A marina with various boats docked at wooden piers, a bridge in the background, and a forested hillside.

Kittery Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Kittery holiday rentals

An outdoor seating area with tables and chairs, a metal railing, and a view of buildings in the background.

1. Treadwell Mansion

Treadwell Mansion
4.0 star property
Downtown
9.4 out of 10, Exceptional, (19 reviews)
"Rooms and location are absolutely perfect!"
United States
Kathy
The price is NZ$461
includes taxes & fees
2 Nov - 3 Nov
Treadwell Mansion
A wooden door with a brass anchor handle, a staircase with a patterned wall, and a window with a number "3" on the right.

2. Great Island Inn

Great Island Inn
3.5 star property
New Castle
10.0 out of 10, Exceptional, (127 reviews)
"Fantastic location, beautiful views it’s a gem on the island!"
United States
Craig
The price is NZ$389
includes taxes & fees
1 Nov - 2 Nov
Great Island Inn
Garden

3. Rye Motor Inn - Oceanfront, Walk to Beach

Rye Motor Inn - Oceanfront, Walk to Beach
3.0 star property
Rye
9.6 out of 10, Exceptional, (130 reviews)
"Amazing stay and place"
United States
Amanda
The price is NZ$243
includes taxes & fees
19 Oct - 20 Oct
Rye Motor Inn - Oceanfront, Walk to Beach
A coastal town with a marina filled with boats, surrounded by residential buildings and a clear sky.

4. Amazing harbor/ocean views of Pepperrell Cove

Amazing harbor/ocean views of Pepperrell Cove
Kittery
10.0 out of 10, Exceptional, (33 reviews)
"They thought of everything in this house. We loved it. All the rooms have a beautiful view, and the location was very convenient."
United States
Rachel F.
The price is NZ$1,085
includes taxes & fees
12 Nov - 13 Nov
Amazing harbor/ocean views of Pepperrell Cove
A room with a wooden floor, a sofa, a table, and a window with curtains.

5. Great Island Inn - King Studio Apt - Main Street View

Great Island Inn - King Studio Apt - Main Street View
New Castle
10.0 out of 10, Exceptional, (4 reviews)
"Our rental was perfect. It had everything we needed and more. We will definitely return next year. No complaints."
United States
pamela s.
The price is NZ$626
includes taxes & fees
3 Nov - 4 Nov
Great Island Inn - King Studio Apt - Main Street View
The Perch`s living room

6. The Perch on Penhallow, Downtown Portsmouth

The Perch on Penhallow, Downtown Portsmouth
Downtown
9.8 out of 10, Exceptional, (14 reviews)
"Our hosts were extremely accommodating. We had a wonderful stay. Great place in a great location."
United States
Susan G.
The Perch on Penhallow, Downtown Portsmouth
A spacious living area with a high ceiling, exposed wooden beams, a large sofa, a coffee table, and a kitchen in the background.

7. The Penthouse at Penhallow

The Penthouse at Penhallow
Downtown
10.0 out of 10, Exceptional, (17 reviews)
"Great location. Kitchen was well stocked. Beds were comfortable and bathrooms nice. Will rent again."
United States
Kimberlee
The price is NZ$974
includes taxes & fees
20 Oct - 21 Oct
The Penthouse at Penhallow
A room with a fireplace, a ceiling fan, a mirror, and a door leading to another room.

8. Historical Apt. In Downtown Portsmouth

Historical Apt. In Downtown Portsmouth
West End
10.0 out of 10, Exceptional, (5 reviews)
"I had such an amazing stay!! The apartment was perfect and had everything you could possibly need. Having the market across the street was so convenient. You can walk to everything in town. I wish I could have stayed longer!"
United States
Amanda D.
The price is NZ$410
includes taxes & fees
9 Nov - 10 Nov
Historical Apt. In Downtown Portsmouth
A hotel room with a large window overlooking a harbor, a marble table, and a bottle of champagne.

9. Tugboat Vista 2 Bedroom Downtown Portsmouth

Tugboat Vista 2 Bedroom Downtown Portsmouth
Downtown
10.0 out of 10, Exceptional, (18 reviews)
"Great space, great location."
United States
Patrick R.
The price is NZ$614
includes taxes & fees
2 Nov - 3 Nov
Tugboat Vista 2 Bedroom Downtown Portsmouth
A modern kitchen with wooden flooring, white cabinetry, a central island with stools, and a view of the outdoors through large windows.

10. Bright Bungalow, King-size Bed, Fence-in Backyard–Cool, Cozy & Dog Friendly

Bright Bungalow, King-size Bed, Fence-in Backyard–Cool, Cozy & Dog Friendly
South Eliot
10.0 out of 10, Exceptional, (4 reviews)
"Very cute, perfect for us and our pup."
United States
Christine B.
The price is NZ$664
includes taxes & fees
21 Oct - 22 Oct
Bright Bungalow, King-size Bed, Fence-in Backyard–Cool, Cozy & Dog Friendly
A modern living room with a sofa, a dining table, and a kitchen area.

11. Music City Vibe ~ Luxe ~ PVT Deck ~ DWTN ~ <2min to MKT SQ

Music City Vibe ~ Luxe ~ PVT Deck ~ DWTN ~ <2min to MKT SQ
Downtown
10.0 out of 10, Exceptional, (22 reviews)
"Fabulous location. Can walk any where downtown.Apartment is lovely, has everything you need and the host is helpful andresponsive."
United States
Susan M.
Music City Vibe ~ Luxe ~ PVT Deck ~ DWTN ~ <2min to MKT SQ
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with bar stools.

