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. 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 CA $95
CA $250 total
includes taxes & fees
Oct 28 - Oct 29
Fresh + Modern Garden Level Kittery Studio

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 CA $128
CA $174 total
includes taxes & fees
Oct 27 - Oct 28
Rye Motor Inn - Oceanfront, Walk to Beach

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 CA $223
CA $289 total
includes taxes & fees
Oct 27 - Oct 28
Great Island Inn

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 CA $108
CA $277 total
includes taxes & fees
Oct 28 - Oct 29
Historical Apt. In Downtown Portsmouth

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 CA $173
CA $421 total
includes taxes & fees
Nov 2 - Nov 3
Downtown Portsmouth 2 Bedroom 2 King Beds

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.
The price is CA $176
CA $390 total
includes taxes & fees
Oct 29 - Oct 30
Market Street Loft in Historic Downtown Portsmouth

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 CA $201
CA $494 total
includes taxes & fees
Oct 27 - Oct 28
Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ

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 CA $279
CA $507 total
includes taxes & fees
Nov 3 - Nov 4
Great Island Inn - King Studio Apt - Main Street View

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

The Deck Downtown | Walk 2 Downtown | Washer/Dryer
West End
The price is CA $249
CA $687 total
includes taxes & fees
Oct 27 - Oct 28
The Deck Downtown | Walk 2 Downtown | Washer/Dryer

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 CA $371
CA $403 total
includes taxes & fees
Nov 3 - Nov 4
Treadwell Mansion

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.
The price is CA $224
CA $603 total
includes taxes & fees
Oct 27 - Oct 28
Harbor Serenity | Private Deck | Mins to Beach

12. Pink Blossom Family Resort

Pink Blossom Family Resort
3.0 star property
Ogunquit
9.6 out of 10, Exceptional, (330 reviews)
"It was great and a great location."
United States
Robert
Pink Blossom Family Resort

13. Spacious 2BR York Retreat w/ Big Backyard

Spacious 2BR York Retreat w/ Big Backyard
York
The price is CA $151
CA $270 total
includes taxes & fees
Oct 27 - Oct 28
Spacious 2BR York Retreat w/ Big Backyard

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 CA $109
CA $371 total
includes taxes & fees
Nov 5 - Nov 6
2-Bedroom Apt Near UNH, Portsmouth! - Parking, Full Kitchen, Free Wine!

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

16. 2-Bedroom Apt - Dover/Portsmouth

2-Bedroom Apt - Dover/Portsmouth
Dover
9.6 out of 10, Exceptional, (29 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

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 CA $282
CA $523 total
includes taxes & fees
Nov 16 - Nov 17
The Perch on Penhallow, Downtown Portsmouth

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 CA $322
CA $575 total
includes taxes & fees
Oct 27 - Oct 28
Bright Bungalow, King-size Bed, Fence-in Backyard–Cool, Cozy & Dog Friendly

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 CA $251
CA $635 total
includes taxes & fees
Oct 28 - Oct 29
Serenity @ Snug Harbor | Ocean View | Private Deck

20. Tugboat Vista 2 Bedroom Downtown Portsmouth

Tugboat Vista 2 Bedroom Downtown Portsmouth
Downtown
10.0 out of 10, Exceptional, (19 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 CA $253
CA $485 total
includes taxes & fees
Nov 2 - Nov 3
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

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?

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

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. Kittery Premium Outlets and Hampton Beach are a couple of places you'll find in the larger area.

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.