A waterfront marina with boats docked, a wooden house with a balcony, and autumn-colored trees in the background.

Kennebunkport Holiday Rentals

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Our top choices for Kennebunkport holiday rentals

1. Elmwood Resort Hotel

Elmwood Resort Hotel
3.0 star property
Wells
9.4 out of 10, Exceptional, (454 reviews)
"Loved the pool, great atmosphere and check-in was so smooth and easy"
United States
Dawna
The price is NZ$314
includes taxes & fees
27 Sept - 28 Sept
Elmwood Resort Hotel

2. Village by the Sea

Village by the Sea
3.5 star property
Wells
9.0 out of 10, Wonderful, (561 reviews)
"Friendly staff,clean rooms will definitely book again"
United States
Dylan
The price is NZ$338
includes taxes & fees
18 Oct - 19 Oct
Village by the Sea

3. Pink Blossom Family Resort

Pink Blossom Family Resort
3.0 star property
Ogunquit
9.6 out of 10, Exceptional, (322 reviews)
"Spacious and very clean. Super convenient to everything!"
United States
Donna
The price is NZ$266
includes taxes & fees
12 Oct - 13 Oct
Pink Blossom Family Resort

4. Moody Beach RV Campground

Moody Beach RV Campground
2.0 star property
Wells
8.6 out of 10, Excellent, (37 reviews)
"Great place to stay! Owners are very accommodating!"
United States
Kathleen A.
The price is NZ$318
includes taxes & fees
19 Oct - 20 Oct
Moody Beach RV Campground

5. 1/2 Mi to Pier: Wfh-friendly Apt in Maine!

1/2 Mi to Pier: Wfh-friendly Apt in Maine!
3.0 star property
Old Orchard Beach
The price is NZ$589
includes taxes & fees
30 Sept - 1 Oct
1/2 Mi to Pier: Wfh-friendly Apt in Maine!

6. Huttopia Southern Maine

Huttopia Southern Maine
2.5 star property
Sanford
9.0 out of 10, Wonderful, (47 reviews)
"I love the property and our tent was very comfortable. It was our first time camping and we truly enjoyed the property and its amenities. I will definitely make this annual tradition."
United States
Valerie
The price is NZ$240
includes taxes & fees
27 Sept - 28 Sept
Huttopia Southern Maine

7. Oceanfront Home - Beach Access - Deck + Ping Pong

Oceanfront Home - Beach Access - Deck + Ping Pong
3.5 star property
Old Orchard Beach
The price is NZ$4,757
includes taxes & fees
27 Sept - 28 Sept
Oceanfront Home - Beach Access - Deck + Ping Pong

8. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,347
includes taxes & fees
21 Sept - 22 Sept
Evalina Hotel

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (118 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$863
includes taxes & fees
19 Oct - 20 Oct
The Weldon Hotel

10. 'beachfront 9' Condo on Old Orchard Beach

'beachfront 9' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NZ$495
includes taxes & fees
30 Sept - 1 Oct
'beachfront 9' Condo on Old Orchard Beach

11. 'beachfront 14' Condo on Old Orchard Beach

'beachfront 14' Condo on Old Orchard Beach
3.0 star property
Old Orchard Beach
The price is NZ$646
includes taxes & fees
20 Sept - 21 Sept
'beachfront 14' Condo on Old Orchard Beach

12. Walk to Pier & Ocean: Apt in Old Orchard Beach!

Walk to Pier & Ocean: Apt in Old Orchard Beach!
4.0 star property
Old Orchard Beach
6.0 out of 10, (1 review)
"This is an old house, and certain features could be deemed charming. The beds were comfortable, and we appreciated some of the amenities. However, it seemed worn and bare-bones in some aspects. For example, the AC in one of the bedrooms was a stand-alone unit that was jerry-rigged to vent out the window, and the other bedroom had no AC. The screen door was broken. There were hardly any utensils and no bowls. The hairdryer “high” setting was broken and could only be used on “low”. For only a...
United States
Lawrence
The price is NZ$567
includes taxes & fees
20 Sept - 21 Sept
Walk to Pier & Ocean: Apt in Old Orchard Beach!
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 Kennebunkport Hotel Reviews

Find out more about Kennebunkport

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 Kennebunkport 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 Kennebunkport. 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 Kennebunkport. Seeing all the best attractions is bound to make you fall in love with Kennebunkport. 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 Kennebunkport short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Kennebunkport?

Yes, there are holiday rentals close to the most popular sights in Kennebunkport, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Kennebunkport speak positively about the popular beaches and top-notch restaurants in this destination. Leave some time to check out the shops and waterfront during your trip.

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

Quintessential Maine Beach Cottage: This highly rated holiday home rental in Kennebunkport is located on the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Kennebunkport?

With 178 Expedia holiday rentals, you're guaranteed to find just the right place for your Kennebunkport stay.

What’s there to see and do in Kennebunkport?

Enjoy the outdoors at Kennebunkport Village Green and Goose Rocks Beach, or simply take in cultural attractions like Seashore Trolley Museum and First Families Kennebunkport Museum. Other places in town to visit include Dock Square and Walker's Point.

What’s a holiday rental in Kennebunkport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kennebunkport. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for a family trip.