Holiday Homes in Portland

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Featured Holiday Homes in Portland

Spacious 4-bedroom house located in the heart of Portland, ME.

10.0 out of 10, Exceptional, (1)
"Clean, comfortable. "
The price is AU$1,397
includes taxes & fees
17 Sept - 18 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.

Modern Getaway by the Sea

The price is AU$914
includes taxes & fees
25 Aug - 26 Aug
Modern Getaway by the Sea

Luxurious Penthouse with Modern Design in Downtown

9.8 out of 10, Exceptional, (12)
"Just as advertised, would definitely stay here again. Great location!"
Luxurious Penthouse with Modern Design in Downtown

5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

10.0 out of 10, Exceptional, (144)
"This was our second stay at Beth’s home, and it certainly won’t be the last (as long as she’s willing to have us!) Everything is absolutely perfect. Beth is a thoughtful host, the location is perfect and the home is beautiful - you can’t go wrong!"
5 Star Back Cove Hide-Away 1 bedroom Back Cove apartment with water views!

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

Convenient Portland home 3 miles from Downtown

10.0 out of 10, Exceptional, (32)
"The home was in a great neighborhood and the place was very clean. My family and I enjoyed staying here."
Convenient Portland home 3 miles from Downtown

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (56)
"Quiet neighborhood. Nice place"
The price is AU$463
includes taxes & fees
14 Sept - 15 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

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.

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 AU$2,621
includes taxes & fees
24 Aug - 25 Aug
Spacious Historic Home | 7BR West End for Groups

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

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

10.0 out of 10, Exceptional, (61)
"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 AU$2,045
includes taxes & fees
2 Sept - 3 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Portland Home: Walk Downtown!

10.0 out of 10, Exceptional, (23)
"Absolutely loved our stay here. The home is bright, spacious, comfortable, and beautiful. Jen was such a wonderful host - helpful and accessible for anything we needed. Looking forward to staying here again!"
Spacious Portland Home: Walk Downtown!

Entire House Deering Highlands

9.4 out of 10, Exceptional, (6)
"Enjoyed our stay. Good communication with owners. House was clean and in a good location. Short drive to downtown and grocery stores."
Entire House Deering Highlands

Rent a room in the gorgeous Holt House

8.4 out of 10, Very good, (19)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House

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

9.0 out of 10, Wonderful, (14)
"Great vacation rental!"
Beautiful, single story ranch. Next to city park with ocean view!

Art Filled East End Home a short walk to waterfront, restaurants and shops

9.8 out of 10, Exceptional, (28)
"Gorgeous property, responsive host, excellent location! All around a great experience. We would not hesitate to stay here again."
Art Filled East End Home a short walk to waterfront, restaurants and shops

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

9.4 out of 10, Exceptional, (3)
"Really nice place. Beds are comfortable. Had nice hot tub with propane fire. Lovely back patio. "
The price is AU$1,101
includes taxes & fees
8 Sept - 9 Sept
Coastal Escape | Hot Tub Fire Pit Chef Kitchen

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (81)
"Perfect location to take advantage of all the foodie places!! Place was clean and hosts were wonderful. "
The Globe House on Munjoy Hill - Walk to Breweries

Sunny Modern Oasis in Portland’s Trendy East End

10.0 out of 10, Exceptional, (53)
"We truly enjoyed our stay at Sunny Modern Oasis. The Munjoy Hill area is spectacular. The apartment is modern and extremely well-equipped. Kitchen was great. Mark was responsive and very helpful. We had a wonderful time in Portland and would stay here again if we return. "
Sunny Modern Oasis in Portland’s Trendy East End

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (29)
"Perfect stay for a quick trip to Portland! "
Modern & Sunny House Steps from the Promenade. Private Parking!
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