An aerial view of a coastal area with a bridge connecting two landmasses, surrounded by dense forests and a large body of water.

Kittery Point Vacation Rentals

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Our top choices for Kittery Point vacation rentals

1. Amazing harbor/ocean views of Pepperrell Cove

Amazing harbor/ocean views of Pepperrell Cove
Kittery
10.0 out of 10, Exceptional, (34 reviews)
"They thought of everything in this house. We loved it. All the rooms have a beautiful view, and the location was very convenient."
United States
Rachel F.
The price is CA $358
CA $796 total
includes taxes & fees
Dec 2 - Dec 3
Amazing harbor/ocean views of Pepperrell Cove

2. Great Island Inn

Great Island Inn
3.5 star property
New Castle
10.0 out of 10, Exceptional, (130 reviews)
"Fantastic location, beautiful views it’s a gem on the island!"
United States
Craig
The price is CA $180
CA $242 total
includes taxes & fees
Nov 4 - Nov 5
Great Island Inn

3. Treadwell Mansion

Treadwell Mansion
4.0 star property
Downtown
9.4 out of 10, Exceptional, (27 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 $204
CA $221 total
includes taxes & fees
Nov 11 - Nov 12
Treadwell Mansion

4. 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, (135 reviews)
"Amazing stay and place"
United States
Amanda
The price is CA $111
CA $155 total
includes taxes & fees
Nov 4 - Nov 5
Rye Motor Inn - Oceanfront, Walk to Beach

5. 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 $58
CA $196 total
includes taxes & fees
Nov 6 - Nov 7
Fresh + Modern Garden Level Kittery Studio

6. 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 $208
CA $394 total
includes taxes & fees
Nov 4 - Nov 5
Great Island Inn - King Studio Apt - Main Street View

7. Historical Apt. In Downtown Portsmouth

Historical Apt. In Downtown Portsmouth
West End
10.0 out of 10, Exceptional, (5 reviews)
"The property is just as advertised and is a very nice place to stay. Very convenient to attractions and places to eat. Ample off street parking. Would definitely stay here again."
United States
Robert C.
The price is CA $118
CA $276 total
includes taxes & fees
Nov 4 - Nov 5
Historical Apt. In Downtown Portsmouth

8. Spacious 2BR York Retreat w/ Big Backyard

Spacious 2BR York Retreat w/ Big Backyard
York
The price is CA $78
CA $180 total
includes taxes & fees
Nov 8 - Nov 9
Spacious 2BR York Retreat w/ Big Backyard

9. 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 $226
CA $621 total
includes taxes & fees
Nov 18 - Nov 19
Harbor Serenity | Private Deck | Mins to Beach

10. 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 $156
CA $379 total
includes taxes & fees
Nov 4 - Nov 5
Downtown Portsmouth 2 Bedroom 2 King Beds

11. The Penthouse at Penhallow

The Penthouse at Penhallow
Downtown
10.0 out of 10, Exceptional, (17 reviews)
"Great location. Kitchen was well stocked. Beds were comfortable and bathrooms nice. Will rent again."
United States
Kimberlee
The price is CA $300
CA $518 total
includes taxes & fees
Nov 4 - Nov 5
The Penthouse at Penhallow

12. 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 $233
CA $506 total
includes taxes & fees
Nov 4 - Nov 5
Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ

13. Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore

Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore
Downtown
10.0 out of 10, Exceptional, (73 reviews)
"Great space and wonderful location!!"
United States
Madeline A.
The price is CA $239
CA $528 total
includes taxes & fees
Nov 23 - Nov 24
Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore

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

The Deck Downtown | Walk 2 Downtown | Washer/Dryer
West End
The price is CA $296
CA $836 total
includes taxes & fees
Nov 8 - Nov 9
The Deck Downtown | Walk 2 Downtown | Washer/Dryer

15. 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 $286
CA $502 total
includes taxes & fees
Nov 29 - Nov 30
Market Street Loft in Historic Downtown Portsmouth

16. 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 $241
CA $450 total
includes taxes & fees
Nov 8 - Nov 9
The Perch on Penhallow, Downtown Portsmouth

17. 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 $291
CA $506 total
includes taxes & fees
Nov 22 - Nov 23
Tugboat Vista 2 Bedroom 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 $336
CA $563 total
includes taxes & fees
Nov 15 - Nov 16
Bright Bungalow, King-size Bed, Fence-in Backyard–Cool, Cozy & Dog Friendly

19. Chic Loft-Style Condo in Downtown Portsmouth

Chic Loft-Style Condo in Downtown Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay. Reminder that there is no oven/stove so plan accordingly."
United Kingdom
Anonymous traveller
The price is CA $266
CA $561 total
includes taxes & fees
Nov 17 - Nov 18
Chic Loft-Style Condo in Downtown Portsmouth

20. Townhouse Apt 2 w Parking in Downtown Portsmouth

Townhouse Apt 2 w Parking in Downtown Portsmouth
Downtown
10.0 out of 10, Exceptional, (2 reviews)
"great place in a great location!"
United States
Ryan F.
The price is CA $454
CA $535 total
includes taxes & fees
Nov 22 - Nov 23
Townhouse Apt 2 w Parking in 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 Point Hotel Reviews

Find out more about Kittery Point

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 Point. 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.

Frequently asked questions

Can I find a vacation rental in Kittery Point?

Yes, we give you a choice of vacation rentals near popular attractions in Kittery Point, or you can go with a secluded option if you're looking for a relaxing stay. Kittery Point is known for its seaside and seafood restaurants.

What are some of the best vacation home rentals in Kittery Point?

STUNNING BEACHSIDE HOME-WELLS BEACH: 180 DEGREE OCEAN VIEWS: 9-1 to 9-3 open: Visitors like this Kittery Point vacation home rental. It 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 Point?

Expedia has 16 vacation rentals for your stay in Kittery Point.

What can I see and do in Kittery Point?

Explore the area and family-friendly sights such as Water Country, or get out into nature at a spot like Hampton Beach. Fort McClary State Park and Prescott Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Kittery Point?

Vacation rentals are private properties you can reserve for several days or more in Kittery Point. Vacation rentals offer extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.