Portland Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Portland vacation rentals

View from property

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, (154 reviews)
"I loved the location and the view!"
United States
Gabrielly
The price is ￥23,728
￥34,613 total
includes taxes & fees
Jun 1 - Jun 2
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Property grounds

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)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is ￥21,403
￥48,023 total
includes taxes & fees
Jun 2 - Jun 3
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is ￥27,093
￥57,593 total
includes taxes & fees
May 31 - Jun 1
#24 *Serenity* A Lakefront Cottage Retreat
Beach nearby

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 ￥22,422
￥49,354 total
includes taxes & fees
Jun 2 - Jun 3
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior

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 ￥24,333
￥51,871 total
includes taxes & fees
Jun 2 - Jun 3
Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (154 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 ￥26,276
￥53,508 total
includes taxes & fees
May 31 - Jun 1
Go Jump in the Lake!
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (2 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥19,110
￥25,162 total
includes taxes & fees
May 31 - Jun 1
Humble Abode #2
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"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 ￥13,761
￥19,011 total
includes taxes & fees
Jun 7 - Jun 8
Entire guest suite in South Windsor, Connecticut
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.6 out of 10, Exceptional, (37 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 ￥28,824
￥47,082 total
includes taxes & fees
Jun 10 - Jun 11
Walk To Goodspeed Opera House!
Property grounds

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 ￥22,932
￥49,622 total
includes taxes & fees
Jun 4 - Jun 5
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
1 bedroom, iron/ironing board, WiFi, bed sheets

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 ￥18,792
￥46,135 total
includes taxes & fees
Jun 1 - Jun 2
Once the old Schools house now a newly furnished Apartment
Fridge, microwave, stovetop, coffee/tea maker

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (13 reviews)
"Amazing stay. Easy check-in/access and Karl was quick to answer any questions I had. The place was immaculate, clean and modern with all the amenities you’ll need. Very convenient and walkable to coffee shops, bars & restaurants. We’ll be back."
United States
Todd L.
Charming Luxury 1BR Near Downtown. Dog Friendly!
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥18,792
￥46,135 total
includes taxes & fees
Jun 1 - Jun 2
All New 1BR with tons of Charm
Interior

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

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (10 reviews)
"Place is nice would stay again "
United States
nic
The price is ￥24,012
￥68,709 total
includes taxes & fees
Jun 1 - Jun 2
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Interior

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Host had great communication. The unit was clean, cozy and comfortable. Will book again when in the area."
United States
Tod B.
The price is ￥10,988
￥39,929 total
includes taxes & fees
Jun 7 - Jun 8
The Sun Filled Cozy Creamery
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is ￥16,244
￥41,087 total
includes taxes & fees
Jun 1 - Jun 2
2BR Apartment Near Wesleyan 102
Interior

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Windham
10.0 out of 10, Exceptional, (15 reviews)
"All and all a great place to stay."
United States
Anonymous traveler
The price is ￥35,831
￥108,091 total
includes taxes & fees
Jun 15 - Jun 16
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
9.8 out of 10, Exceptional, (10 reviews)
"Great place"
United States
John S.
The price is ￥20,543
￥45,282 total
includes taxes & fees
May 31 - Jun 1
Modern & Cozy Cape | 4 Bedroom House | Central Location
TV, offices

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 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 ￥15,479
￥40,414 total
includes taxes & fees
May 31 - Jun 1
Private Apartment in Berlin
Smart TV

#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is ￥27,945
￥60,005 total
includes taxes & fees
Jun 3 - Jun 4
#23 *COMFORT & LUXURY* 3 BR/2 BA House
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

Economy Inn

Economy Inn

10/10 Excellent
"Nice"
Donald 1-night trip
Posted 2 hours ago
Economy Inn

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:

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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?

Downtown and secluded: This vacation home rental outside of Portland offers a balcony, a selection of books, 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 fridge, and a stovetop, 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.