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
25 Sep - 27 Sep
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 vacation homes

Interior

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 AED 463
AED 1,473 total
includes taxes & fees
12 Oct - 13 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
TV, fireplace

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.
The price is AED 873
AED 1,976 total
includes taxes & fees
14 Sep - 15 Sep
Rare West End Home • Walk to Old Port, Harbor View
Exterior

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.
The price is AED 1,469
AED 2,680 total
includes taxes & fees
14 Sep - 15 Sep
Willard Square Family Home
Outdoor dining

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 AED 1,311
AED 2,366 total
includes taxes & fees
15 Sep - 16 Sep
The Globe House on Munjoy Hill - Walk to Breweries
Outdoor dining

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 AED 808
AED 2,606 total
includes taxes & fees
13 Sep - 14 Sep
Spacious Portland Home + Parking
Outdoor dining

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 AED 1,264
AED 2,050 total
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.
Interior

7. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 474
AED 1,261 total
includes taxes & fees
6 Oct - 7 Oct
Tranquility between the Lakes & Sea
Exterior detail

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 AED 2,902
AED 4,369 total
includes taxes & fees
15 Sep - 16 Sep
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Exterior

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 AED 1,174
AED 2,605 total
includes taxes & fees
16 Sep - 17 Sep
The 87th Townhome - Local Landmark
Interior

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 AED 1,521
AED 2,986 total
includes taxes & fees
28 Sep - 29 Sep
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
Interior

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 AED 2,314
AED 5,353 total
includes taxes & fees
15 Sep - 16 Sep
Entire Home | Sleeps 16 | w/ Roof Deck | 5 mins to Downtown
Coffee/tea maker, fridge, microwave, dishwasher

12. Quiet Spot in lovely Freeport desert pines neighborhood

Quiet Spot in lovely Freeport desert pines neighborhood
Freeport
The price is AED 520
AED 1,494 total
includes taxes & fees
14 Sep - 15 Sep
Quiet Spot in lovely Freeport desert pines neighborhood
Terrace/patio

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 AED 744
AED 1,355 total
includes taxes & fees
22 Sep - 23 Sep
Full sized home
Property grounds

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.
Orchid Harbor, Bailey Island 3BR
Dining

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 AED 1,506
AED 3,659 total
includes taxes & fees
22 Sep - 23 Sep
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Smart TV

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.
Luxe 5 Bed/ 3 Bath with Game Room & AC
TV, offices

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.
Windham Lakefront: Fire Pit and Modern Comforts
TV, fireplace, offices

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.
Charming Historic Estate | In-town location
TV

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 AED 482
AED 917 total
includes taxes & fees
20 Sep - 21 Sep
Mid Coast Getaway w/ water views
Property grounds

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 AED 1,484
AED 2,130 total
includes taxes & fees
12 Sep - 13 Sep
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"The staff was absolutely amazing and so helpful. Such a nice quaint place and very clean. We loved the free breakfast in the mornings!"
Bailey 3-night trip
Posted less than an hour ago
Inn at St John Portland In-Town

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