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Portland Vacation Rentals

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Jan 9 - Jan 10
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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 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 ￥17,102
￥26,885 total
includes taxes & fees
Jan 13 - Jan 14
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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 reviews)
"Place is nice would stay again "
United States
nic
The price is ￥15,166
￥56,872 total
includes taxes & fees
Jan 12 - Jan 13
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
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 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 ￥21,338
￥46,034 total
includes taxes & fees
Jan 15 - Jan 16
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
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 reviews)
"It was great! Thank you :-) "
United States
Becki S.
The price is ￥18,671
￥42,653 total
includes taxes & fees
Jan 19 - Jan 20
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Beach nearby, beach towels
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
9.4 out of 10, Exceptional, (39 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is ￥23,692
￥49,996 total
includes taxes & fees
Jan 20 - Jan 21
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
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 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 ￥13,768
￥78,018 total
includes taxes & fees
Jan 25 - Jan 26
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
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 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 ￥19,205
￥50,288 total
includes taxes & fees
Jan 12 - Jan 13
Soothing 2-bedroom lower-level apartment in Berlin
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 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is ￥13,533
￥32,822 total
includes taxes & fees
Jan 13 - Jan 14
Central Chic Pad - with Free Parking, Heat & AC
Exterior
Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
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 ￥30,596
￥48,757 total
includes taxes & fees
Jan 12 - Jan 13
Walk To Goodspeed Opera House!
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
9.2 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 ￥13,274
￥25,620 total
includes taxes & fees
Jan 14 - Jan 15
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Property grounds
Charming Lakeview, 3 Bedroom home in Colchester

Charming Lakeview, 3 Bedroom home in Colchester

Charming Lakeview, 3 Bedroom home in Colchester
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 ￥29,937
￥59,061 total
includes taxes & fees
Jan 11 - Jan 12
Charming Lakeview, 3 Bedroom home in Colchester
Interior
The Historic Hideaway

The Historic Hideaway

The Historic Hideaway
2.0 star property
Avon
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 ￥8,630
￥38,086 total
includes taxes & fees
Jan 11 - Jan 12
The Historic Hideaway
Property grounds
Humble Abode #2

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥18,828
￥24,790 total
includes taxes & fees
Jan 11 - Jan 12
Humble Abode #2
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 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 ￥9,414
￥39,195 total
includes taxes & fees
Jan 12 - Jan 13
Sun Filled Lake House Living
Property grounds
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
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 ￥70,605
￥127,795 total
includes taxes & fees
Jan 12 - Jan 13
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
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 reviews)
"Had a nice stay at this VRBO. Cozy and quiet."
United States
James C.
The price is ￥13,500
￥48,880 total
includes taxes & fees
Jan 11 - Jan 12
Charming Luxury 1BR Near Downtown. Dog Friendly!
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 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 ￥15,847
￥46,231 total
includes taxes & fees
Jan 11 - Jan 12
Private Apartment in Berlin
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 reviews)
"Great stay"
United States
Josh H.
The price is ￥15,690
￥23,888 total
includes taxes & fees
Jan 11 - Jan 12
Lux Boutique Large Private LOFT Pratt St Hartford
Exterior
Family Stays: Middletown, CT

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
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 ￥19,613
￥36,519 total
includes taxes & fees
Feb 2 - Feb 3
Family Stays: Middletown, CT
Dining
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!

LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
2.0 star property
Clinton
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 ￥21,888
￥82,480 total
includes taxes & fees
Jan 13 - Jan 14
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

Holiday Inn Express Hartford South - Rocky Hill by IHG

Holiday Inn Express Hartford South - Rocky Hill by IHG

10/10 Excellent
"Great staff. Only issue door would not latch close but they immediately offered to switch rooms "
georgia 1-night trip
Posted 4 days ago
Holiday Inn Express Hartford South - Rocky Hill by IHG

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
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  • 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.