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

Holiday Rentals in Kittery

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Kittery holiday rentals

A modern bedroom with a bed, a desk, a chair, a sofa, and a wall-mounted TV.

1. Fresh + Modern Garden Level Kittery Studio

Fresh + Modern Garden Level Kittery Studio
Kittery
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was clean, bright and nicely decorated. We were greeted with some welcome snacks and locally made sodas. Erin was quick to send or answer messages with information. A pleasant place to stay."
United States
Debby K.
The price is €163
includes taxes & fees
28 Oct - 29 Oct
Fresh + Modern Garden Level Kittery Studio
A bedroom with a bed, a round wall shelf, a window, and a bedside table.

2. Rye Motor Inn - Oceanfront, Walk to Beach

Rye Motor Inn - Oceanfront, Walk to Beach
3.0 star property
Rye
9.8 out of 10, Exceptional, (132 reviews)
"Amazing stay and place"
United States
Amanda
The price is €94
includes taxes & fees
26 Oct - 27 Oct
Rye Motor Inn - Oceanfront, Walk to Beach
A wooden door with a brass anchor handle, a staircase with a patterned wall, and a window with a number "3" on the right.

3. Great Island Inn

Great Island Inn
3.5 star property
New Castle
10.0 out of 10, Exceptional, (129 reviews)
"Fantastic location, beautiful views it’s a gem on the island!"
United States
Craig
The price is €195
includes taxes & fees
1 Nov - 2 Nov
Great Island Inn
A room with a fireplace, a ceiling fan, a mirror, and a door leading to another room.

4. 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 €200
includes taxes & fees
26 Oct - 27 Oct
Historical Apt. In 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.

5. 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 €271
includes taxes & fees
26 Oct - 27 Oct
Downtown Portsmouth 2 Bedroom 2 King Beds
A wooden deck with outdoor seating, string lights, and a brick wall.

6. Market Street Loft in Historic Downtown Portsmouth

Market Street Loft in Historic Downtown Portsmouth
Downtown
9.8 out of 10, Exceptional, (28 reviews)
"Great place to stay! Just be prepared for a lot of stairs."
United States
grace o.
Market Street Loft in Historic Downtown Portsmouth
A modern living room with a brown leather sofa, two armchairs, a coffee table, and a flat-screen TV mounted on the wall.

7. Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ

Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ
Downtown
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful, extremely clean, comfortable, fully equipped apartment in the heart of Portsmouth. We had a wonderful stay and we absolutely love Portsmouth. We will definitely be back for another stay! "
United States
Sabra G.
The price is €318
includes taxes & fees
26 Oct - 27 Oct
Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ
A room with a wooden floor, a sofa, a table, and a window with curtains.

8. 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 €327
includes taxes & fees
27 Oct - 28 Oct
Great Island Inn - King Studio Apt - Main Street View
A covered porch with a table and chair, a white railing, and large windows.

9. The Deck Downtown | Walk 2 Downtown | Washer/Dryer

The Deck Downtown | Walk 2 Downtown | Washer/Dryer
West End
The price is €434
includes taxes & fees
26 Oct - 27 Oct
The Deck Downtown | Walk 2 Downtown | Washer/Dryer
An outdoor seating area with tables and chairs, a metal railing, and a view of buildings in the background.

10. Treadwell Mansion

Treadwell Mansion
4.0 star property
Downtown
9.4 out of 10, Exceptional, (24 reviews)
"Great location, easy check in. Love the property and the room had everything we needed, just wished our stay was longer!"
United States
Judith
The price is €270
includes taxes & fees
24 Nov - 25 Nov
Treadwell Mansion
A deck with wicker furniture and a table, surrounded by a white railing.

11. 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.
Harbor Serenity | Private Deck | Mins to Beach
A swimming pool with lounge chairs and a covered area, surrounded by trees and a building in the background.

12. 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
Pink Blossom Family Resort
A large estate with a main house, a pond, and a well-maintained lawn.

13. Spacious 2BR York Retreat w/ Big Backyard

Spacious 2BR York Retreat w/ Big Backyard
York
The price is €178
includes taxes & fees
26 Oct - 27 Oct
Spacious 2BR York Retreat w/ Big Backyard
A dining table with a tray holding a bottle of wine, two glasses, and a salt shaker.

