Portland Holiday Rentals

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Holiday Rentals in Portland

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is NZ$486
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

Studio Unit Walkable Everywhere

West Bayside
5.8 out of 10, (6)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
United States
Anonymous traveller
The price is NZ$246
includes taxes & fees
17 Nov - 18 Nov
Studio Unit Walkable Everywhere

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very good, (15)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is NZ$265
includes taxes & fees
16 Nov - 17 Nov
In-town no frills 2 bedroom apt

Private Entrance Residential Portland

Deering Center
9.2 out of 10, Wonderful, (5)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
Private Entrance Residential Portland

Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Downtown Portland
9.8 out of 10, Exceptional, (20)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Knock on Wood | Airy Charm in Heart of Downtown

Parkside
8.8 out of 10, Excellent, (25)
"stayed for one night to celebrate prom, it was a great central location, parking was a bit difficult to find though. Also the sheets were wet, not sure if the humidifier was broken. Overall good stay! would book again"
United States
Sabrina C.
The price is NZ$579
includes taxes & fees
9 Dec - 10 Dec
Knock on Wood | Airy Charm in Heart of Downtown

Beautiful, single story ranch. Next to city park with ocean view!

Back Cove
9.2 out of 10, Wonderful, (19)
"We had a wonderful stay with friends! Ken was very accommodating to all of our needs!"
United States
Ryan D.
Beautiful, single story ranch. Next to city park with ocean view!

Back yard paradise

Portland
9.8 out of 10, Exceptional, (22)
"I live in California, but my son was married in Portland (our home state). We spent a long weekend close to family and wedding activities. This is a comfortable home, in a great location. I feel fortunate to have chosen the perfect VRBO."
United States
Tracey C.
Back yard paradise

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is NZ$334
includes taxes & fees
4 Dec - 5 Dec
Adorable Portland getaway on the Eastern Promenade

City Amenities, Casco Bay Sunrises and Natural Beauty

East Deering
9.8 out of 10, Exceptional, (122)
"Plenty of room for everyone, good well equipped kitchen, great location on the bay. Would recommend to others to stay here."
United States
Robin P.
City Amenities, Casco Bay Sunrises and Natural Beauty

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering
10.0 out of 10, Exceptional, (64)
"We stayed for a group trip to Portland and this was the perfect spot. Location is fantastic, lots of comfortable sleeping options, and great communication from the host. Highly recommend! "
United States
Kaitie H.
The price is NZ$1,902
includes taxes & fees
17 Nov - 18 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Cozy, Elegant and Bright 2 bed in the East End

Munjoy Hill
9.8 out of 10, Exceptional, (52)
"Great location"
United States
Allen S.
Cozy, Elegant and Bright 2 bed in the East End

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Quintessential Maine Beach Cottage

Goose Rocks Beach
10.0 out of 10, Exceptional, (137)
"Incredible stay in Maine with our dog. Everything was perfect!!!!"
United States
David Y.
Quintessential Maine Beach Cottage

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Old Orchard Beach
9.8 out of 10, Exceptional, (45)
"😍😍😍"
United States
Sara L.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Old Orchard Beach
9.6 out of 10, Exceptional, (67)
"Made a great place for a business retreat. WiFi worked well and we had plenty of space to spread out."
United States
dan b.
The price is NZ$2,189
includes taxes & fees
17 Nov - 18 Nov
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Sebago Lake Cottage on Raymond Cape

Raymond
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape

The Moonglow! A beautiful ocean view house in Biddeford!

Biddeford
9.8 out of 10, Exceptional, (124)
"House was beautiful! Comfy beds, amazing views,great location!"
United States
Katherine C.
The Moonglow! A beautiful ocean view house in Biddeford!

Historic Kennebunkport home only 0.3 miles to Dock Square

Kennebunkport
10.0 out of 10, Exceptional, (75)
"Wonderful home close to downtown. Comfortable house and great host!"
United States
Kyle B.
The price is NZ$900
includes taxes & fees
17 Nov - 18 Nov
Historic Kennebunkport home only 0.3 miles to Dock Square

Private Lakefront Estate with 180 Degree Views

Raymond
10.0 out of 10, Exceptional, (7)
"This was a fabulous property in perfect location. The house and grounds were amazing. It was a sensational week."
United States
Brian C.
Private Lakefront Estate with 180 Degree Views
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, 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 NZ$246 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

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Maine Narrow Gauge Railroad Company and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Portland speak highly of the bustling port and array of shops. The fascinating museums and acclaimed theatre scene are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Portland has to offer?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Portland is located on the beach, and has a patio, a garden and a BBQ to put you at ease 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Portland?

Choose from 87 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Maine Narrow Gauge Railroad Company and Museum and Bayside Bowl are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Wadsworth-Longfellow House. While here, Fore Street Gallery and Casco Bay Lines Ferry Terminal are other places worth a visit.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for small groups.