A river with a large bridge and a small boat on the shore.

Portland Vacation Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

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
2.5 star property
East Haddam
9.6 out of 10, Exceptional, (163 reviews)
"Great stay! "
United States
Tanitra
The price is SAR 541
SAR 795 total
includes taxes & fees
6 Aug - 7 Aug
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, (52 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is SAR 717
SAR 1,365 total
includes taxes & fees
21 Jul - 22 Jul
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.2 out of 10, Wonderful, (45 reviews)
"The property was clean and accommodating."
United States
Ann Marie T.
The price is SAR 508
SAR 1,136 total
includes taxes & fees
9 Jul - 10 Jul
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, (41 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 SAR 999
SAR 1,769 total
includes taxes & fees
5 Aug - 6 Aug
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Property grounds

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 SAR 451
SAR 593 total
includes taxes & fees
9 Jul - 10 Jul
Humble Abode #2
Exterior

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 SAR 443
SAR 1,096 total
includes taxes & fees
8 Jul - 9 Jul
All New 1BR with tons of Charm
A lakeside setting with a row of colorful kayaks and a sailboat docked.

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 SAR 770
SAR 1,457 total
includes taxes & fees
26 Jul - 27 Jul
Go Jump in the Lake!
Smart TV

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 SAR 487
SAR 815 total
includes taxes & fees
8 Jul - 9 Jul
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Smart TV, fireplace, books, music library

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)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is SAR 567
SAR 1,081 total
includes taxes & fees
15 Jul - 16 Jul
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Interior

Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester

Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (13 reviews)
"Great place"
United States
Jason
The price is SAR 526
SAR 871 total
includes taxes & fees
12 Jul - 13 Jul
Peaceful pet friendly 1-bedroom with in unit laundry in enjoyable Manchester
Smart TV, offices

Premier League Pad - with Free Parking, Heat & AC

Premier League Pad - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (3 reviews)
"Perfect place to stay if you need to stay in Manchester. The apartment was so clean and accommodating. The host was very easy to communicate with! I would gladly stay here again!"
United States
Corey J.
The price is SAR 423
SAR 915 total
includes taxes & fees
19 Jul - 20 Jul
Premier League Pad - with Free Parking, Heat & AC
Smart TV, books

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
9.8 out of 10, Exceptional, (6 reviews)
The price is SAR 575
SAR 1,080 total
includes taxes & fees
8 Jul - 9 Jul
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (38 reviews)
"Needed a one night stay - worked fine"
United States
Michelle B.
The price is SAR 668
SAR 1,090 total
includes taxes & fees
15 Jul - 16 Jul
Walk To Goodspeed Opera House!
TV

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
10.0 out of 10, Exceptional, (1 review)
"Clean & Comfortable, excellent accessibility to area restaurants & shopping.There was a hitch with my payment before check-in, the owner was helpful & communicative in resolving the issue.Overall, a great place to stay."
United States
Thomas S.
The price is SAR 443
SAR 1,096 total
includes taxes & fees
8 Jul - 9 Jul
All new 1BR apartment with all the features you are looking for
Smart TV

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 SAR 324
SAR 448 total
includes taxes & fees
13 Jul - 14 Jul
Entire guest suite in South Windsor, Connecticut
Smart TV, offices, computer monitors

TruStay in Central CT

TruStay in Central CT
Manchester
The price is SAR 415
SAR 882 total
includes taxes & fees
4 Aug - 5 Aug
TruStay in Central CT
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, (17 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is SAR 646
SAR 1,291 total
includes taxes & fees
3 Aug - 4 Aug
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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, (15 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.
The price is SAR 338
SAR 1,272 total
includes taxes & fees
8 Jul - 9 Jul
Charming Luxury 1BR Near Downtown. Dog Friendly!
Interior

The Historic Hideaway

The Historic Hideaway
Avon
6.0 out of 10, (4 reviews)
"Once we found the house it was very warm & cozy. The mini- muffins on the counter was a bonus. House mailbox was 87 but address was 89 that you only see if door is closed which it wasn't on 1st 2 passes. Limited exterior lights made coming back at night a challenge. "
United States
Kim C.
The price is SAR 282
SAR 1,014 total
includes taxes & fees
13 Jul - 14 Jul
The Historic Hideaway
Property grounds

Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen

Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
Manchester Center
10.0 out of 10, Exceptional, (9 reviews)
"Nice private place to stay."
United States
Brian A.
The price is SAR 488
SAR 637 total
includes taxes & fees
8 Jul - 9 Jul
Cozy 1-bedroom apartment in enchanting Manchester, with A/C & wifi, kitchen
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

The Capitol Hotel

The Capitol Hotel

8/10 Good
"Good"
Marjorie 1-night trip
Posted 1 hour ago
The Capitol Hotel

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?

NEW Coastal Cottage 2 Miles to Beach + Lake Access: This vacation home rental outside of Portland is equipped with a barbecue grill, 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 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.