Photo by Rick Bucchino

Portland Holiday Rentals

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Holiday Rentals in Portland

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (3)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is AU$184
includes taxes & fees
3 Feb - 4 Feb
Postcard Cabins Machimoodus

COZY Maple Tree Cabin - Romantic or family getaway. Private - Warm and Cozy!

10.0 out of 10, Exceptional, (26)
"We were in awe of how cool this cabin is, everyone kept saying, “ It’s like a Hallmark Christmas movie”. It couldn’t have been more perfect for our family. The 8yr old twin boys loved the air hockey table and it was great having that space upstairs for them to enjoy movies and games too. We had a great Christmas dinner and had all the amenities, perfect amount of seating. We tried s’mores at the fire pit, but made them quickly and ran in because it was 15 but we still got in another great...
The price is AU$1,043
includes taxes & fees
1 Feb - 2 Feb
COZY Maple Tree Cabin - Romantic or family getaway. Private - Warm and Cozy!

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

9.2 out of 10, Wonderful, (12)
"Our visit at this VRBO was almost excellent… the only issue we had was with theTVs. We could not get the TVs in the bedroom to work. Cleanliness was exceptional! Availability of food/meal supplies was great. It was nice that there was ice already made for us. The towel and wash cloths were fluffy and absorbent. The queen bed and pillows were very comfortable. We cannot say there was anything that did not meet expectations! Anyone would be comfortable there. We would book again. "
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (8)
"Well priced and centrally located in the town. Host was very respectful and helpful. Would definitely book again if I visit southington again."
NEW-Another Fun Downtown Location 1st floor

Charming Cottage by the Lake♥️

9.6 out of 10, Exceptional, (8)
"Very cozy little home. "
Charming Cottage by the Lake♥️

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is AU$1,382
includes taxes & fees
1 Feb - 2 Feb
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Island Vibes Home

9.8 out of 10, Exceptional, (13)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home

NEW 5Bed Close to Bloomfield Center & Golf Courses

2.0 star property
10.0 out of 10, Exceptional, (2)
"Omg i dont even know where to start but this property was phenomenal love it i would recommend a million times are more all im ask since this a newly released property plz take care of it like i did so otheres can have our experience clean after ur self if u can but quite spacious parking great nth to worry about 3 to 5 mins from most convenient places "
The price is AU$1,076
includes taxes & fees
6 Feb - 7 Feb
NEW 5Bed Close to Bloomfield Center & Golf Courses

Totally Private Cozy studio in awesome Hartford with WiFi, AC

The price is AU$317
includes taxes & fees
3 Feb - 4 Feb
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is AU$631
includes taxes & fees
4 Feb - 5 Feb
Blue Back Bungalow

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

10.0 out of 10, Exceptional, (33)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

Storybook Cottage

10.0 out of 10, Exceptional, (1)
"Very charming property, accurate description per listing. Very clean and overall a great stay."
Storybook Cottage

Cozy BoHo pet & family friendly near downtown & hospitals

8.4 out of 10, Very good, (7)
"We stayed 4 nights for our family trip. The home was sparkling clean and we found all we need. I love boho styled rooms. No issues with neighbors. All kind of TV subscription available. Overall very positive experience. Thank you!"
The price is AU$451
includes taxes & fees
4 Feb - 5 Feb
Cozy BoHo pet & family friendly near downtown & hospitals

Go Jump in the Lake!

10.0 out of 10, Exceptional, (138)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
A “Wow” Experience everywhere there is something to stimulate your mind Interest

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

9.6 out of 10, Exceptional, (7)
"This property was exactly what we needed. Perfect location beautiful house very clean and very comfortable. We will definitely return "
The price is AU$528
includes taxes & fees
19 Feb - 20 Feb
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (8)
"Very classy, unique, well taken care of home. I would highly recommend this for anyone."
Charming Farmhouse w/ Pool & Fishing Pond!

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!

Lux Boutique Large Private LOFT Pratt St Hartford

9.0 out of 10, Wonderful, (10)
"The space was clean and accuratly described. Would stay here again for the central location in the city and for the value. Thanks"
The price is AU$301
includes taxes & fees
2 Feb - 3 Feb
Lux Boutique Large Private LOFT Pratt St Hartford
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
9.4 out of 10, Exceptional, (86)
"Diamond in the rough! The rooms are absolutely gorgeous and the staff is incredibly friendly and kind! "
The price is AU$200
includes taxes & fees
6 Feb - 7 Feb
Solano Inn

Holiday Inn Express Southington, an IHG Hotel

2.5 star property
8.8 out of 10, Excellent, (1008)
"Its great"
The price is AU$203
includes taxes & fees
9 Feb - 10 Feb
Holiday Inn Express Southington, an IHG Hotel

The Farmington Inn & Suites

3.0 star property
8.8 out of 10, Excellent, (1003)
"I needed to check in quickly to make an online meeting and the speedy staff got me processed immediately. This is a lovely hotel and the staff works hard to make sure the guests are comfortable. "
The price is AU$210
includes taxes & fees
3 Feb - 4 Feb
The Farmington Inn & Suites
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.

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. 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.