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

Kittery Vacation Rentals

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Our top choices for Kittery vacation 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 CA $167
CA $261 total
includes taxes & fees
Sep 20 - Sep 21
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 CA $274
CA $347 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $223
CA $559 total
includes taxes & fees
Sep 13 - Sep 14
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 CA $147
CA $302 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $227
CA $521 total
includes taxes & fees
Sep 16 - Sep 17
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 price is CA $280
CA $650 total
includes taxes & fees
Sep 13 - Sep 14
"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 CA $298
CA $574 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $399
CA $665 total
includes taxes & fees
Sep 22 - Sep 23
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 CA $431
CA $468 total
includes taxes & fees
Oct 8 - Oct 9
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 CA $356
CA $701 total
includes taxes & fees
Sep 15 - Sep 16
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 CA $187
CA $305 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $228
CA $488 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $434
CA $702 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $200
CA $1,140 total
includes taxes & fees
Sep 22 - Sep 23
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 CA $127
CA $596 total
includes taxes & fees
Sep 17 - Sep 18
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 CA $207
CA $248 total
includes taxes & fees
Sep 21 - Sep 22
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 price is CA $1,228
CA $1,546 total
includes taxes & fees
Oct 3 - Oct 4
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 CA $186
CA $210 total
includes taxes & fees
Oct 4 - Oct 5
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kittery. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there vacation rentals in Kittery?

Yes, you can find vacation rentals in Kittery near Yummies Candy and Nuts, or you can select a secluded option if you'd like a relaxing place to 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 vacation home rentals that Kittery has to offer?

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

How many vacation rentals are there in Kittery?

Choose from 20 Expedia vacation rentals in Kittery for a memorable vacation.

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 larger area, you’ll find popular places like Hampton Beach and Ogunquit Beach.

What are vacation rentals like in Kittery?

Vacation rentals are privately owned accommodations you can reserve for several days or longer in Kittery. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family getaway.