Peaks Island Holiday Homes from £168: Search Holiday Homes in Peaks Island

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

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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

West End

Susan d.

includes taxes & fees

29 Oct - 30 Oct

A building named Willard Square with a storefront and a red vehicle parked outside.

2. Willard Square Family Home

Willard Beach

David W.

includes taxes & fees

14 Oct - 15 Oct

An outdoor seating area with tables and benches in front of a building with a sign reading "BRAKES & SHOCKS Specialty Bakery".

3. Spacious Portland Home + Parking

Parkside

Ellen M.

A living room with a sofa, a coffee table, and a vase on a windowsill.

4. Rare West End Home • Walk to Old Port, Harbor View

West End

Nikki W.

A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

5. Modern & Sunny House Steps from the Promenade.

Munjoy Hill

stacey p.

includes taxes & fees

13 Oct - 14 Oct

A two-story house with a balcony, a covered patio, and a fenced yard.

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

Munjoy Hill

Richard D.

includes taxes & fees

6 Oct - 7 Oct

A window with a view of a snowy landscape and bare trees.

7. Tranquility between the Lakes & Sea

Westbrook

includes taxes & fees

5 Oct - 6 Oct

A two-story brick building with a front porch, a black door, and a window with a white frame.

8. The 87th Townhome - Local Landmark

West End

Amy B.

includes taxes & fees

26 Oct - 27 Oct

A kitchen with a wooden island, black bar stools, a hanging light fixture, and a framed botanical print on the wall.

9. Spacious 4-bedroom house located in the heart of Portland, ME.

Munjoy Hill

Matt H.

includes taxes & fees

28 Oct - 29 Oct

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.

10. Chic 3-bedroom house in Munjoy Hill with off-street parking.

Munjoy Hill

"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...

Maris P.

includes taxes & fees

29 Oct - 30 Oct

A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

11. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

East Deering

Sally O.

includes taxes & fees

6 Oct - 7 Oct

A sunroom with a glass ceiling, outdoor seating, a hot tub, and a stone wall.

12. Coastal Retreat - Sauna, Hot Tub & Swim Spa - Near Beaches and Downtown Portland

Scarborough

Stuart R.

includes taxes & fees

1 Oct - 2 Oct

A living room with a sofa, armchair, wooden coffee table, and a potted plant.

13. Fully Updated Airy Historic Home in South Freeport

Freeport

includes taxes & fees

1 Oct - 2 Oct

A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

14. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

North Deering

Peter H.

includes taxes & fees

5 Oct - 6 Oct

A wooden deck with outdoor seating and string lights.

15. Full sized home

Harpswell

Angela M.

includes taxes & fees

7 Oct - 8 Oct

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

16. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

12 Oct - 13 Oct

A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

17. Mid Coast Getaway w/ water views

West Point

Rebecca

includes taxes & fees

4 Oct - 5 Oct

A dirt path in a park with autumn foliage.

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

Westbrook

Genevieve W.

includes taxes & fees

6 Oct - 7 Oct

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.

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

Westbrook

damean s.

includes taxes & fees

6 Oct - 7 Oct

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

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

Yarmouth

Michelle T.

includes taxes & fees

1 Oct - 2 Oct

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Top Peaks Island Hotel Reviews

Portland Regency Hotel & Spa

8/10 Good

"Choose this hotel for the excellent location and proximity to things downtown not for a high end experience. This hotel has a great walkable location, was comfortable, and relatively clean. It needs some updating but we were only there to sleep so didn’t mind."

Spark by Hilton Portland Airport Maine Mall

10/10 Excellent

"Room and property was very clean and organized. I had a chance to use the treadmill in the gym, worked great since I was traveling and needed some exercise. 24hr coffee in the lobby is my favorite especially since we left for the airport at 3:30am. Close and convenient for the Jetport airport in Portland Maine."