A pier extending into a body of water with a backdrop of residential buildings and trees.

Search Vacation Homes in Peaks Island

Dates

November 2026

December 2026

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Our top choices for Peaks Island 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 ♦ Walk to Old Port

West End

Susan d.

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.

2. 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.

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

3. Willard Square Family Home

Willard Beach

David W.

AED 2,360 total

includes taxes & fees

21 Nov - 22 Nov

A modern kitchen with a central island, a dining area with a sofa and chairs, and a living room with a colorful rug and plants.

4. Modern & Sunny East End House.

Munjoy Hill

stacey p.

AED 2,163 total

includes taxes & fees

5 Dec - 6 Dec

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

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

Munjoy Hill

Matt H.

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

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

East Deering

Mike G.

AED 4,240 total

includes taxes & fees

2 Dec - 3 Dec

A red building with a front door, a bay window, and a brick pathway.

7. Spacious Portland Home + Parking

Parkside

Ellen M.

AED 2,138 total

includes taxes & fees

8 Nov - 9 Nov

A wooden covered porch with a green door, potted plants, and a red watering can.

8. Charming West End Victorian

Parkside

AED 2,690 total

includes taxes & fees

1 Dec - 2 Dec

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

North Deering

Patrick J.

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

West End

Amy B.

AED 2,723 total

includes taxes & fees

5 Dec - 6 Dec

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

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

Scarborough

Stuart R.

AED 2,316 total

includes taxes & fees

9 Nov - 10 Nov

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

12. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

AED 1,694 total

includes taxes & fees

11 Nov - 12 Nov

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

Downtown Portland

A two-story house with a stone staircase leading to a front door, surrounded by a garden with potted plants and a seating area with chairs.

14. Charming Historic Estate | In-town location

West End

shelley w.

A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

15. Orchid Harbor, Bailey Island 3BR

Harpswell

Jane D.

AED 1,296 total

includes taxes & fees

10 Nov - 11 Nov

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

16. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

AED 2,486 total

includes taxes & fees

9 Nov - 10 Nov

A dining area with a wooden table and chairs, a red sofa, and a small round table with a decorative plate.

17. Quiet Spot in lovely Freeport neighborhood

Freeport

AED 1,259 total

includes taxes & fees

21 Nov - 22 Nov

A bedroom with two beds, a wooden dresser, a nightstand with a lamp, and a bookshelf.

18. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

AED 6,009 total

includes taxes & fees

6 Dec - 7 Dec

A wooden deck with outdoor seating and string lights.

19. Full sized home

Harpswell

Erika T.

AED 1,273 total

includes taxes & fees

8 Dec - 9 Dec

A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

20. 5BR Family Dream with Private Beach Access

Old Orchard Beach

Bradford P.

View all properties

Learn more about Peaks Island

Rent bikes to explore this charming island's rocky beaches, historic forts, and the Fifth Maine Regiment Museum. Take the 20-minute ferry from Portland for kayaking adventures, seafood dining at Island Lobster Company, or swimming at Sandy Beach.

See all hotels in Peaks Island

Top reviews in Peaks Island

Inn On Peaks Island

Peaks Island

10/10 Excellent

Devon

An outdoor patio area with wicker furniture, string lights, and a barbecue grill.

Residence Inn by Marriott Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Mark

A modern living room with a sofa, two armchairs, a glass coffee table, and a decorative wall panel.

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Craig

A rooftop terrace with a modern outdoor seating area, a fire pit, and a view of the cityscape.

Cambria Hotel Portland Downtown-Old Port

Downtown Portland

10/10 Excellent

seth

A spacious lobby with multiple seating areas, a fireplace, and large windows.

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Michael

A waterfront marina with boats docked, buildings with multiple windows, and a red building with a visible restaurant.

Hilton Garden Inn Portland Downtown Waterfront

Downtown Portland

10/10 Excellent

Robert

A brick building with a red awning labeled "Chateau Riverside."

Portland Regency Hotel & Spa

Downtown Portland

10/10 Excellent

This property is beautiful. It sits in the historic area of the old port. It is very close to the waterfront, restaurants, shops and historic areas. The mattress and sheets were superb. While in the old port, we took a trolley tour which took us out to Portland headlight and then gave us a tour of of the old port. You can catch fairies from about two or three minutes walk away, we would strongly recommend this hotel.

Debra

A modern living room with a large sectional sofa, a dining area with a kitchen in the background, and large windows offering a city view.

The Press Hotel, Marriott Autograph Collection

Downtown Portland

10/10 Excellent

RII

A brick building with a large bay window, a covered porch, and a staircase leading to the entrance.

The McKernan Inn

South Portland

10/10 Excellent

elizabeth

A swimming pool with lounge chairs and tables, indoor lighting, and a ceiling with ventilation.

Holiday Inn Portland-By the Bay by IHG

Downtown Portland

10/10 Excellent

Sherry

A historic building with classical architecture, featuring a prominent tower and ornate columns.

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Excellent

Douglas

An outdoor seating area with a fire feature, comfortable seating, and a view of a waterfront.

Canopy by Hilton Portland Waterfront

Downtown Portland

10/10 Excellent

Noah

The exterior of a Courtyard by Marriott hotel with a glass entrance, outdoor seating area, and a stone facade.

Courtyard Portland Downtown/Waterfront

Downtown Portland

10/10 Excellent

Anonymous traveler

A fire pit surrounded by wicker chairs in a garden setting.

Portland Harbor Hotel

Downtown Portland

10/10 Excellent

Christopher

A multi-story building with a stone facade, large windows, and a corner entrance.

Evalina Hotel

Downtown Portland

10/10 Excellent

Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation...

Christopher