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

Holiday Homes in Portland

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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 NZ$675
includes taxes & fees
19 Oct - 20 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 NZ$1,228
includes taxes & fees
27 Sept - 28 Sept
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.
Rare West End Home • Walk to Old Port, Harbor View
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

4. 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 NZ$902
includes taxes & fees
27 Sept - 28 Sept
Modern & Sunny House Steps from the Promenade.
A two-story brick building with a front porch, a black door, and a window with a white frame.

5. 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 NZ$1,084
includes taxes & fees
28 Sept - 29 Sept
The 87th Townhome - Local Landmark
A building named Willard Square with a storefront and a red vehicle parked outside.

6. 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$1,062
includes taxes & fees
14 Oct - 15 Oct
Willard Square Family Home
A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

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, (20 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
The price is NZ$1,646
includes taxes & fees
20 Oct - 21 Oct
Spacious 4-bedroom house located in the heart of Portland, ME.
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

8. 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 NZ$1,963
includes taxes & fees
28 Sept - 29 Sept
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.

9. 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$4,725
includes taxes & fees
6 Oct - 7 Oct
Charming Historic Estate | In-town location
A window with a view of a snowy landscape and bare trees.

10. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$569
includes taxes & fees
29 Sept - 30 Sept
Tranquility between the Lakes & Sea
A living room with a grey sofa, two patterned armchairs, a round wicker coffee table, and a flat-screen TV mounted on the wall.

11. 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 NZ$917
includes taxes & fees
27 Oct - 28 Oct
Huge New Townhome 10mins from the Beach
A picnic table by a lake with trees and a white fence in the background.

12. Couple's Glamping Getaway on Bonny Eagle Pond

Couple's Glamping Getaway on Bonny Eagle Pond
Buxton
10.0 out of 10, Exceptional, (14 reviews)
"Great location! Exceptionally clean and comfortable."
United States
ALYSSA
Couple's Glamping Getaway on Bonny Eagle Pond
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

13. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is NZ$713
includes taxes & fees
24 Oct - 25 Oct
Quiet Spot in lovely Freeport neighborhood
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 NZ$353
includes taxes & fees
30 Sept - 1 Oct
Mid Coast Getaway w/ water views
A narrow hallway with white walls, a blue carpet, and a door leading outside.

15. 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 NZ$831
includes taxes & fees
30 Sept - 1 Oct
Adorable Seaside Cottage
A beach with footprints, a person standing, and birds on the sand.

16. 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 NZ$587
includes taxes & fees
27 Sept - 28 Sept
Center of Everything Southern Maine… 3-bedroom house, huge yard in Buxton
A bedroom with a bed, a window with curtains, a wall-mounted lamp, and a view of the outside.

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

Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
Old Orchard Beach
The price is NZ$673
includes taxes & fees
27 Sept - 28 Sept
Coastal Retreat! 5 MIN Walk to the Beach + Jacuzzi
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

18. 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$1,207
includes taxes & fees
1 Oct - 2 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

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, (19 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.
Upscale Spacious OOB Beach House - Seasonal Heated Pool
A wooden deck with outdoor seating and string lights.

20. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (70 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is NZ$640
includes taxes & fees
5 Oct - 6 Oct
Full sized home
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"The room was spacious. We asked for a view and received a room with a water view."
Debra 2-night trip
Posted 3 hours ago
Hampton Inn Portland Downtown - Waterfront

Find out more about Portland

Portland Holiday Homes information

Number of reviews
354
Accommodation
79 Holiday Homes
Lowest Price
NZ$353
Highest Price
NZ$4,725

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