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Holiday Homes in Portland

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Our top choices for Portland holiday homes

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, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

2. 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$951
includes taxes & fees
2 Nov - 3 Nov
The 87th Townhome - Local Landmark

3. 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$994
includes taxes & fees
1 Nov - 2 Nov
Spacious Portland Home + Parking

4. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (48 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$714
includes taxes & fees
1 Nov - 2 Nov
Modern & Sunny House Steps from the Promenade.

5. Charming West End Victorian

Charming West End Victorian
Parkside
Charming West End Victorian

6. 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, (22 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is AU$1,286
includes taxes & fees
20 Oct - 21 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.

7. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (13 reviews)
"Thoroughly enjoyed this house! "
United States
David W.
The price is AU$952
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home

8. Gorgeous 3-bedroom house in charming Portland

Gorgeous 3-bedroom house in charming Portland
North Deering
9.0 out of 10, Wonderful, (4 reviews)
"This place was exactly as it looks in the photos. Really conveniently located with good amenities."
United States
Bridget M.
The price is AU$965
includes taxes & fees
31 Oct - 1 Nov
Gorgeous 3-bedroom house in charming Portland

9. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (16 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

10. 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, (83 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is AU$1,685
includes taxes & fees
26 Oct - 27 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

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.
The price is AU$3,673
includes taxes & fees
2 Nov - 3 Nov
Charming Historic Estate | In-town location

12. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Very nice property. Plenty of room and as advertised. Comfy beds. Owner very responsive."
United States
Thomas C.
The price is AU$461
includes taxes & fees
22 Oct - 23 Oct
Tranquility between the Lakes & Sea

13. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is AU$466
includes taxes & fees
20 Oct - 21 Oct
Quiet Spot in lovely Freeport neighborhood

14. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Scarborough
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. Alexa was a great host. Having garaged parking and the indoor pool/hot tub was perfect for our stay that coincided with a snow. Would definitely stay here again next winter."
United States
Stuart R.
The price is AU$856
includes taxes & fees
25 Oct - 26 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

15. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
10.0 out of 10, Exceptional, (1 review)
"Great property well kept and close to everything we wanted to do"
United States
boodu
The price is AU$682
includes taxes & fees
20 Oct - 21 Oct
Fully Updated Airy Historic Home in South Freeport

16. Adorable Seaside Cottage

Adorable Seaside Cottage
Old Orchard Beach
8.4 out of 10, Very good, (6 reviews)
"Overall nice small place, owner responded quickly to issues. "
United States
Qi L.
The price is AU$632
includes taxes & fees
20 Oct - 21 Oct
Adorable Seaside Cottage

17. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is AU$600
includes taxes & fees
27 Oct - 28 Oct
Orchid Harbor, Bailey Island 3BR

18. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
The price is AU$1,478
includes taxes & fees
25 Oct - 26 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port

19. Upscale Spacious OOB Beach House - Seasonal Heated Pool

Upscale Spacious OOB Beach House - Seasonal Heated Pool
Old Orchard Beach
10.0 out of 10, Exceptional, (22 reviews)
"There is plenty of space to sleep within the home. Having the pool in the back yard was awesome, we tended to use the pool more than going to the beach because it was fogged in."
United States
Karen R.
The price is AU$916
includes taxes & fees
25 Oct - 26 Oct
Upscale Spacious OOB Beach House - Seasonal Heated Pool

20. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is AU$314
includes taxes & fees
1 Nov - 2 Nov
Mid Coast Getaway w/ water 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

Portland Holiday Homes information

Number of reviews
217
Accommodation
79 Holiday Homes
Lowest Price
AU$314
Highest Price
AU$3,673

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