A rocky shoreline with a lighthouse and a calm sea under a colorful sky.

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Peaks Island holiday homes

A backyard with a white wooden fence, a small bush, a white wicker bench, and a stone wall in the background.

1. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
West End
8.4 out of 10, Very good, (65 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is £254
includes taxes & fees
16 Nov - 17 Nov
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A wooden picnic table with a bench, set on a grassy lawn.

2. 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.
Willard Square Family Home
A storefront with a sign reading 'LB KITCHEN' and a window display advertising 'MORNING THINGS COFFEE LUNCH BOWLS'.

3. Modern & Sunny East End House.

Modern & Sunny East End House.
Munjoy Hill
10.0 out of 10, Exceptional, (51 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is £385
includes taxes & fees
16 Nov - 17 Nov
Modern & Sunny East End House.
A kitchen with white cabinetry, a marble countertop, and a gas stove.

4. 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 £628
includes taxes & fees
16 Nov - 17 Nov
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.

5. 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, (85 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is £767
includes taxes & fees
16 Nov - 17 Nov
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A wooden covered porch with a green door, potted plants, and a red watering can.

6. Charming West End Victorian

Charming West End Victorian
Parkside
The price is £522
includes taxes & fees
2 Dec - 3 Dec
Charming West End Victorian
A modern kitchen with a large island, bar stools, and a view through large windows.

7. 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, (17 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 £580
includes taxes & fees
22 Nov - 23 Nov
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A staircase with wooden railings, two wooden chairs with cushions, a small table with a lamp, and a potted plant.

8. 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 £347
includes taxes & fees
16 Nov - 17 Nov
Fully Updated Airy Historic Home in South Freeport
A red building with a front door, a bay window, and a brick pathway.

9. 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 £443
includes taxes & fees
16 Nov - 17 Nov
Spacious Portland Home + Parking
A two-story brick building with a front porch, a black door, and a window with a white frame.

10. The 87th Townhome by Everrow

The 87th Townhome by Everrow
West End
9.6 out of 10, Exceptional, (11 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 £380
includes taxes & fees
16 Nov - 17 Nov
The 87th Townhome by Everrow
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

11. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is £262
includes taxes & fees
16 Nov - 17 Nov
Quiet Spot in lovely Freeport neighborhood
A courtyard with outdoor seating, a staircase leading to a building, and blooming trees.

12. Steps to Old Port, balcony, private outdoor space

Steps to Old Port, balcony, private outdoor space
Downtown Portland
The price is £1,151
includes taxes & fees
15 Dec - 16 Dec
Steps to Old Port, balcony, private outdoor space
An outdoor patio area with a pergola, seating, and a garden.

13. 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 £2,048
includes taxes & fees
16 Nov - 17 Nov
Charming Historic Estate | In-town location
A rocky shoreline at sunset with calm water and distant land.

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 £301
includes taxes & fees
13 Dec - 14 Dec
Orchid Harbor, Bailey Island 3BR
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

15. Heated Game Room, Coastal Maine Cape Sleeps 10

Heated Game Room, Coastal Maine Cape Sleeps 10
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is £691
includes taxes & fees
16 Nov - 17 Nov
Heated Game Room, Coastal Maine Cape Sleeps 10
Two Adirondack chairs by a lake with trees and a clear sky.

16. 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 £1,160
includes taxes & fees
30 Nov - 1 Dec
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A house surrounded by trees and a body of water.

17. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
Windham
9.8 out of 10, Exceptional, (43 reviews)
"Beautiful location and property! "
United States
Michael S.
The price is £519
includes taxes & fees
1 Dec - 2 Dec
Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!
A wooden deck with outdoor seating and string lights.

18. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Great house! Enjoyed our stay very much. Comfortable, clean, and many nice extra touches i.e. games, books."
United States
Jill J.
The price is £254
includes taxes & fees
30 Nov - 1 Dec
Full sized home
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

19. 5BR Family Dream with Private Beach Access

5BR Family Dream with Private Beach Access
Old Orchard Beach
9.0 out of 10, Wonderful, (10 reviews)
"Proximity to beach and the beach were excellent. If stairs are an issue to you, this is not the house for you. Beds are comfortable and outdoor showers very nice . House is a bit dated."
United States
Ann L.
The price is £381
includes taxes & fees
22 Nov - 23 Nov
5BR Family Dream with Private Beach Access
A house with a stone pathway leading to the front door, surrounded by lush greenery and a lake view.

20. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"This little spot was an ideal getaway for our family’s summer trip to Maine. We very much enjoyed the porch with a view of the water and felt right at home here."
United States
James C.
The price is £257
includes taxes & fees
18 Nov - 19 Nov
Mere Point Sunrise Views at Eastern Shore!
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 Peaks Island Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"The staff was very friendly and the hotel was very quaint. It was also in the perfect location."
Staci 3-night trip
Posted less than an hour ago
Portland Harbor Hotel

Find out more about Peaks Island

Peaks Island Holiday Homes information

Number of reviews
368
Accommodation
666 Holiday Homes
Lowest Price
£254
Highest Price
£2,048