Holiday houses in Kennebunkport

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars7 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.89 out of 5 average rating, 205 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

BrandonRating, 5 stars2 weeks ago

What a wonderful stay my family and I had! With two small children it was so nice to be in walking distance of so much! My wife especially took advantage of the coffee shop next door! Would recommend to family and friends and plan on booking again next year!

4.98 out of 5 average rating, 330 reviews

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

WarrenRating, 5 stars1 month ago

Hillary's place was a wonderful place to stay for a cozy weekend getaway. It felt very homey with personal touches. We were here during a little snowstorm so we didn't spend any time outside but the yard and private deck were really nice. We had some troubles with the hot water but Hillary was very responsive and helpful! We would definitely stay here again.

4.94 out of 5 average rating, 128 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

RachaelRating, 5 stars2 days ago

Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

5 out of 5 average rating, 3 reviews

Home in Wells

"In Tempore" Cottage

AllisonRating, 5 stars9 months ago

Gisele and her property manager were promptly responsive. The cottage was extremely clean, newly decorated and well appointed. The layout was very comfortable for our family of four. The pools were nice and not overly crowded. The only negatives were: If not taking the trolley or golf cart, the closest pool was a half mile walk with no parking available. The further pool did have parking. Also, no outside water source/hose to rinse off. Plenty of restaurant choices nearby in Wells, Ogunquit and Kennebunkport. Wells beaches were beautiful with easy, affordable parking. Overall a wonderful stay in Wells!

Townhouse in Kennebunkport

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

TreenaRating, 5 stars4 months ago

I can’t say enough about this experience. The house was a great location for my mother’s 70th and Jennifer went the extra mile (literally) to make this a memorable experience for the celebration weekend. She is so easy to communicate with. Exceptional host, all the way around!

Apartment in Kennebunkport

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

EmilyRating, 5 stars8 months ago

My husband and I stayed at Kristen’s apartment for 2 weeks at the end of August and had the most amazing time! This was our 3rd time to KPT and most definitely our favorite thanks to this gorgeous Airbnb and Kristen’s hospitality. The apartment was perfect for us — was exactly as described, better than the photos with amazing windows and views, speedy WiFi perfect for working remotely. It’s a quick 4 minute drive into town, and such a beautiful area to walk around. Kristen was so responsive and helpful — there’s a super extensive list of local reccs in the apartment, and a beach pass that you can use during your stay. We loved this home away from home, and can’t wait to come back soon!

4.83 out of 5 average rating, 140 reviews

Apartment in East End

Fall in LOVE With PORTLAND, MAINE

OliviaRating, 5 stars1 month ago

Stayed for a weekend with 5 people - the space was perfect us! With 3 beds and 2 baths we didn’t feel on top of each other inside. We opted for free street parking which was never an issue. There’s a handful of coffee shops, restaurants and bars with 5-10 min walk. Old Port is about 20 min walk but very easy and safe. We loved being around the block from the ocean and east prom!!

5 out of 5 average rating, 26 reviews

Home in Ogunquit

Hoyts Ahoy

JulieRating, 5 stars1 month ago

We had a wonderful weekend celebrating St. Patty’s Day up in Ogunquit. The property was everything we had hoped for in a rental. Everything was comfortable and clean. The house is spacious and a great place to get your day started. You can’t beat the location! Off the beaten path, but a few minutes of walking to downtown. The host was super responsive to my questions. I would absolutely stay here again.

Holiday rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Kennebunkport holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Kennebunkport's top sights

Gooch's Beach51 locals recommend

Old Vines Wine Bar66 locals recommend

Pedro's Mexican Restaurant54 locals recommend

Federal Jack's51 locals recommend

Earth at Hidden Pond44 locals recommend

Mothers Beach39 locals recommend

Other great holiday rentals in Kennebunkport

4.93 out of 5 average rating, 59 reviews

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

ShellyRating, 5 stars1 week ago

Gregory's place was great for our 2 night getaway. Hot tub was amazing and private from neighbors. Bathrooms and kitchens were well stocked. I will definitely go back for another getaway

4.9 out of 5 average rating, 79 reviews

Home in Hampton

Lux Getaway! Perfect for Groups 8+ppl

AhmedRating, 5 stars5 months ago

Josh and Tracy are very nice and friendly and their place is amazing! I highly recommend their place to anyone visiting the area!

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

4.94 out of 5 average rating, 16 reviews

Home in Sandown

Sunrise Beach Escape

DebraRating, 5 stars1 week ago

This was the perfect location for our family to spend spring break together! The teenagers loved the games and hot tub, and the adults loved sitting on the patio and chit chatting. The beds were all comfortable, and the window air-conditioning units let each room pick their comfortable temperature. There is plenty of space in the kitchen, and the house had a ton of items available! They provided sufficient paper towels, toilet paper, and dishwasher soap (which so many do not) We all enjoyed the pinball enough that we definitely had to get an extra few rolls of quarters for our 5 night trip. We also all don't do well with the Melaluca brand products that the house uses, so we got our own soaps. There are so many great spaces on the property, and we would have spent even more time outdoors if the weather was warmer, but there was SO much to do inside! We all kept commenting how perfect it was for our group of 6 adults, 2 teens, and 2 tweens.

5 out of 5 average rating, 9 reviews

Apartment in Hampton

Beachside Bliss: Hampton North Beach Condo

LindaRating, 5 stars19 months ago

Great place that’s got everything you need. Just like advertised. Nice and safe area, very close proximity to the beach. Joe is a great host, very responsive and will make sure you feel right at home.

4.9 out of 5 average rating, 94 reviews

Home in Freedom

Our Mountain Retreat – Lake Ossipee Access

FinRating, 5 stars1 month ago

Paula’s was the perfect spot for a weekend trip with a group of friends for my birthday! It had plenty of sleeping spots for us and was very comfortable, and we really loved the hot tub. They were such responsive and communicative hosts as well, and offered us a flexible late check-out. Thank you!

Apartment in Old Orchard Beach

5 out of 5 average rating, 50 reviews

Horizon View Hideaway with Deck

ReneeRating, 5 stars6 months ago

The house is beautiful and very comfortable. We had everything we needed. The host was very friendly and responsive. We would definitely stay there again.