Kittery Holiday Rentals

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Holiday Rentals in Kittery

Dog-friendly home with water view, firepit, large deck & yard - close to town

7.2 out of 10, Good, (11)
"Loved the deck!"
Dog-friendly home with water view, firepit, large deck & yard - close to town

Village by the Sea

3.5 star property
9.0 out of 10, Wonderful, (516)
"For the most part my 3 night stay was great. A few hiccups. Heating system use was difficult to figure out in the bedrooms. There were extra pillows but no extra blankets. TVs were hard to figure out if you’ve never used Roku. Otherwise place was great. Super clean and spacious. "
Village by the Sea

Amazing Beach House! 5 Bedroom across the Ocean!

10.0 out of 10, Exceptional, (102)
"Place is beautiful, spacious, and you could hear the ocean. Enjoyed the number if bedrooms, sitting rooms space"
Amazing Beach House! 5 Bedroom across the Ocean!

STUNNING NEW BEACHSIDE LISTING DIRECTLY ON WELLS BEACH: 9/28-10/3 OPEN NOW!

9.8 out of 10, Exceptional, (52)
"Wonderful property on ideal beach location. Excellent communication with the host . "
STUNNING NEW BEACHSIDE LISTING DIRECTLY ON WELLS BEACH: 9/28-10/3 OPEN NOW!

Condo w/ balcony, seasonal pool and pool table and walkable location

9.0 out of 10, Wonderful, (41)
"The "
Condo w/ balcony, seasonal pool and pool table and walkable location

Cozy Cottage!

9.6 out of 10, Exceptional, (18)
"The cottage is delightful, clean, cute and comfy! I will be back!"
Cozy Cottage!

Dog-friendly cottage with amazing sunset views, across the street from beach

8.8 out of 10, Excellent, (79)
"Its a nice little place. Very clean with an amazing view of the sunset from the couch or back yard. Kinda small though so id recommend just a couple people. Id stay again. The Beach is maybe a 5 minute walk away."
Dog-friendly cottage with amazing sunset views, across the street from beach

Tiny home steps from the beach.

9.6 out of 10, Exceptional, (30)
"Being steps from the beach was fabulous! And the tiny cottage was great … just as described! "
Tiny home steps from the beach.

Awesome location downtown. Walk to the beach, marginal way

10.0 out of 10, Exceptional, (148)
"Beautiful little cottage. Everything one could need! Very convenient and quiet location. Great communication with the owner, who was very thoughtful and helpful for our anniversary celebration trip. Thank you ! "
Awesome location downtown. Walk to the beach, marginal way

The Great Escape on Hampton Beach. Beach directly across the street.

10.0 out of 10, Exceptional, (60)
"From start to finish it was exceptional. Scott was a great host, checked in to see if we needed anything. The place was clean and had everything we could ever ask for. It was an amazing stay and we will definitely be back!"
The Great Escape on Hampton Beach. Beach directly across the street.

Rye Motor Inn: An Adults-Only Apartment Hotel

3.0 star property
9.8 out of 10, Exceptional, (57)
"Great apartment motel. I stayed 3 days. Quiet, super clean, and management could not have been more accommodating. "
The price is AU$277
includes taxes & fees
26 Nov - 27 Nov
Rye Motor Inn: An Adults-Only Apartment Hotel

Unique Beach and Ocean Panoramic Views, this home has it all !

10.0 out of 10, Exceptional, (160)
"We are regular visitors to this beautiful home. It is a favorite for its location, cleanliness and ease of communication with the owners. We look forward to our next return visit. "
Unique Beach and Ocean Panoramic Views, this home has it all !

Quaint Condo 5 Min.Walk To Perkins Cove

9.8 out of 10, Exceptional, (164)
"We really enjoyed staying in this beautifully decorated comfortable condo. Gloria was so friendly and accommodating before, and during our stay. The place is only about a mile away from the beautiful boat area where there are many quaint gift shops and restaurants. We had such a wonderful time exploring Ogunquit and the neighboring towns. We had the most fabulous time and would love to return sometime. Thank you Gloria for your amazing hospitality! "
Quaint Condo 5 Min.Walk To Perkins Cove

The Motel closest to the beach! Pet Friendly! The Best Surfing!

