"I try to come up to Connecticut at least once a year if possible and this really worked out perfect for me first floor no steps easy to bring luggage in very comfortable. Would definitely come back and stay there again."
United States
Rodney L.
The price is ￥11,276
￥27,845 total
includes taxes & fees
Jan 8 - Jan 9
#2 *Beautiful 1 BR Apartment - Central CT*
Smart TV
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (14)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ￥13,249
￥25,573 total
includes taxes & fees
Jan 14 - Jan 15
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.6 out of 10, Excellent, (26)
"Great stay"
United States
Josh H.
The price is ￥15,660
￥23,842 total
includes taxes & fees
Feb 3 - Feb 4
Lux Boutique Large Private LOFT Pratt St Hartford
Interior
Modern Living: 1-BR Near XLCenter|ConventionCenter

Modern Living: 1-BR Near XLCenter|ConventionCenter

Modern Living: 1-BR Near XLCenter|ConventionCenter
Downtown Hartford
6.0 out of 10, (1)
The price is ￥13,782
￥31,322 total
includes taxes & fees
Jan 11 - Jan 12
Modern Living: 1-BR Near XLCenter|ConventionCenter
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

Inn at Middletown

Inn at Middletown

10/10 Excellent
"Staff was wonderful, lovely hotel"
Helen 1-night trip
Posted 2 days ago
Inn at Middletown

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 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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This vacation 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 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 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.