Portland Holiday Rentals

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Holiday Rentals in Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (69)
"Absolutely beautiful place to stay. "
The price is NZ$810
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.

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (2)
"This apartment is great- the furnishings are cute and the bed is comfy. It has a kitchen with all of the cookware I needed, and off-street parking is awesome. I liked that it was really convenient to downtown, but outside of the busy, touristy parts of town. The owners were communicative, but not intrusive. It was overall a great experience. I would definitely stay here again."
The price is NZ$342
includes taxes & fees
18 Aug - 19 Aug
Private Entrance Residential Portland

Studio Unit Walkable Everywhere

6.0 out of 10, (1)
"Before check in the host was kind and incredibly communicative. Upon check out they asked how our stay was and I wrote them a message saying I’d rather discuss this before leaving a bad review but they left me on read… When we arrived there were so many unhoused folx outside the apt we didn’t feel safe entering. we literally saw a woman being chased/harassed while we were pulling up. If I wasn’t with my partner I would’ve had to cancel due to feeling unsafe. I have no bad feelings about unhoused...
The price is NZ$352
includes taxes & fees
24 Aug - 25 Aug
Studio Unit Walkable Everywhere

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (109)
"Unit was very clean"
The price is NZ$529
includes taxes & fees
7 Sept - 8 Sept
Adorable Portland getaway on the Eastern Promenade

Walkable near downtown 1 Bedroom

The price is NZ$343
includes taxes & fees
10 Sept - 11 Sept
Walkable near downtown 1 Bedroom

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

Elegant and efficient Island home 4 miles from downtown Portland

8.0 out of 10, Very good, (1)
"Historic and charming home in a most interesting setting-- the community was a former military fort and barracks. Chat with neighbors on the front porch or watch wildlife and hang out in the backyard picnic tables. Comfortable beds and two full baths makes it good for group of 4-6 people. The golf cart is a godsend but there are bicycles and kayaks for land and water exploration. We didn't make it to the lovely looking pool or rec center for gym/bowling but they look like lots of fun. Rental and...
Elegant and efficient Island home 4 miles from downtown Portland

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 NZ$352
includes taxes & fees
7 Sept - 8 Sept
Studio Apartment near downtown Walkable!

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (112)
"While minutes away from the Old Port, our stay on Casco Bay allowed us to relax and unwind."
The price is NZ$675
includes taxes & fees
20 Aug - 21 Aug
City Amenities, Casco Bay Sunrises and Natural Beauty

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...
The price is NZ$2,820
includes taxes & fees
24 Aug - 25 Aug
Spacious Historic Home | 7BR West End for Groups

Knock on Wood | Airy Charm in Heart of Downtown

9.0 out of 10, Wonderful, (19)
"This apartment is so well situated to walk to parks, restaurants and shopping. It’s a very large space and quite comfortable. "
The price is NZ$823
includes taxes & fees
8 Sept - 9 Sept
Knock on Wood | Airy Charm in Heart of Downtown

Island View House BnB Self Check-In # 4 / Free Off-Street Parking

10.0 out of 10, Exceptional, (9)
"This was the perfect spot to stay for me and my husband! We were able to walk everywhere we wanted while avoiding staying in the more touristy areas. We felt like locals and we would definitely stay here again! "
The price is NZ$779
includes taxes & fees
20 Aug - 21 Aug
Island View House BnB Self Check-In # 4 / Free Off-Street Parking

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

9.0 out of 10, Wonderful, (13)
"Great vacation rental!"
Beautiful, single story ranch. Next to city park with ocean view!

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is NZ$1,103
includes taxes & fees
24 Aug - 25 Aug
Luxury on Back Cove - Three Gables

Charming Brownstone Downtown Free St|Perfect Getaway for 2

10.0 out of 10, Exceptional, (27)
"It is a beautiful apartment across the street from the art museum. "
Charming Brownstone Downtown Free St|Perfect Getaway for 2

Back yard paradise

9.8 out of 10, Exceptional, (20)
"We had a wonderful weekend with family at this nicely appointed space that is close to downtown Portland. We all enjoyed swimming in the pool and hanging out on the deck."
Back yard paradise

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is NZ$723
includes taxes & fees
17 Aug - 18 Aug
Elegant condo - walk to Portland's best restaurants & Old Port

Ocean view Victorian

9.8 out of 10, Exceptional, (92)
"Everything about the stay was fantastic. Great location and responsive host. "
Ocean view Victorian

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

10.0 out of 10, Exceptional, (60)
"Very clean, lots of room for gathering. Perfect location on a quiet street with great views of the lake. Plenty of towels, bedding, water, etc. Would come back!"
The price is NZ$2,184
includes taxes & fees
25 Aug - 26 Aug
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
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 fascinating museums 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 Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and free WiFi 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 123 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, 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.