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Holiday Rentals in Portland

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Holiday Rentals in Portland

Fun Downtown Location
9.8 out of 10, Exceptional, 49 reviews
"Nice space with 3 roomy bedrooms. Plenty of storage for clothes. Bathroom is small but not untypical of this era home. Steps to second floor are steep, so consider this. Kitchen has what you need for a short stay."
Fun Downtown Location
Charming 2 Bedroom Guest Apartment in Essex, CT
10.0 out of 10, Exceptional, 20 reviews
"The host had so many special touches to make this place a wonderful spot to stay. She had little snacks in the kitchen, with coffee and tea in the cupboard. There was half-and-half and the refrigerator, which we really appreciated. The towels in the bathroom were folded like you were in a special hotel. There was also lovely soap, shampoo and conditioner. Due to the cold temperature in the teens, she actually purchased some space heaters to make sure we were warm. Although there was a second...
Charming 2 Bedroom Guest Apartment in Essex, CT
Go Jump in the Lake!
10.0 out of 10, Exceptional, 127 reviews
"House was very clean, well equipped and had everything we needed to enjoy a relaxing getaway as a family. We enjoyed the firepit, covered porch and lakeside fun."
The price is €267
includes taxes & fees
12 Jun - 13 Jun
Go Jump in the Lake!
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Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, 15 reviews
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.6 out of 10, Exceptional, 25 reviews
"Joe was very attentive and left the house very clean for us. Definitely worth the money"
The price is €335
includes taxes & fees
6 Jun - 7 Jun
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, 2 reviews
"This was easily accessible to many places and the check-in process and communications with the owner were exceptional. Great place to stay."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, 106 reviews
"Very nice stay. Only disappointment was the lack of a hot tub. Otherwise a perfect venue for our group."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, 8 reviews
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is €358
includes taxes & fees
30 Jun - 1 Jul
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, 1 review
"Beautiful new home and property! Would one back for sure!"
The price is €802
includes taxes & fees
9 Jun - 10 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Massive 5 Bedrooms: 3King 2Queen
The price is €737
includes taxes & fees
5 Jun - 6 Jun
Massive 5 Bedrooms: 3King 2Queen
Amazing Lakefront Property
10.0 out of 10, Exceptional, 15 reviews
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, 7 reviews
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
lakefront estate
3.8 out of 10, 8 reviews
"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
comfortable home away from home
9.2 out of 10, Wonderful, 5 reviews
"This little house is tucked behind some bigger neighbors. It was comfortable and quiet! We had a ball watching the antics of a family of squirrels. It fit our needs perfectly!"
comfortable home away from home
Lakefront | King | W&D | Fire Pit | Kayaks | SUPs
9.8 out of 10, Exceptional, 14 reviews
"It a cute cottage style house that is steps away from a beach on the lake. Very close to the neighbors. If you play the record player you will cause a noise alarm to go off which I was not aware of prio to staying there."
The price is €440
includes taxes & fees
18 Jun - 19 Jun
Lakefront | King | W&D | Fire Pit | Kayaks | SUPs
The getaway! Located in the downtown area.
10.0 out of 10, Exceptional, 7 reviews
"This home was very nicely updated with new pillows, comfy bed and well stocked kitchen. Perfect location near the hospital"
The price is €279
includes taxes & fees
5 Jun - 6 Jun
The getaway! Located in the downtown area.
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
10.0 out of 10, Exceptional, 1 review
"This home was the perfect place for us to stay. It felt cozy and spacious at the same time. We had two couples, two kiddos and one single and had plenty of space to do our own things as well as cozy areas to just hang out and enjoy our time all together."
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, 7 reviews
"Quiet,peaceful,clean, friendly,cozy!!!!"
The price is €242
includes taxes & fees
17 Jun - 18 Jun
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access
9.0 out of 10, Wonderful, 15 reviews
"Our family stayed at this property while enjoying family weekend at UConn. The home was a nice distance between campus and fun activities. The house was clean and well stocked with amenities. We missed having a hot tub as was the reason we chose this home, but the views in the backyard were beautiful. We had a wonderful stay. Thank you!"
Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access
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See all available properties in Portland
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.

Other types of properties in Portland you may be interested in

Solano Inn
2.5 star property
7.6 out of 10, Good, 245 reviews
"The outside of the building is nothing like the inside. The room was great would stay there again for sure."
The price is €156
includes taxes & fees
5 Jul - 6 Jul
Solano Inn
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, 1,008 reviews
"Great "
The price is €150
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn Express Southington, an IHG Hotel
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very good, 1,005 reviews
"pleasant staff, convenient location and great free breakfast!"
The price is €107
includes taxes & fees
16 Jun - 17 Jun
Best Western Hartford Hotel & 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.

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as €242 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Connecticut River State Wildlife Area.

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.

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