Holiday Homes in Portland

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Check prices for these dates

Our top choices for Portland holiday homes

1. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is NZ$623
includes taxes & fees
11 Nov - 12 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

2. Charming West End Victorian

Charming West End Victorian
Parkside
The price is NZ$1,206
includes taxes & fees
1 Dec - 2 Dec
Charming West End Victorian

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 NZ$1,070
includes taxes & fees
11 Nov - 12 Nov
Spacious Portland Home + Parking

4. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Chic 3-bedroom house in Munjoy Hill with off-street parking.
Munjoy Hill
10.0 out of 10, Exceptional, (10 reviews)
"Wow, wow, wow! My family and I all agree that this has been the best rental home we have ever stayed in. The interior design is so chic, we were truly wowed by the attention to detail in this place. The beds and pillows are also extremely comfy, we all had a great two nights of sleep here. The location of this place is phenomenal, it neighbors the Portland Observatory, many bars/cafes, and is a short walk down to the eastern promenade. We will absolutely stay here again the next time we’re in...
United States
Maris P.
The price is NZ$700
includes taxes & fees
11 Nov - 12 Nov
Chic 3-bedroom house in Munjoy Hill with off-street parking.

5. The 87th Townhome by Everrow

The 87th Townhome by Everrow
West End
9.6 out of 10, Exceptional, (11 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 NZ$924
includes taxes & fees
11 Nov - 12 Nov
The 87th Townhome by Everrow

6. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$930
includes taxes & fees
11 Nov - 12 Nov
Modern & Sunny East End House.

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 NZ$1,108
includes taxes & fees
12 Nov - 13 Nov
Willard Square Family Home

8. 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, (23 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is NZ$1,507
includes taxes & fees
11 Nov - 12 Nov
Spacious 4-bedroom house located in the heart of Portland, ME.

9. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space
Downtown Portland
The price is NZ$2,186
includes taxes & fees
8 Dec - 9 Dec
Steps to Old Port, balcony, private outdoor space

10. 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, (17 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.
The price is NZ$1,350
includes taxes & fees
8 Dec - 9 Dec
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

11. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is NZ$1,844
includes taxes & fees
12 Nov - 13 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

12. 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 NZ$4,773
includes taxes & fees
16 Nov - 17 Nov
Charming Historic Estate | In-town location

13. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$607
includes taxes & fees
11 Nov - 12 Nov
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 NZ$1,162
includes taxes & fees
11 Nov - 12 Nov
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 NZ$818
includes taxes & fees
11 Nov - 12 Nov
Fully Updated Airy Historic Home in South Freeport

16. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is NZ$1,102
includes taxes & fees
16 Nov - 17 Nov
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

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 NZ$708
includes taxes & fees
16 Nov - 17 Nov
Orchid Harbor, Bailey Island 3BR

18. Upscale OOB Beach House ♦ Seasonal Heated Pool

Upscale OOB Beach House ♦ Seasonal Heated Pool
Old Orchard Beach
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful remodel with plenty of beds and rooms. Came for son’s graduation from UNE. If we come back to OOB, would stay again in a heartbeat. "
United States
Kristen S.
The price is NZ$870
includes taxes & fees
12 Nov - 13 Nov
Upscale OOB Beach House ♦ Seasonal Heated Pool

19. Seaside Retreat by Everrow

Seaside Retreat by Everrow
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 NZ$745
includes taxes & fees
11 Nov - 12 Nov
Seaside Retreat by Everrow

20. Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi

Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
Old Orchard Beach
10.0 out of 10, Exceptional, (1 review)
"The property was very nice and what my family needed. It was exactly what I expected of a beach bungalow in the OOB area. The beds were surprising and so comfortable and while the shower was small, the water pressure was so nice. We would absolutely come back! The owner was very communicative and quick to respond."
United States
Amy S.
The price is NZ$527
includes taxes & fees
22 Nov - 23 Nov
Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
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.

Portland and related destinations

Stroll along the waterfront, savouring fresh lobster rolls before hopping a Casco Bay Lines ferry to explore nearby islands. Immerse yourself in culture at Portland Museum of Art, then catch live music at the historic State Theatre or Merrill Auditorium.

A lighthouse and houses on a rocky coastline with the ocean in the background.

Top reviews in Portland

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