14. 2-Bedroom Apt Near UNH, Portsmouth! - Parking, Full Kitchen, Free Wine!

2-Bedroom Apt Near UNH, Portsmouth! - Parking, Full Kitchen, Free Wine!
Dover
7.6 out of 10, Good, (5 reviews)
"The apartment was perfect for my little family of four which consists of myself, my husband and our 1 and 5 year old children. Perfect size, price and location. "
United States
Jessica F.
The price is €240
includes taxes & fees
5 Nov - 6 Nov
2-Bedroom Apt Near UNH, Portsmouth! - Parking, Full Kitchen, Free Wine!
A bedroom with a bed, a dresser, a television, and a hallway leading to a dining area.

15. Spacious Comfy 1-Bedroom Apt ~ Dover / Portsmouth ~ Free Wine ~ AC / Heat

Spacious Comfy 1-Bedroom Apt ~ Dover / Portsmouth ~ Free Wine ~ AC / Heat
Dover
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and comfortable for 3 of us. They supplied a blow up mattress but the sofa was just fine. Walkable to shops taverns restaurants and ice cream. Convenient drive to Portsmouth. Amtrak is a short walk away."
United States
lori
Spacious Comfy 1-Bedroom Apt ~ Dover / Portsmouth ~ Free Wine ~ AC / Heat
A living room with a grey sofa, a wooden coffee table, and a TV on a wooden stand.

16. 2-Bedroom Apt - Dover/Portsmouth

2-Bedroom Apt - Dover/Portsmouth
Dover
9.6 out of 10, Exceptional, (28 reviews)
"Very cute old house converted into apartments. It was very nice to have the space to spread out. Communication with the owners was easy and helpful."
United States
Melinda
2-Bedroom Apt - Dover/Portsmouth
The Perch`s living room

17. The Perch on Penhallow, Downtown Portsmouth

The Perch on Penhallow, Downtown Portsmouth
Downtown
9.8 out of 10, Exceptional, (15 reviews)
"Our hosts were extremely accommodating. We had a wonderful stay. Great place in a great location."
United States
Susan G.
The price is €336
includes taxes & fees
17 Nov - 18 Nov
The Perch on Penhallow, Downtown Portsmouth
A modern kitchen with wooden flooring, white cabinetry, a central island with stools, and a view of the outdoors through large windows.

18. 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 €371
includes taxes & fees
27 Oct - 28 Oct
Bright Bungalow, King-size Bed, Fence-in Backyard–Cool, Cozy & Dog Friendly
A deck with outdoor furniture, including sofas and a table, and large windows on the house.

19. 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.
The price is €365
includes taxes & fees
26 Oct - 27 Oct
Serenity @ Snug Harbor | Ocean View | Private Deck
A hotel room with a large window overlooking a harbor, a marble table, and a bottle of champagne.

20. Tugboat Vista 2 Bedroom Downtown Portsmouth

Tugboat Vista 2 Bedroom Downtown Portsmouth
Downtown
10.0 out of 10, Exceptional, (18 reviews)
"Charming clean property in outstanding location. Above fantastic shops in downtown Portsmouth! Eateries snd boutiques only a short walk away!"
United States
Charlotte C.
The price is €318
includes taxes & fees
2 Nov - 3 Nov
Tugboat Vista 2 Bedroom Downtown 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.
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Top Kittery Hotel Reviews

Hampton Inn & Suites Kittery-Portsmouth

Hampton Inn & Suites Kittery-Portsmouth

8/10 Good
"Worked out great to stay here! The staff were welcoming, the breakfast was very good with multiple choices of things to eat and the room was comfortable. We appreciated the full length mirror in the room along with other mirrors so everyone could get ready for the day easily. The location was perfect to have easy access to all the surrounding areas and places to eat nearby."
Cheryl 4-night trip
Posted 2 hours ago
Hampton Inn & Suites Kittery-Portsmouth

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, apart-hotels, 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 €94 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.

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.