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Top Holiday Rentals in Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (68)
"Absolutely beautiful place to stay. "
The price is £354
includes taxes & fees
24 Aug - 25 Aug
The Weldon Hotel

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Studio Unit Walkable Everywhere

The price is £160
includes taxes & fees
4 Aug - 5 Aug
Studio Unit Walkable Everywhere

Private Entrance Residential Portland

8.0 out of 10, Very good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is £135
includes taxes & fees
30 Jul - 31 Jul
Private Entrance Residential Portland

In-town no frills 2 bedroom apt

7.6 out of 10, Good, (5)
The price is £156
includes taxes & fees
10 Aug - 11 Aug
In-town no frills 2 bedroom apt

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (106)
"Lovely place in the top floor of a multi property house. Everything you need in a cozy space. It is a walk up so pack up light. Clean, charming and comfy. Highly recommend. "
The price is £287
includes taxes & fees
12 Aug - 13 Aug
Adorable Portland getaway on the Eastern Promenade

East end. Walk to food, beer and downtown fun.

9.8 out of 10, Exceptional, (25)
"Great spot in Portland. Close to dozens of food options, breweries, and sites. Clean, comfortable, and spacious."
The price is £268
includes taxes & fees
26 Aug - 27 Aug
East end. Walk to food, beer and downtown fun.

Studio Apartment near downtown Walkable!

6.0 out of 10, (1)
"The listing said "Studio Apartment," but it is really just a bedroom with a bath. A mini-fridge, coffeemaker and microwave oven do not make this a "Studio" in the sense that I understand that word (i.e., a one-room apartment with kitchen and bath). When I went back and looked at the photos in the listing, that should have been obvious to me, but I got hung up on the word "Studio."That said, it was a comfortable room, although the bathroom was stingy on towels (no face cloths, only one hand...
The price is £145
includes taxes & fees
20 Aug - 21 Aug
Studio Apartment near downtown Walkable!

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is £433
includes taxes & fees
26 Aug - 27 Aug
Luxury on Back Cove - Three Gables

Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

10.0 out of 10, Exceptional, (47)
"This was a great property and even better host. We had a great time staying in downtown Portland. The apartment has great finishes. I will definitely plan to stay here again."
Private Rooftop Deck!/Artsy Apt/Old Port Arts Dist

Skyline 138: Charming West End Mansard Penthouse

9.2 out of 10, Wonderful, (17)
"Myself and a few friends stayed one night and the apartment was clean and comfortable and just what we needed."
The price is £554
includes taxes & fees
14 Aug - 15 Aug
Skyline 138: Charming West End Mansard Penthouse

Ocean view Victorian

9.8 out of 10, Exceptional, (91)
"Everything about the stay was fantastic. Great location and responsive host. "
Ocean view Victorian

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (111)
"While minutes away from the Old Port, our stay on Casco Bay allowed us to relax and unwind."
The price is £395
includes taxes & fees
13 Aug - 14 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty

Walkable near downtown 1 Bedroom

The price is £155
includes taxes & fees
18 Aug - 19 Aug
Walkable near downtown 1 Bedroom

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

8.8 out of 10, Excellent, (11)
"Great vacation rental!"
Beautiful, single story ranch. Next to city park with ocean view!

Charming Studio apartment with WiFi, AC in welcoming Portland

10.0 out of 10, Exceptional, (2)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is £176
includes taxes & fees
20 Aug - 21 Aug
Charming Studio apartment with WiFi, AC in welcoming Portland

Vintage Maine & Modern Convenience in Portlands Exclusive East End

9.8 out of 10, Exceptional, (44)
"Nikoline's home was a great home base for a fun weekend exploring downtown Portland. Super clean, well-furnished and in a great location just a short walk away from lots of cool restaurants and bars in Old Port.Nikoline was very friendly and responsive. Looking forward to going back and staying again for another Portland adventure."
Vintage Maine & Modern Convenience in Portlands Exclusive East End

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (5)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
Spacious Historic Home | 7BR West End for Groups

Charming Brownstone Downtown Free St|Perfect Getaway for 2

10.0 out of 10, Exceptional, (25)
"Great location, in the property manager was a huge help in excellent communicator"
Charming Brownstone Downtown Free St|Perfect Getaway for 2

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

10.0 out of 10, Exceptional, (14)
"We had a lovely weekend staying at this condo! It was clean, cozy, and the coffee bar was amazing! "
The price is £527
includes taxes & fees
3 Aug - 4 Aug
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
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

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Bayside Bowl, 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 great live music 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?

Cozy and Quiet Beautiful Home One Bedroom Private Bathroom in Portland Maine.: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and an electric kettle.

How many holiday rentals are there in Portland?

Choose from 144 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Bayside Bowl and Portland Observatory are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Portland Museum of Art. While here, Casco Bay Lines Ferry Terminal and Cross Insurance Arena 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.