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 $193
CA $290 total
includes taxes & fees
Sep 7 - Sep 8
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, (120 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 $276
CA $348 total
includes taxes & fees
Sep 3 - Sep 4
Great Island Inn

3. Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore

Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore
Downtown
10.0 out of 10, Exceptional, (71 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 $227
CA $560 total
includes taxes & fees
Sep 7 - Sep 8
Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore

4. 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 $285
CA $592 total
includes taxes & fees
Aug 30 - Aug 31
Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ

5. Treadwell Mansion

Treadwell Mansion
4.0 star property
Downtown
9.6 out of 10, Exceptional, (4 reviews)
"It was superb. Best hotel I’ve stayed in"
United States
Marlena
The price is CA $418
CA $454 total
includes taxes & fees
Sep 28 - Sep 29
Treadwell Mansion

6. Market Street Loft in Historic Downtown Portsmouth

Market Street Loft in Historic Downtown Portsmouth
Downtown
9.8 out of 10, Exceptional, (26 reviews)
"Great place to stay! Just be prepared for a lot of stairs."
United States
grace o.
The price is CA $248
CA $478 total
includes taxes & fees
Sep 1 - Sep 2
Market Street Loft in Historic Downtown Portsmouth

7. Downtown Portsmouth 2 Bedroom 2 King Beds

Downtown Portsmouth 2 Bedroom 2 King Beds
Downtown
9.6 out of 10, Exceptional, (11 reviews)
"Very clean space. Host was extremely fast to respond to any questions/issues. Location was perfect…walk out door to explore downtown Portsmouth. "
United States
Kelley G.
The price is CA $166
CA $408 total
includes taxes & fees
Aug 30 - Aug 31
Downtown Portsmouth 2 Bedroom 2 King Beds

8. 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 $366
CA $623 total
includes taxes & fees
Sep 2 - Sep 3
The Perch on Penhallow, Downtown Portsmouth

9. Tugboat Vista 2 Bedroom Downtown Portsmouth

Tugboat Vista 2 Bedroom Downtown Portsmouth
Downtown
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful apartment in a great location!"
United States
Marshall C.
The price is CA $400
CA $664 total
includes taxes & fees
Sep 22 - Sep 23
Tugboat Vista 2 Bedroom Downtown Portsmouth

10. 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 $276
CA $540 total
includes taxes & fees
Sep 28 - Sep 29
West-End Gem 2BR Live like a Local in Portsmouth

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

Serenity @ Snug Harbor | Ocean View | Private Deck
Rye
9.8 out of 10, Exceptional, (23 reviews)
"Great place and responsive host"
United States
Mickie G.
The price is CA $364
CA $769 total
includes taxes & fees
Aug 31 - Sep 1
Serenity @ Snug Harbor | Ocean View | Private Deck

12. "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 $233
CA $591 total
includes taxes & fees
Sep 2 - Sep 3
"The Surf" | Ocean & Marsh Views | Rooftop Deck

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

😊Cozy Downtown🍷FreeWine🍷10min to Portsmouth/UNH🚘
Dover
9.4 out of 10, Exceptional, (24 reviews)
"Great stay, my wife and I loved it there!"
United States
noah y.
The price is CA $187
CA $416 total
includes taxes & fees
Sep 11 - Sep 12
😊Cozy Downtown🍷FreeWine🍷10min to Portsmouth/UNH🚘

14. 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 $188
CA $307 total
includes taxes & fees
Aug 31 - Sep 1
Vintage Glamper Oasis in Downtown Dover, walk to downtown and Henry Law Park

15. Chic Loft-Style Condo in Downtown Portsmouth

Chic Loft-Style Condo in Downtown Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Reminder that there is no oven/stove so plan accordingly."
United Kingdom
Anonymous traveller
The price is CA $427
CA $789 total
includes taxes & fees
Sep 15 - Sep 16
Chic Loft-Style Condo in Downtown Portsmouth

16. Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻‍🎓

Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻‍🎓
Newmarket
9.2 out of 10, Wonderful, (29 reviews)
"Great place to stay! Very clean and cozy, plenty of parking and in a quiet area. Communication with the host was easy and prompt. Highly recommend this place. "
United States
Amanda C.
Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻‍🎓

17. The Nest-Cozy Retreat Near Portsmouth +Ogunquit, Full kitchen, close to every...

The Nest-Cozy Retreat Near Portsmouth +Ogunquit, Full kitchen, close to every...
York
10.0 out of 10, Exceptional, (9 reviews)
"Enjoyed my stay, great place and location. Bedroom fan wasn’t working so it was a little unbearable for 2 days. Other than that would definitely stay there again!"
United States
Stephanie B.
The price is CA $188
CA $437 total
includes taxes & fees
Aug 30 - Aug 31
The Nest-Cozy Retreat Near Portsmouth +Ogunquit, Full kitchen, close to every...

18. Pink Blossom Family Resort

Pink Blossom Family Resort
3.0 star property
Ogunquit
9.6 out of 10, Exceptional, (317 reviews)
"Always a great stay immaculately clean, super friendly staff and great location!"
United States
Donna
The price is CA $193
CA $217 total
includes taxes & fees
Sep 28 - Sep 29
Pink Blossom Family Resort

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 $499
CA $734 total
includes taxes & fees
Sep 2 - Sep 3
The Penthouse at Penhallow
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?

New build. 3 bedroom Townhouse walking distance to York Beaches.: This vacation home rental near Kittery is equipped with a selection of games, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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.