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

Holiday Homes in Peaks Island

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Peaks Island 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 €331
includes taxes & fees
20 Sept - 21 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a sofa, a coffee table, and a vase on a windowsill.

2. 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, (14 reviews)
"Lovely stay & Jordan was very helpful & accommodating"
United States
Nikki W.
Rare West End Home • Walk to Old Port, Harbor View
A building named Willard Square with a storefront and a red vehicle parked outside.

3. Willard Square Family Home

Willard Square Family Home
Willard Beach
9.8 out of 10, Exceptional, (12 reviews)
"Great location, close to Old Port. Great bakery/coffee and ice cream next door. House was clean and comfortable!"
United States
Steve S.
Willard Square Family Home
A two-story house with a balcony, a covered patio, and a fenced yard.

4. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is €548
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

5. 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 €618
includes taxes & fees
14 Sept - 15 Sept
Spacious Portland Home + Parking
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

6. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (43 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is €442
includes taxes & fees
14 Sept - 15 Sept
Modern & Sunny House Steps from the Promenade.
A window with a view of a snowy landscape and bare trees.

7. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is €304
includes taxes & fees
13 Oct - 14 Oct
Tranquility between the Lakes & Sea
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, (80 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is €1,016
includes taxes & fees
15 Sept - 16 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A two-story brick building with a front porch, a black door, and a window with a white frame.

9. 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 €593
includes taxes & fees
16 Sept - 17 Sept
The 87th Townhome - Local Landmark
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

10. 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, (13 reviews)
"Very nice! Would stay again and would highly recommend."
United States
Peter H.
The price is €680
includes taxes & fees
28 Sept - 29 Sept
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A modern interior with a glass door leading to an outdoor deck with a sofa and a hanging light fixture.

11. Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown

Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to 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.
The price is €1,226
includes taxes & fees
15 Sept - 16 Sept
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
A compact kitchen with a microwave, coffee maker, and a sink. There are cabinets, a dishwasher, and a dining table with chairs.

12. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is €357
includes taxes & fees
14 Sept - 15 Sept
Quiet Spot in lovely Freeport desert pines neighborhood
A wooden deck with outdoor seating and string lights.

13. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (68 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is €313
includes taxes & fees
22 Sept - 23 Sept
Full sized home
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, (12 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 €431
includes taxes & fees
2 Oct - 3 Oct
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.

15. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is €852
includes taxes & fees
22 Sept - 23 Sept
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

16. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful home! Everything about our stay was perfect. The home has everything you could possibly need and more. My family stayed for a long weekend and everyone was so happy with the accommodations. Hoping to go back!"
United States
Lisa L.
The price is €824
includes taxes & fees
14 Sept - 15 Sept
Luxe 5 Bed/ 3 Bath with Game Room & AC
A modern living room with a brown leather sofa, a rustic coffee table, and a dining area with a white table and chairs.

17. Windham Lakefront: Fire Pit and Modern Comforts

Windham Lakefront: Fire Pit and Modern Comforts
Windham
9.4 out of 10, Exceptional, (3 reviews)
"This is an exceptional property. It was quiet and comfortable, and we all slept well. The location was ideal for our plans and the host answered every question promptly.I highly recommend this rental, and I plan to return."
United States
Richard G.
The price is €629
includes taxes & fees
30 Sept - 1 Oct
Windham Lakefront: Fire Pit and Modern Comforts
A living room with a fireplace, leather sofa, and a chandelier.

18. 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 €2,371
includes taxes & fees
8 Oct - 9 Oct
Charming Historic Estate | In-town location
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
9.4 out of 10, Exceptional, (9 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 €216
includes taxes & fees
20 Sept - 21 Sept
Mid Coast Getaway w/ water views
A dirt path in a park with autumn foliage.

20. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is €495
includes taxes & fees
14 Sept - 15 Sept
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
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

Best Western Merry Manor Inn

Best Western Merry Manor Inn

10/10 Excellent
"Just such friendly helpful staff…. Really nice breakfast… nice clean property"
Marcee 1-night trip
Posted 2 hours ago
Best Western Merry Manor Inn

Find out more about Peaks Island

Peaks Island Holiday Homes information

Number of reviews
459
Accommodation
672 Holiday Homes
Lowest Price
€216
Highest Price
€2,371

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