Photo by Rick Bucchino

Portland Holiday Rentals

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Holiday Rentals in Portland

136 Raymond · Prime West Hartford Center Location: Historic Gem

10.0 out of 10, Exceptional, (20)
"Immaculate Victorian home wonderfully renovated for modern convenience. Perfect Location; easy on/off Interstate 84. Gracious host who was ultra responsive. Very pleasant stay. "
136 Raymond · Prime West Hartford Center Location: Historic Gem

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!

Spacious 5-bedroom vacation home just 5 minutes drive to Connecticut River

10.0 out of 10, Exceptional, (31)
"We stayed for our annual Columbus Day weekend away with a group of 9 friends. The house was very comfortable and we had plenty of space. We really enjoyed the game room in the evenings - all the games were in excellent condition and everything was in working order (which has not usually been the case at other vacation rentals we have been to). We were lucky enough to have beatiful fall weather all weekend, so we could enjoy the lovely back yard. We made use of the gas grill, watch a playoff game...
Spacious 5-bedroom vacation home just 5 minutes drive to Connecticut River

Go Jump in the Lake!

10.0 out of 10, Exceptional, (137)
"We like this place a lot. House was clean and Todd was very responsive to my questions. There are two bedrooms with one on the second floor. One thing we didn’t realize was, to get to the second floor there is a spiral staircase. "
Go Jump in the Lake!

Historic Essex Home w/ Large Yard Near Downtown!

9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!

Island Vibes Home

10.0 out of 10, Exceptional, (8)
"Such a perfect space for us. Home was spotless! We had a wedding in Hartford, three bedrooms worked out perfectly two bathrooms everyone had plenty of space. Beautiful kitchen and amenities. We would stay here again in a heartbeat. Wish we could’ve stayed longer"
Island Vibes Home

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

9.0 out of 10, Wonderful, (36)
"Wonderful host. Very thoughtful - lots provided in the house that you need to have a great stay. "
The price is AU$433
includes taxes & fees
2 Dec - 3 Dec
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.8 out of 10, Exceptional, (9)
"It was a very comfortable house! We were only there 2 days for the Mizzou game. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (47)
"What a gem this cute house was on the lake! The owners didn’t skip a beat with the attention to detail. It had everything and was so clean. Communication was spot on. We will definitely book again the next time we come to CT! We already miss waking up with coffee and watching the sun come up over the lake. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Fun Downtown Location 2nd flr

9.8 out of 10, Exceptional, (65)
"This property is a remodeled older house. With all that old house charm. It is spacious and has three bedrooms, each with a queen bed. The couch is extremely comfortable and it was great watching TV and sipping wine."
Fun Downtown Location 2nd flr

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

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Exquisite Downtown Loft Apartment

8.0 out of 10, Very good, (6)
"Will stay again"
Exquisite Downtown Loft Apartment

#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*

10.0 out of 10, Exceptional, (2)
"The upstairs kitchen may need some extra ceramic bowls and silverware. The hot water may need to be turned up, it was tepid at best. Jeff was more than helpful getting us situated and comfortable. Great neighborhood, and availability to groceries, restaurants, and the great brewery 2 minutes away. Great room for families for togetherness and privacy"
#11 -* 4 Bedrooms, 3 Baths! Sleeps up to 13!*

The Lake House

9.8 out of 10, Exceptional, (8)
"Wonderful place to camp for a large family, particularly in summertime. Great view of the lake and the best sunsets. "
The Lake House

Lake Getaway at Coventry Lake! close to Uconn

10.0 out of 10, Exceptional, (13)
"Nice spot, close to campus and perfect size."
Lake Getaway at Coventry Lake! close to Uconn

Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access

9.0 out of 10, Wonderful, (21)
"This was an adult weekend away with our dog, outdoor weekend planned with several hikes. We wanted a change of scenery and a break from the norm. Very nice home, lots of space. Great kitchen. The 2 Alexas talking were a lot for me (one wasn’t working and she was very vocal about that). I’m old school when it’s comes to turning on lights. Welcome book is great. The location is on and near a very busy street, which was only a concern because of the dog. The yard. We are fanatics with...
Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is AU$179
includes taxes & fees
26 Nov - 27 Nov
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

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

9.6 out of 10, Exceptional, (28)
"The property was exactly like stated on VERBO. Cozy with all amenities you could need. "
The price is AU$442
includes taxes & fees
2 Dec - 3 Dec
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks

lakefront estate

3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

9.4 out of 10, Exceptional, (6)
"There was 7 family members all had sleeping quarters. We enjoyed the location. The lake was beautiful went out on kayaks and enjoyed walks around the neighborhood. Sat outside and played games and enjoyed the fire. Nice weekend was had by all "
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
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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Other types of properties in Portland you may be interested in

Solano Inn

2.5 star property
8.8 out of 10, Excellent, (71)
"Wonderful staff, spacious room, quiet setting, huge TV, very clean. "
The price is AU$167
includes taxes & fees
26 Nov - 27 Nov
Solano Inn

The Capitol Hotel, Ascend Hotel Collection

3.0 star property
7.4 out of 10, Good, (943)
"Didn’t enjoy the fact that they charged $15 for parking."
The price is AU$133
includes taxes & fees
22 Dec - 23 Dec
The Capitol Hotel, Ascend Hotel Collection

Holiday Inn Express Southington, an IHG Hotel

2.5 star property
8.6 out of 10, Excellent, (1077)
"Nice place to rest your head, breakfast was lackluster, convenient location."
The price is AU$204
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Southington, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This holiday home rental outside of Portland has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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. In the wider area, you’ll find Arrigoni Winery and Wesleyan University.

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.