12. Sleep up to 12, quick access to Kittery and Portsmouth, Beaches, Boat Launch

Sleep up to 12, quick access to Kittery and Portsmouth, Beaches, Boat Launch
South Eliot
10.0 out of 10, Exceptional, (5 reviews)
"The owner was extremely helpful, fast communication and went out of his way to offer hospitality."
United States
Ashley B.
The price is NZ$1,166
includes taxes & fees
1 Nov - 2 Nov
Sleep up to 12, quick access to Kittery and Portsmouth, Beaches, Boat Launch
A cozy living area with a round table, wicker chairs, a sofa, and a TV stand.

13. Chic Loft-Style Condo in Downtown Portsmouth

Chic Loft-Style Condo in Downtown Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay. Reminder that there is no oven/stove so plan accordingly."
United Kingdom
Anonymous traveller
The price is NZ$765
includes taxes & fees
3 Nov - 4 Nov
Chic Loft-Style Condo in Downtown Portsmouth
A wooden deck with outdoor seating, string lights, and a brick wall.

14. Market Street Loft in Historic Downtown Portsmouth

Market Street Loft in Historic Downtown Portsmouth
Downtown
9.8 out of 10, Exceptional, (27 reviews)
"Great place to stay! Just be prepared for a lot of stairs."
United States
grace o.
The price is NZ$474
includes taxes & fees
26 Oct - 27 Oct
Market Street Loft in Historic Downtown Portsmouth
A bedroom with a large bed, two bedside lamps, a ceiling light, a skylight, a wooden dresser, and a mirror on the wall.

15. Downtown Portsmouth 2 Bedroom 2 King Beds

Downtown Portsmouth 2 Bedroom 2 King Beds
Downtown
9.4 out of 10, Exceptional, (13 reviews)
"Nice little VRBO for a quick stay. Beds were comfortable, clean uncluttered layout, close to everything."
United States
Tim B.
The price is NZ$522
includes taxes & fees
3 Nov - 4 Nov
Downtown Portsmouth 2 Bedroom 2 King Beds
A deck with outdoor furniture, including sofas and a table, and large windows on the house.

16. Serenity @ Snug Harbor | Ocean View | Private Deck

Serenity @ Snug Harbor | Ocean View | Private Deck
Rye
9.8 out of 10, Exceptional, (23 reviews)
"Seamless process, great view of the ocean, clean property. Overall great experience."
United States
Kyle B.
Serenity @ Snug Harbor | Ocean View | Private Deck
A swimming pool with lounge chairs and a covered area, surrounded by trees and a building in the background.

17. Pink Blossom Family Resort

Pink Blossom Family Resort
3.0 star property
Ogunquit
9.6 out of 10, Exceptional, (329 reviews)
"It was great and a great location."
United States
Robert
The price is NZ$271
includes taxes & fees
20 Oct - 21 Oct
Pink Blossom Family Resort
A snow-covered dome structure with a bench and a basket, overlooking a body of water during sunset.

18. Lovely Waterfront Suite near Portsmouth

Lovely Waterfront Suite near Portsmouth
Dover
10.0 out of 10, Exceptional, (154 reviews)
"Beautiful location on the river while also centrally located. Lovely space filled with fresh flowers and treats."
United States
Lin G.
The price is NZ$531
includes taxes & fees
1 Nov - 2 Nov
Lovely Waterfront Suite near Portsmouth
A deck with wicker furniture and a table, surrounded by a white railing.

19. Harbor Serenity | Private Deck | Mins to Beach

Harbor Serenity | Private Deck | Mins to Beach
Rye
9.0 out of 10, Wonderful, (14 reviews)
"Great spot, close to Wallis Sands State Beach. Ocean view visible from both sides of force porch area. Would stay again."
United States
William G.
The price is NZ$752
includes taxes & fees
20 Oct - 21 Oct
Harbor Serenity | Private Deck | Mins to Beach
A picnic area with tables and an umbrella, a wooden building, and a white picket fence.

20. Sands Resort at Hampton Beach

Sands Resort at Hampton Beach
2.0 star property
Hampton Beach
8.4 out of 10, Very good, (59 reviews)
"Great stay"
United States
Phillip
The price is NZ$367
includes taxes & fees
16 Oct - 17 Oct
Sands Resort at Hampton 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 Kittery Hotel Reviews

Hampton Inn & Suites Portsmouth Downtown

Hampton Inn & Suites Portsmouth Downtown

10/10 Excellent
"Awesome stay !"
Dondre 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Portsmouth Downtown

Find out more about Kittery

Everything you need to know about Kittery holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kittery holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kittery holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kittery holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kittery. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kittery holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kittery holiday rentals we have selected for you start as low as NZ$243 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kittery rentals

At Expedia, we put the best Kittery holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kittery rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kittery holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kittery. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

STUNNING BEACHSIDE HOME-WELLS BEACH: 180 DEGREE OCEAN VIEWS: 9-1 to 9-3 open: This holiday home rental outside of Kittery is located on the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Kittery?

Choose from 20 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. Kittery Premium Outlets and Hampton Beach are a couple of places you'll find in the wider area.

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.