9.4 out of 10, Exceptional, (58)
"Clean motel type room across from the beach. Clean, great location, exactly what I needed."
The price is AU$238
includes taxes & fees
1 Dec - 2 Dec
The Motel closest to the beach! Pet Friendly! The Best Surfing!

Discount: Dec 17-22 available ! Epic ocean vista, a few steps to the beach

10.0 out of 10, Exceptional, (145)
"The house and location are gorgeous. The bedrooms are all nice but the two ocean facing rooms are fantastic. They are huge, all windows, and well appointed. Although there is no direct access to the beach, the walk down the hill is short and well worth it. The beach is lovely and has incredible sunrise views. I would have booked again for next year if there was availability!"
Discount: Dec 17-22 available ! Epic ocean vista, a few steps to the beach

Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

8.8 out of 10, Excellent, (20)
"The property is very close to the beach which is terrific. The second floor of the house was perfect for a great getaway. The technology worked perfectly. The bottom floor looked barren and dreary. The house was fairly clean and the appliances were modern."
Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD

10.0 out of 10, Exceptional, (102)
"It’s a fun little cottage and Julie is a wonderful host!"
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD

Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.

9.6 out of 10, Exceptional, (58)
"Sandra was a great host and IMMEDIATELY responded to ally our inquiries. The fenced in yard was great for the dog! Plenty of places to enjoy morning coffee outside. It was an easy walk to beach! We even found a bagel shop! "
Close to Beach! Pool, Hot Tub, Firepit in Patio area & Deck.

Charming, Dog-Friendly Cottage w/ Shared Pool - Walk to the Ocean

8.8 out of 10, Excellent, (41)
"Lovely little property exactly as described! There were a few minor cleanliness issues but the property team was receptive and helpful! Perfect location for going into Kennebunkport or to the beaches! Loved all the little shops and views! Enjoy your stay!"
Charming, Dog-Friendly Cottage w/ Shared Pool - Walk to the Ocean

Cozy Beach Front Home in York

10.0 out of 10, Exceptional, (106)
"The house was perfect for our needs. The absolutely wonderful location, right on the beach and walking distance to shops, is ideal. The house was very clean and well organized, and we didn't lack for anything. .We did have difficulty with the wifi one day, but the owners responded right away and the issue was taken care of immediately. I would definitely stay again! ps I found it a bit irritating that we needed to strip the beds and start the towel laundry, especially given that we pay for...
Cozy Beach Front Home in York
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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Other types of properties in Kittery you may be interested in

Coachman Inn

2.5 star property
7.8 out of 10, Good, (1004)
"The room was very comfortable and large. The beds were perfect. A little disappointed with the breakfast. It said full buffet breakfast. It was nothing like that. There wasn't even any fruit. Other than that our stay was great."
The price is AU$162
includes taxes & fees
9 Dec - 10 Dec
Coachman Inn

Kittery Inn and Suites

2.5 star property
9.2 out of 10, Wonderful, (1033)
"Great place, cozy very clean."
The price is AU$164
includes taxes & fees
1 Dec - 2 Dec
Kittery Inn and Suites

Hampton Inn & Suites Kittery-Portsmouth

2.5 star property
9.2 out of 10, Wonderful, (839)
"Place was clean and the bed was decent! We thoroughly enjoyed our stay! "
The price is AU$184
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Kittery-Portsmouth
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Kittery?

Yes, there are holiday rentals in Kittery close to Yummies Candy and Nuts, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Kittery is known for its array of shops and beaches. While you're here, grab a bite or have a drink at the restaurants.

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

Dog-friendly home with water view, firepit, large deck & yard - close to town: This highly rated holiday home rental in Kittery offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Kittery?

Choose from 19 Expedia holiday rentals in Kittery for a memorable holiday.

What can I see and do in Kittery?

Cultural attractions include Kittery Historical and Naval Museum, whereas Yummies Candy and Nuts is just one of the family-friendly sights. In the wider area, you’ll find popular places such as Hampton Beach and Ogunquit Beach.

What are holiday rentals like in Kittery?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kittery. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.