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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Our top choices for Kittery holiday rentals

1. 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, (116 reviews)
"Amazing stay and place"
United States
Amanda
The price is €163
includes taxes & fees
14 Sept - 15 Sept
Rye Motor Inn - Oceanfront, Walk to Beach

2. Great Island Inn

Great Island Inn
3.5 star property
New Castle
10.0 out of 10, Exceptional, (122 reviews)
"The room was very clean, decorated beautifully, and had great walkability. The bed was very comfy and had all the things you might need like kitchen and bathroom items. We wished we could stay longer!"
United States
Jennifer
The price is €216
includes taxes & fees
13 Sept - 14 Sept
Great Island Inn

3. Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore

Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore
Downtown
10.0 out of 10, Exceptional, (72 reviews)
"Very convenient location. In the heart of Portsmouth's historic area - restaurants, shopping, points of interest, and arts/entertainment sites. Excellent place for two with large kitchen area."
United States
Martin S.
The price is €344
includes taxes & fees
13 Sept - 14 Sept
Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore

4. Historical Apt. In Downtown Portsmouth

Historical Apt. In Downtown Portsmouth
West End
10.0 out of 10, Exceptional, (4 reviews)
The price is €207
includes taxes & fees
29 Sept - 30 Sept
Historical Apt. In Downtown Portsmouth

5. 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, (10 reviews)
"Very conveniently located and comfortable property in the heart of Portsmouth."
United States
Emily B.
The price is €332
includes taxes & fees
16 Sept - 17 Sept
Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ

6. "The Surf" | Ocean & Marsh Views | Rooftop Deck

"The Surf" | Ocean & Marsh Views | Rooftop Deck
Rye
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful location. All we could ask for."
United States
chris c.
"The Surf" | Ocean & Marsh Views | Rooftop Deck

7. Downtown Portsmouth 2 Bedroom 2 King Beds

Downtown Portsmouth 2 Bedroom 2 King Beds
Downtown
9.4 out of 10, Exceptional, (12 reviews)
"Nice little VRBO for a quick stay. Beds were comfortable, clean uncluttered layout, close to everything."
United States
Tim B.
The price is €365
includes taxes & fees
30 Sept - 1 Oct
Downtown Portsmouth 2 Bedroom 2 King Beds

8. 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

9. Tugboat Vista 2 Bedroom Downtown Portsmouth

Tugboat Vista 2 Bedroom Downtown Portsmouth
Downtown
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful apartment in a great location!"
United States
Marshall C.
The price is €422
includes taxes & fees
22 Sept - 23 Sept
Tugboat Vista 2 Bedroom Downtown Portsmouth

10. Treadwell Mansion

Treadwell Mansion
4.0 star property
Downtown
8.4 out of 10, Very good, (6 reviews)
"It was superb. Best hotel I’ve stayed in"
United States
Marlena
The price is €295
includes taxes & fees
15 Sept - 16 Sept
Treadwell Mansion

11. 😊Cozy Downtown🍷FreeWine🍷10min to Portsmouth/UNH🚘

😊Cozy Downtown🍷FreeWine🍷10min to Portsmouth/UNH🚘
Dover
9.4 out of 10, Exceptional, (25 reviews)
"Great stay, my wife and I loved it there!"
United States
noah y.
😊Cozy Downtown🍷FreeWine🍷10min to Portsmouth/UNH🚘

12. Chic Loft-Style Condo in Downtown Portsmouth

Chic Loft-Style Condo in Downtown Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Reminder that there is no oven/stove so plan accordingly."
United Kingdom
Anonymous traveller
The price is €434
includes taxes & fees
15 Sept - 16 Sept
Chic Loft-Style Condo in Downtown Portsmouth

13. Vintage Glamper Oasis in Downtown Dover, walk to downtown and Henry Law Park

Vintage Glamper Oasis in Downtown Dover, walk to downtown and Henry Law Park
Dover
10.0 out of 10, Exceptional, (18 reviews)
"Welcoming hosts and fantastic little place to stay. Walking distance to plenty of places to eat, and a great location overall."
United States
Michael R.
The price is €197
includes taxes & fees
11 Oct - 12 Oct
Vintage Glamper Oasis in Downtown Dover, walk to downtown and Henry Law Park

14. West-End Gem 2BR Live like a Local in Portsmouth

West-End Gem 2BR Live like a Local in Portsmouth
West End
10.0 out of 10, Exceptional, (11 reviews)
"The location was perfect. The downtown shopping area was a 10 minute walk. "
United States
Joe T.
The price is €301
includes taxes & fees
30 Sept - 1 Oct
West-End Gem 2BR Live like a Local in Portsmouth

15. 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 price is €442
includes taxes & fees
29 Sept - 30 Sept
The Perch on Penhallow, Downtown Portsmouth

16. Low Tide - Heart of Hampton Beach!

Low Tide - Heart of Hampton Beach!
Hampton Beach
10.0 out of 10, Exceptional, (2 reviews)
"This is my spouse & I’s 2nd time going through Manie & Leslie to stay over for the holiday weekend for our deep sea fishing trip & to visit some family!! They’re amazing hosts!! Always checking in to make sure you’re having a good visit & that your stay with them is going ok!!! Such an adorable cottage *cutest decor*, very clean & within walking distance to the beach/Hampton beach strip.We had such an amazing time & can’t wait to book another trip with them!!"
United States
Bryden S.
The price is €706
includes taxes & fees
15 Sept - 16 Sept
Low Tide - Heart of Hampton Beach!

17. Walk to Public Beach Access! Breezy Hampton Condo

Walk to Public Beach Access! Breezy Hampton Condo
3.0 star property
Hampton Beach
The price is €371
includes taxes & fees
17 Sept - 18 Sept
Walk to Public Beach Access! Breezy Hampton Condo

18. Elmwood Resort Hotel

Elmwood Resort Hotel
3.0 star property
Wells
9.4 out of 10, Exceptional, (451 reviews)
"Loved the pool, great atmosphere and check-in was so smooth and easy"
United States
Dawna
The price is €155
includes taxes & fees
21 Sept - 22 Sept
Elmwood Resort Hotel

19. The Penthouse at Penhallow

The Penthouse at Penhallow
Downtown
10.0 out of 10, Exceptional, (15 reviews)
"Great location. Kitchen was well stocked. Beds were comfortable and bathrooms nice. Will rent again."
United States
Kimberlee
The Penthouse at Penhallow

20. Pink Blossom Family Resort

Pink Blossom Family Resort
3.0 star property
Ogunquit
9.6 out of 10, Exceptional, (321 reviews)
"Spacious and very clean. Super convenient to everything!"
United States
Donna
The price is €131
includes taxes & fees
4 Oct - 5 Oct
Pink Blossom Family Resort
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

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 €121 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?

Hampton Beach Seaside Villa Unit 1: This holiday home rental outside of Kittery is on the beach, and equipped with air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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. 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.