A cityscape with a prominent church steeple, various buildings, and lush green trees.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Portland holiday homes

A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

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 £294
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

2. 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 £532
includes taxes & fees
30 Sept - 1 Oct
Spacious Portland Home + Parking
A living room with a sofa, a coffee table, and a vase on a windowsill.

3. Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View
West End
9.8 out of 10, Exceptional, (16 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
The price is £419
includes taxes & fees
1 Oct - 2 Oct
Rare West End Home • Walk to Old Port, Harbor View
A two-story brick building with a front porch, a black door, and a window with a white frame.

4. 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 £480
includes taxes & fees
27 Oct - 28 Oct
The 87th Townhome - Local Landmark
A two-story house with a balcony, a covered patio, and a fenced yard.

5. 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, (109 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is £504
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

6. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is £423
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.
A building named Willard Square with a storefront and a red vehicle parked outside.

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 £454
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A living room with a sofa, coffee table, and a large rug. There is a dining area with chairs and a table. The room has a mural on the wall depicting a landscape.

8. 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, (9 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 £523
includes taxes & fees
23 Oct - 24 Oct
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

9. 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, (20 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is £695
includes taxes & fees
28 Oct - 29 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.2 out of 10, Wonderful, (14 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is £637
includes taxes & fees
30 Sept - 1 Oct
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

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, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is £923
includes taxes & fees
6 Oct - 7 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A living room with a fireplace, leather sofa, and a chandelier.

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 £2,067
includes taxes & fees
20 Oct - 21 Oct
Charming Historic Estate | In-town location
A window with a view of a snowy landscape and bare trees.

13. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is £247
includes taxes & fees
4 Oct - 5 Oct
Tranquility between the Lakes & Sea
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

14. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 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 £158
includes taxes & fees
30 Sept - 1 Oct
Mid Coast Getaway w/ water views
A beach with footprints, a person standing, and birds on the sand.

15. Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton

Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
Buxton
8.0 out of 10, Very good, (2 reviews)
"Place was clean and cozy. Big yard for games and a fire pit for s’mores. Based on previous review I brought pots/pans but didn’t need them. Everything was available. Stove is gas and I was not familiar with using one so that was the only “challenge”We had a ball and the place was perfect for us!!"
United States
Anonymous traveller
The price is £263
includes taxes & fees
1 Oct - 2 Oct
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A narrow hallway with white walls, a blue carpet, and a door leading outside.

16. Adorable Seaside Cottage

Adorable Seaside Cottage
Old Orchard Beach
8.0 out of 10, Very good, (5 reviews)
"Overall nice small place, owner responded quickly to issues. "
United States
Qi L.
The price is £354
includes taxes & fees
30 Sept - 1 Oct
Adorable Seaside Cottage
A wooden deck with Adirondack chairs overlooking a beach.

17. The Brunswick #450 by Bayley Vacation Rentals

The Brunswick #450 by Bayley Vacation Rentals
Old Orchard Beach
7.6 out of 10, Good, (4 reviews)
"Ideal view and location in terms of proximity to Palace Playland, restaurants and shops. We did not accurately anticipate the noise level of the almost nightly bands that played at the downstairs restaurant/bar. So if you’re a couple without kids or a single person who does not mind that then the location can’t be beat. I definitely would not recommend if you’re looking for peace and relaxation in the evening hours. Again, that’s our own fault for not taking that into consideration before...
United States
Gretchen R.
The price is £666
includes taxes & fees
30 Sept - 1 Oct
The Brunswick #450 by Bayley Vacation Rentals
A spacious living room with large windows, a sofa, a chair, and a small table.

18. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
1 Mi to Maine Street! MCM-Style Home in Brunswick
A bedroom with a bed, a window with curtains, a wall-mounted lamp, and a view of the outside.

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

Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
Old Orchard Beach
Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

20. 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 £521
includes taxes & fees
1 Oct - 2 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"It was convenient"
Matthew 2-night trip
Posted 5 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Portland

Portland Holiday Homes information

Number of reviews
379
Accommodation
82 Holiday Homes
Lowest Price
£158
Highest Price
£2,067