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

Peaks Island Holiday Rentals

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Our top choices for Peaks Island holiday rentals

1. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (113 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is NZ$821
includes taxes & fees
18 Oct - 19 Oct
Ocean View East End Studio in a Historic Victorian

2. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (185 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is NZ$825
includes taxes & fees
18 Oct - 19 Oct
Glorious getaway on Portland's Eastern Promenade.

3. 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, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is NZ$2,037
includes taxes & fees
5 Oct - 6 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

4. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is NZ$505
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade

5. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
The price is NZ$447
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland

6. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is NZ$838
includes taxes & fees
26 Oct - 27 Oct
Arlie`s Digs! - One Block To Willard Beach!

7. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (8 reviews)
"Excellent in every way."
United States
Robert B.
The price is NZ$608
includes taxes & fees
27 Oct - 28 Oct
Willard Beach–Apartment Near Portland & Parks

8. Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful apartment. Great location. Very comfortable and all amenities needed."
United States
Navina F.
The price is NZ$1,116
includes taxes & fees
28 Oct - 29 Oct
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

9. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$382
includes taxes & fees
6 Oct - 7 Oct
Beautiful 1st Floor Apartment & Amazing Shower

10. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$1,002
includes taxes & fees
5 Oct - 6 Oct
Modern & Sunny House Steps from the Promenade.

11. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is NZ$710
includes taxes & fees
5 Oct - 6 Oct
Peaceful & minutes from the Old Port with private parking

12. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"5 star in every way"
United States
Doug F.
Harborview - Curated East End Escape w/ Parking

13. 2 Bedroom Apartment on Top Floor in Portland's West End

2 Bedroom Apartment on Top Floor in Portland's West End
West End
10.0 out of 10, Exceptional, (88 reviews)
"The rooftop deck makes the climb worth it. Everything was clean neat and organized. Great beds. Communication was fast and friendly. Thanks for a great stay. "
United States
TODD H.
The price is NZ$857
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom Apartment on Top Floor in Portland's West End

14. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (122 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$798
includes taxes & fees
25 Oct - 26 Oct
The Weldon Hotel

15. Bright & Sunny West End Apartment with Private Parking.

Bright & Sunny West End Apartment with Private Parking.
West End
10.0 out of 10, Exceptional, (58 reviews)
"LOCATION, SUPER CLEAN & BRIGHT - LOVED OUR STAY!"
United States
JODY H.
The price is NZ$932
includes taxes & fees
1 Oct - 2 Oct
Bright & Sunny West End Apartment with Private Parking.

16. Island View House BnB Self Check-in # 3 / Free Parking

Island View House BnB Self Check-in # 3 / Free Parking
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"Good amount of space for our family group, beautiful old house, updated and clean, super friendly hosts, great location for beach/pier area access."
United States
Denise D.
The price is NZ$1,484
includes taxes & fees
5 Oct - 6 Oct
Island View House BnB Self Check-in # 3 / Free Parking

17. Newly Renovated 2nd Floor Apt near USM

Newly Renovated 2nd Floor Apt near USM
Oakdale
10.0 out of 10, Exceptional, (17 reviews)
"Property is very nice, in a nice location, easy to walk to various stores/locations. It was well stocked with all the basics we would need."
United States
mary m.
The price is NZ$1,155
includes taxes & fees
5 Oct - 6 Oct
Newly Renovated 2nd Floor Apt near USM

18. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (62 reviews)
"Very clean and has a lot of amenities"
United States
Philip
Spacious 3 BR in Portland's Libbytown!

19. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (34 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is NZ$567
includes taxes & fees
5 Oct - 6 Oct
Sunny Spot with Private Parking.

20. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (13 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,212
includes taxes & fees
27 Oct - 28 Oct
Evalina Hotel
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

Find out more about Peaks Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Peaks Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Peaks Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Peaks Island. Seeing all the best attractions is bound to make you fall in love with Peaks Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Peaks Island short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a holiday rental in Peaks Island?

Yes, there are holiday rentals close to the most popular sights in Peaks Island, or you can select a more secluded option if you're looking for a relaxing stay. Peaks Island is known for its architecture and mountain views. Make sure you have time to check out the restaurants and festivals during your trip.

What are some of the best holiday rentals that Peaks Island has to offer?

NEW LISTING ☼ Unique Oceanfront Home. Separate boat rental available.: This highly rated holiday home rental in Peaks Island is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a garden. Another good choice for your trip to Peaks Island is Absolutely Breathtaking Direct Oceanfront Cottage ~ Perfect Location!.

How many holiday rentals will I find in Peaks Island?

With 24 Expedia holiday rentals, you're guaranteed to find just the right place for your Peaks Island stay.

What can I see and do in Peaks Island?

Cultural attractions to visit include Fifth Maine Museum and Richard Boyd Art Gallery. Umbrella Cover Museum and Battery Steele are other places to visit while you're in town.

What are holiday rentals like in Peaks Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Peaks Island. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.