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Portland Holiday Rentals

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Our top choices for Portland holiday rentals

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (160 reviews)
"Great stay! "
United States
Tanitra
The price is NZ$375
includes taxes & fees
27 July - 28 July
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

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, (44 reviews)
"We had an awesome stay for Thanksgiving week!"
United States
Jamie S.
The price is NZ$523
includes taxes & fees
1 July - 2 July
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, (51 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is NZ$670
includes taxes & fees
14 July - 15 July
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

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, (4 reviews)
"The apartment was perfect for my husband and me. It was clean and had everything we needed. The owners were very responsive when I had a question."
United States
Jenny T.
The price is NZ$575
includes taxes & fees
29 June - 30 June
Manchester 1-Bedroom Oasis APT Near Downtown Main Street. Pet-Friendly!

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (40 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 NZ$670
includes taxes & fees
1 July - 2 July
Lakefront - King - W&D - PetsOK - Kayaks - SUPs

The Blue Back Bungalow

The Blue Back Bungalow
West Hartford
9.4 out of 10, Exceptional, (18 reviews)
"Great location and pleasant area to walk to area restaurants and shops. Prompt and friendly communication with host who was very accommodating to our needs. We enjoyed our stay."
United States
Laurie R.
The price is NZ$546
includes taxes & fees
29 June - 30 June
The Blue Back Bungalow

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (156 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
The price is NZ$677
includes taxes & fees
26 July - 27 July
Go Jump in the Lake!

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is NZ$512
includes taxes & fees
28 July - 29 July
Newly Remodeled with deck. Close to town center

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)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is NZ$514
includes taxes & fees
11 July - 12 July
Newly Remodeled 1-BR Close to Everything yet Very Private

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is NZ$212
includes taxes & fees
1 July - 2 July
Entire guest suite in South Windsor, Connecticut

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, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is NZ$517
includes taxes & fees
5 July - 6 July
Once the old Schools house now a newly furnished Apartment

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 NZ$517
includes taxes & fees
29 June - 30 June
All New 1BR with tons of Charm

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is NZ$280
includes taxes & fees
29 June - 30 June
Humble Abode #2

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, (33 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is NZ$531
includes taxes & fees
20 July - 21 July
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

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, (20 reviews)
"Easy check in Rooms were comfortably spacious "
United States
Benjamin W.
The price is NZ$372
includes taxes & fees
29 June - 30 June
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is NZ$615
includes taxes & fees
23 July - 24 July
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

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 NZ$393
includes taxes & fees
6 July - 7 July
Central Chic Pad - with Free Parking, Heat & AC

Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is NZ$512
includes taxes & fees
18 July - 19 July
Fully Furnished 1BR Apartment

Peek-A-Boo View, Amston Lake

Peek-A-Boo View, Amston Lake
Lebanon
9.8 out of 10, Exceptional, (50 reviews)
"Enjoyed our time here, owner available and helpful"
United States
Kathleen C.
The price is NZ$675
includes taxes & fees
29 June - 30 June
Peek-A-Boo View, Amston Lake

#2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT*
Plainville
9.0 out of 10, Wonderful, (2 reviews)
"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.
#2 *Beautiful 1 BR Apartment - Central CT*
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

Find out more about Portland

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Portland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Portland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Portland. Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Portland short-term rentals, that won’t be hard to do.

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.