Holiday Rentals in Portland

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Our top choices for Portland holiday rentals

9.6 out of 10, Exceptional, (121 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is €145
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
9.8 out of 10, Exceptional, (36 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 €240
includes taxes & fees
4 Mar - 5 Mar
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
10.0 out of 10, Exceptional, (7 reviews)
"Place is nice would stay again "
United States
nic
The price is €333
includes taxes & fees
4 Mar - 5 Mar
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is €219
includes taxes & fees
9 Mar - 10 Mar
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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 €257
includes taxes & fees
4 Mar - 5 Mar
Once the old Schools house now a newly furnished Apartment

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is €257
includes taxes & fees
4 Mar - 5 Mar
All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"All and all a great place to stay."
United States
Anonymous traveller
The price is €434
includes taxes & fees
10 Mar - 11 Mar
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
9.6 out of 10, Exceptional, (19 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is €240
includes taxes & fees
4 Mar - 5 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
9.2 out of 10, Wonderful, (40 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is €300
includes taxes & fees
1 Apr - 2 Apr
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.8 out of 10, Exceptional, (8 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 €290
includes taxes & fees
9 Mar - 10 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House
10.0 out of 10, Exceptional, (7 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is €172
includes taxes & fees
8 Mar - 9 Mar
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
10.0 out of 10, Exceptional, (5 reviews)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is €242
includes taxes & fees
4 Mar - 5 Mar
Modern & Cozy Cape | 4 Bedroom House | Central Location

Apartment in Manchester Center

Humble Abode #2
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is €138
includes taxes & fees
5 Mar - 6 Mar
Humble Abode #2

Apartment in East Haddam

Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (34 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 €268
includes taxes & fees
4 Mar - 5 Mar
Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (16 reviews)
"Great Location - all the amenities you need for a nice restful stay. Did not have to reach-out to the host at all during our stay. "
United States
Robert S.
The price is €185
includes taxes & fees
24 Mar - 25 Mar
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (6 reviews)
"Great location. Clean property"
United States
Sue R.
The price is €197
includes taxes & fees
23 Mar - 24 Mar
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is €703
includes taxes & fees
4 Mar - 5 Mar
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is €184
includes taxes & fees
8 Mar - 9 Mar
Cozy Guest Suite in Historic Home
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 €105
includes taxes & fees
11 Mar - 12 Mar
Entire guest suite in South Windsor, Connecticut
9.2 out of 10, Wonderful, (11 reviews)
"Very clean and super comfortable. Would stay here again."
United States
vanessa c.
The price is €239
includes taxes & fees
8 Mar - 9 Mar
Cozy Nest ~ 3.5BR & 2Bath Home ~ Manchester CT
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

Find out more about Portland

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 €145 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?

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford: This holiday home rental outside of Portland has air conditioning and laundry facilities 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 that 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 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.