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.

AED 1,285 total

includes taxes & fees

9 Nov - 10 Nov

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.

AED 1,461 total

includes taxes & fees

11 Nov - 12 Nov

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

12 Nov - 13 Nov

A storefront with the sign 'OYSTERS' and a 'RAW BAR' sign above the entrance. There are outdoor seating areas with tables and chairs.

4. Modern & Sunny East End House.

Munjoy Hill

stacey p.

AED 1,945 total

includes taxes & fees

9 Nov - 10 Nov

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.

AED 3,175 total

includes taxes & fees

9 Nov - 10 Nov

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 3,899 total

includes taxes & fees

12 Nov - 13 Nov

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

7. Charming West End Victorian

Parkside

AED 2,664 total

includes taxes & fees

1 Dec - 2 Dec

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

8. Spacious Portland Home + Parking

Parkside

Ellen M.

AED 2,238 total

includes taxes & fees

9 Nov - 10 Nov

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

9. 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 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 1,927 total

includes taxes & fees

9 Nov - 10 Nov

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

Downtown Portland

AED 4,664 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

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.

13. Charming Historic Estate | In-town location

West End

shelley w.

AED 10,357 total

includes taxes & fees

9 Nov - 10 Nov

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

Harpswell

Jane D.

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

15. Newly Renovated Luxury House with Game Room

Yarmouth

Michelle T.

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

16. Quiet Spot in lovely Freeport neighborhood

Freeport

AED 1,259 total

includes taxes & fees

9 Nov - 10 Nov

A lush garden with a hammock, a variety of flowers, and a lake in the background.

17. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Harpswell

Ashma B.

AED 5,869 total

includes taxes & fees

30 Nov - 1 Dec

A wooden deck with outdoor seating and string lights.

18. Full sized home

Harpswell

Erika T.

AED 1,277 total

includes taxes & fees

30 Nov - 1 Dec

A covered porch with a view of a lake and trees.

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

Windham

Michael S.

AED 2,393 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a large wooden dining table, white chairs, and a hanging light fixture.

20. Family Tides by Bayley Vacation Rentals

Pine Point

"This was our second time staying at this beautiful, comfortable, and very spacious beach house. It is extremely well equipped and stocked in every way, from beach chairs to games and puzzles. The kitchen amenities and supplies are plentiful (we especially love the twin dishwashers) and made it easy to prepare meals for our for our multi-generational family of 14. The location is great, very easy beach access, and we rode the local trolley down to Old Orchard Beach for extra fun. There are also a...

andrea g.

AED 11,128 total

includes taxes & fees

20 Nov - 21 Nov

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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 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 modern bar area with a wooden bar counter, black bar stools, and a contemporary light fixture.

AC Hotel Portland Downtown/Waterfront, ME

Downtown Portland

10/10 Excellent

Craig

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

Embassy Suites by Hilton Portland Maine

Portland

10/10 Excellent

Michael

A balcony with a table and chairs, overlooking a street with buildings and parked cars.

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 view from a window overlooking a body of water with a distant shoreline, a vase with flowers, and a glass on a table.

The McKernan Inn

South Portland

10/10 Excellent

elizabeth

A balcony with wooden flooring, striped cushioned chairs, and a glass railing overlooking a cityscape at night.

Hyatt Place Portland Downtown - Old Port Square

Downtown Portland

10/10 Excellent

Douglas

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

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 modern bar area with a bar counter, seating, and a view of the cityscape.

Aloft by Marriott Portland Downtown Waterfront ME

Downtown Portland

10/10 Excellent

Lindsay

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

A spacious living room with a large dining table, comfortable seating, and large windows offering views of the city.

The Docent's Collection at 121 Middle Street

Downtown Portland

10/10 Excellent

Jeffrey

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