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

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 $137
CA $525 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $312
CA $1,007 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $307
CA $822 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $394
CA $1,153 total
includes taxes & fees
Oct 29 - Oct 30
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, (47 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is CA $426
CA $722 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.

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 CA $508
CA $961 total
includes taxes & fees
Nov 14 - Nov 15
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.
The price is CA $717
CA $1,290 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $566
CA $1,015 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $589
CA $1,138 total
includes taxes & fees
Oct 18 - Oct 19
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 CA $990
CA $1,577 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $2,299
CA $3,748 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $164
CA $466 total
includes taxes & fees
Oct 18 - Oct 19
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 CA $152
CA $516 total
includes taxes & fees
Oct 18 - Oct 19
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 CA $351
CA $862 total
includes taxes & fees
Oct 25 - Oct 26
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.
The price is CA $250
CA $618 total
includes taxes & fees
Oct 27 - Oct 28
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)
The price is CA $559
CA $1,468 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $324
CA $913 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $149
CA $309 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $369
CA $1,231 total
includes taxes & fees
Oct 28 - Oct 29
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

8/10 Good
"The location was perfect to walk around and explore the port. Easily discover restaurants,shops, and directly across from art museum. Room had a nice bay view (extra for bay) surfaces were clean but need a more thorough cleaning as we found items under the couch. Food options are available but with so many restaurants only steps away I would venture out from the hotel. Breakfast was standard buffet,did not have their dinner (available at buffet location). Pool and amenities seemed underutilized and neglected as pool was freezing (stated that pool was 86 but felt like 64), a bit dirt need to be removed and saunas took a long time to heat up. Not terrible just kinda of there. Gym looked ok. Staff was a bit of a mix bag, First Lady was helpful but blunt( we were early so I get it), second who check us in had computer issues not her fault but she forgot to give us food vouchers lucky later we asked and received , third gave us food vouchers and was very very kind and helpful. If you visit make sure you’re not early, tell them you have the breakfast, and if the pool is cold tell someone. Easy access to parking garage but pricey (should be included with stay… hey who said that) recommend for travelers with no car as old port is near and area is walkable."
Marissa 2-night trip
Posted 6 hours ago
Holiday Inn Portland-By the Bay by IHG

Find out more about Portland

Portland Vacation Homes information

Number of reviews
219
Accommodation
82 Vacation Homes
Lowest Price
CA $309
Highest Price
CA $3,757

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