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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (63 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is €326
includes taxes & fees
20 Oct - 21 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.
Spacious Portland Home + Parking
A two-story brick building with a front porch, a black door, and a window with a white frame.

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 €529
includes taxes & fees
2 Nov - 3 Nov
The 87th Townhome - Local Landmark
A kitchen with white cabinets, a radiator, and a dining area with a floral chair and a chessboard.

4. Charming West End Victorian

Charming West End Victorian
Parkside
The price is €734
includes taxes & fees
18 Oct - 19 Oct
Charming West End Victorian
A storefront with the sign "OYSTERS" and a "RAW BAR" sign above the entrance.

5. 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 €448
includes taxes & fees
18 Oct - 19 Oct
Modern & Sunny House Steps from the Promenade.
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 €593
includes taxes & fees
12 Nov - 13 Nov
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, (22 reviews)
"Great space for our needs: three generations for a graduation weekend!"
United States
Matt H.
Spacious 4-bedroom house located in the heart of Portland, ME.
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

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 €631
includes taxes & fees
31 Oct - 1 Nov
Gorgeous 3-bedroom house in charming Portland
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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.
The price is €721
includes taxes & fees
18 Oct - 19 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.

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, (82 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is €991
includes taxes & fees
18 Oct - 19 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.

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
A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

12. Whole Home | Sleeps 16 | Roof Deck|5 mins Downtown

Whole Home | Sleeps 16 | Roof Deck|5 mins 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.
Whole Home | Sleeps 16 | Roof Deck|5 mins Downtown
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 €313
includes taxes & fees
15 Nov - 16 Nov
Tranquility between the Lakes & Sea
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

14. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is €315
includes taxes & fees
18 Oct - 19 Oct
Quiet Spot in lovely Freeport neighborhood
A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

15. 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 €541
includes taxes & fees
25 Oct - 26 Oct
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

16. 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.
Orchid Harbor, Bailey Island 3BR
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

17. 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 €918
includes taxes & fees
25 Oct - 26 Oct
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Kitchen and center island

18. 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, (20 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 €586
includes taxes & fees
20 Oct - 21 Oct
Upscale Spacious OOB Beach House - Seasonal Heated Pool
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

19. 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 €196
includes taxes & fees
17 Nov - 18 Nov
Mid Coast Getaway w/ water views
A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

20. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.6 out of 10, Exceptional, (4 reviews)
"It was perfect for our girls trip to Portland. Private, surrounded by woods, cozy and clean! We even saw wild turkeys and deer in the yard."
United States
Jonny D.
The price is €774
includes taxes & fees
28 Oct - 29 Oct
Windham Lakefront: Fire Pit and Modern Comforts
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 rooms were spacious and clean. We couldn’t have found a better breakfast by eating out! Each morning the staff had an immaculate breakfast bar! The location was great for walking to the shops and eating out at night."
Shannon 4-night trip
Posted less than an hour ago
Hampton Inn Portland Downtown - Waterfront

Find out more about Portland

Portland Holiday Homes information

Number of reviews
220
Accommodation
80 Holiday Homes
Lowest Price
€196
Highest Price
€991