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Holiday Homes in Portland

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Portland holiday homes

Interior

1. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AU$545
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Outdoor dining

2. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is AU$825
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
Exterior

3. The 87th Townhome - Local Landmark

The 87th Townhome - Local Landmark
West End
9.4 out of 10, Exceptional, (9 reviews)
"We had a wonderful time at the property! Super close walking distance to great shopping and restaurants. Host was so responsive and even checked in to make sure we were having a great stay. Would stay again!"
United States
Amy B.
The price is AU$947
includes taxes & fees
8 Sept - 9 Sept
The 87th Townhome - Local Landmark
Outdoor dining

4. Spacious Portland Home + Parking

Spacious Portland Home + Parking
Parkside
8.6 out of 10, Excellent, (4 reviews)
"we used the house has home base for several outings in Portland. Great location and easy parking."
United States
Ellen M.
The price is AU$1,033
includes taxes & fees
10 Sept - 11 Sept
Spacious Portland Home + Parking
Outdoor dining

5. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Overall amazing experience! Property is beautifully maintained. Perfectly located, within walking distance from bakeries, pubs, and restraunts. Host was responsive and helpful."
United States
Jacqui B.
The price is AU$815
includes taxes & fees
9 Sept - 10 Sept
Modern & Sunny House Steps from the Promenade.
Exterior

6. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
The price is AU$988
includes taxes & fees
14 Sept - 15 Sept
Willard Square Family Home
Interior

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

Spacious 4-bedroom house located in the heart of Portland, ME.
Munjoy Hill
10.0 out of 10, Exceptional, (18 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is AU$1,402
includes taxes & fees
9 Sept - 10 Sept
Spacious 4-bedroom house located in the heart of Portland, ME.
Interior

8. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Oakdale
10.0 out of 10, Exceptional, (1 review)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
United States
Andy W.
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Exterior detail

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

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is AU$1,816
includes taxes & fees
30 Sept - 1 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Living area

10. Two Beautiful apartment

Two Beautiful apartment
Back Cove
10.0 out of 10, Exceptional, (29 reviews)
"Such an amazing property and host in an incredible location! "
United States
Devin M.
Two Beautiful apartment
Living area

11. Charming Historic Estate | In-town location

Charming Historic Estate | In-town location
West End
10.0 out of 10, Exceptional, (2 reviews)
"Steve was wonderful and readily available for any of our questions or just helpful recommendations! Made our stay so much more pleasurable!! We enjoyed 3 meals by their on staff chef. She also did an amazing job. We travel with 17 so needless to say it’s a lot but we had more than enough space for everyone. Also, have to mention the outdoor space was delightful!"
United States
shelley w.
Charming Historic Estate | In-town location
Property grounds

12. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (29 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
The price is AU$414
includes taxes & fees
7 Sept - 8 Sept
Serenity between the lakes and seashore
Interior

13. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AU$454
includes taxes & fees
8 Sept - 9 Sept
Tranquility between the Lakes & Sea
Living area

14. Huge New Townhome 10mins from the Beach

Huge New Townhome 10mins from the Beach
Saco
9.0 out of 10, Wonderful, (2 reviews)
"The location was very convenient. Easy drive to downtown Saco and Biddeford. As well as very quick access to the highway so Portland and other points are easy to get to. Ample parking."
United States
Ellen L.
The price is AU$756
includes taxes & fees
7 Sept - 8 Sept
Huge New Townhome 10mins from the Beach
Living area

15. Walk to Beach | Patio | Full Kitchen | Parking

Walk to Beach | Patio | Full Kitchen | Parking
Old Orchard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property, would stay again!"
United States
Jason N.
The price is AU$825
includes taxes & fees
7 Sept - 8 Sept
Walk to Beach | Patio | Full Kitchen | Parking
Living area

16. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
10.0 out of 10, Exceptional, (2 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is AU$1,017
includes taxes & fees
30 Sept - 1 Oct
Windham Lakefront: Fire Pit and Modern Comforts
Private kitchen

17. Quiet Spot in Lovely Freeport Neighborhood

Quiet Spot in Lovely Freeport Neighborhood
Freeport
The price is AU$601
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in Lovely Freeport Neighborhood
Private kitchen

18. The Links Lodge - Modern Golf and Beach Retreat

The Links Lodge - Modern Golf and Beach Retreat
Old Orchard Beach
10.0 out of 10, Exceptional, (13 reviews)
"Great place! Perfectly clean, would recommend!"
United States
Debbie F.
The price is AU$906
includes taxes & fees
28 Sept - 29 Sept
The Links Lodge - Modern Golf and Beach Retreat
Exterior

19. OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA

OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
Old Orchard Beach
9.4 out of 10, Exceptional, (9 reviews)
"The property was perfect for our 3 day stay. It was very clean and had everything we needed. It was an easy walk to the beach and downtown. Would definitely use this property again. "
United States
Matthew V.
The price is AU$817
includes taxes & fees
7 Sept - 8 Sept
OOB family Beach House w/private yard and deck! Pet friendly, parking, 4/BR 2/BA
Property grounds

20. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is AU$801
includes taxes & fees
7 Sept - 8 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

10/10 Excellent
"We always stay here when we are in Portland visiting family. A friendly welcoming and fun place. Great bar, the bartender remembered me from 6 months ago. Great breakfast. Don’t miss the chef made omelettes, wow delicious. The lobby is comfortable and a great place to hang out."
Leah 5-night trip
Posted 6 hours ago
Embassy Suites by Hilton Portland Maine

Find out more about Portland

Portland Holiday Homes information

Number of reviews
15,860
Accommodation
79 Holiday Homes
Lowest Price
AU$133
Highest Price
AU$351

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