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

Portland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Portland vacation 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 CA $135
CA $515 total
includes taxes & fees
Oct 29 - Oct 30
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A red building with a front door, a bay window, and a brick pathway.

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 CA $231
CA $899 total
includes taxes & fees
Oct 26 - Oct 27
Spacious Portland Home + Parking
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.

3. 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 CA $267
CA $585 total
includes taxes & fees
Nov 11 - Nov 12
Chic 3-bedroom house in Munjoy Hill with off-street parking.
A two-story brick building with a front porch, a black door, and a window with a white frame.

4. The 87th Townhome by Everrow

The 87th Townhome by Everrow
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 CA $261
CA $758 total
includes taxes & fees
Oct 26 - Oct 27
The 87th Townhome by Everrow
A kitchen with white cabinets, a radiator, and a dining area with a floral chair and a chessboard.

5. Charming West End Victorian

Charming West End Victorian
Parkside
The price is CA $287
CA $1,012 total
includes taxes & fees
Oct 26 - Oct 27
Charming West End Victorian
A room with a large sliding glass door leading to a balcony with chairs and potted plants.

6. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (49 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is CA $420
CA $713 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $501
CA $949 total
includes taxes & fees
Nov 12 - Nov 13
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.

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 CA $707
CA $1,273 total
includes taxes & fees
Oct 28 - Oct 29
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.

9. 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, (84 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is CA $977
CA $1,556 total
includes taxes & fees
Oct 26 - Oct 27
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

10. 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 CA $2,268
CA $3,698 total
includes taxes & fees
Nov 1 - Nov 2
Charming Historic Estate | In-town location
A window with a view of a snowy landscape and bare trees.

11. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
9.4 out of 10, Exceptional, (3 reviews)
"Great location. Very nice place."
United States
Bernie G.
The price is CA $161
CA $461 total
includes taxes & fees
Oct 30 - Oct 31
Tranquility between the Lakes & Sea
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

12. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is CA $118
CA $466 total
includes taxes & fees
Oct 26 - Oct 27
Quiet Spot in lovely Freeport neighborhood
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

13. 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 CA $200
CA $682 total
includes taxes & fees
Oct 26 - Oct 27
Fully Updated Airy Historic Home in South Freeport
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

14. 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 CA $196
CA $548 total
includes taxes & fees
Oct 27 - Oct 28
Orchid Harbor, Bailey Island 3BR
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 CA $466
CA $984 total
includes taxes & fees
Nov 4 - Nov 5
Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland
Kitchen and center island

16. 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 CA $251
CA $809 total
includes taxes & fees
Oct 27 - Oct 28
Upscale Spacious OOB Beach House - Seasonal Heated Pool
A narrow hallway with white walls, a blue carpet, and a door leading outside.

17. 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 CA $184
CA $666 total
includes taxes & fees
Oct 26 - Oct 27
Seaside Retreat by Everrow
A covered porch with a view of a lake and trees.

18. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is CA $205
CA $552 total
includes taxes & fees
Nov 17 - Nov 18
Mere Point Sunrise Views at Eastern Shore!
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 CA $132
CA $280 total
includes taxes & fees
Oct 26 - Oct 27
Mid Coast Getaway w/ water views
A lush garden with a hammock, a variety of flowers, and a lake in the background.

20. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is CA $490
CA $2,354 total
includes taxes & fees
Nov 23 - Nov 24
Classic New England Waterfront House Big Lawn Beautiful Sunrise
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

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

8/10 Good
"Staff and room were perfectly fine. Breakfast meh, but as expected."
Keenann 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Find out more about Portland

Portland Vacation Homes information

Number of reviews
283
Accommodation
82 Vacation Homes
Lowest Price
CA $280
Highest Price
CA $3,698

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