Kittery Point Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Kittery Point holiday rentals

A coastal town with a marina filled with boats, surrounded by residential buildings and a clear sky.

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 NZ$1,046
includes taxes & fees
30 Nov - 1 Dec
Amazing harbor/ocean views of Pepperrell Cove
A living room with a fireplace, a sofa, a round glass coffee table, and a patterned rug.

2. Treadwell Mansion

Treadwell Mansion
4.0 star property
Downtown
9.4 out of 10, Exceptional, (29 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 NZ$349
includes taxes & fees
10 Nov - 11 Nov
Treadwell Mansion
A wooden door with a brass anchor handle, a staircase with a patterned wall, and a window with a number "3" on the right.

3. 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 NZ$312
includes taxes & fees
10 Nov - 11 Nov
Great Island Inn
Garden

4. 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, (138 reviews)
"Great location great hotel"
United States
Elizabeth
The price is NZ$227
includes taxes & fees
15 Nov - 16 Nov
Rye Motor Inn - Oceanfront, Walk to Beach
A room with a wooden floor, a sofa, a table, and a window with curtains.

5. 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 NZ$531
includes taxes & fees
12 Nov - 13 Nov
Great Island Inn - King Studio Apt - Main Street View
A green two-story house with a central wooden door, black-framed windows, and a small porch with a railing.

6. Great Island Inn - Queen Studio Apt - Village View

Great Island Inn - Queen Studio Apt - Village View
New Castle
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time. Nicely done"
United States
michael m.
The price is NZ$487
includes taxes & fees
10 Nov - 11 Nov
Great Island Inn - Queen Studio Apt - Village View
A snow-covered street with a building featuring a 'Hello Lovely' sign.

7. 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.
Townhouse Apt 2 w Parking in Downtown Portsmouth
An outdoor seating area with brick walls and black and white photographs.

8. 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 NZ$679
includes taxes & fees
23 Nov - 24 Nov
Downtown Escape ❤️ Deck, Fireplace, 95 WalkScore
A room with a fireplace, a ceiling fan, a mirror, and a door leading to another room.

9. 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 NZ$335
includes taxes & fees
24 Nov - 25 Nov
Historical Apt. In Downtown Portsmouth
A spacious living area with a high ceiling, exposed wooden beams, a large sofa, a coffee table, and a kitchen in the background.

10. The Penthouse at Penhallow

The Penthouse at Penhallow
Downtown
10.0 out of 10, Exceptional, (17 reviews)
"Absolutely beautiful full of history in a great location "
United States
Richard H.
The price is NZ$734
includes taxes & fees
11 Nov - 12 Nov
The Penthouse at Penhallow
The Perch`s living room

11. 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 NZ$581
includes taxes & fees
2 Dec - 3 Dec
The Perch on Penhallow, Downtown Portsmouth
A marina with boats, a large tent, and outdoor seating areas.

12. 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 NZ$322
includes taxes & fees
22 Nov - 23 Nov
Fresh + Modern Garden Level Kittery Studio
A covered porch with a table and chair, a white railing, and large windows.

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

The Deck Downtown | Walk 2 Downtown | Washer/Dryer
West End
The Deck Downtown | Walk 2 Downtown | Washer/Dryer
A wooden deck with outdoor seating, string lights, and a brick wall.

14. 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 NZ$643
includes taxes & fees
29 Nov - 30 Nov
Market Street Loft in Historic Downtown Portsmouth
A bedroom with a large bed, two bedside lamps, a ceiling light, a skylight, a wooden dresser, and a mirror on the wall.

15. 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 NZ$560
includes taxes & fees
10 Dec - 11 Dec
Downtown Portsmouth 2 Bedroom 2 King Beds
A modern living room with a brown leather sofa, two armchairs, a coffee table, and a flat-screen TV mounted on the wall.

16. 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.
Speakeasy Vibe ~ Luxe 1BR ~ <2min walk to MKT SQ
A hotel room with a large window overlooking a harbor, a marble table, and a bottle of champagne.

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 NZ$610
includes taxes & fees
2 Dec - 3 Dec
Tugboat Vista 2 Bedroom Downtown Portsmouth
A kitchen with a wooden table, chairs, a refrigerator, and a window with blinds.

18. King Bed | Downtown Suite | Port City Stays

King Bed | Downtown Suite | Port City Stays
Downtown
9.4 out of 10, Exceptional, (9 reviews)
"This property was in a great location, had ample parking options and was easily accessible. The property was clean, cute and had everything we needed for our stay. Appreciated the well stocked coffee bar! "
United States
Elizabeth H.
King Bed | Downtown Suite | Port City Stays
A deck with wicker furniture and a table, surrounded by a white railing.

19. 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.
Harbor Serenity | Private Deck | Mins to Beach
A cozy living area with a round table, wicker chairs, a sofa, and a TV stand.

20. 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
Chic Loft-Style Condo 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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Find holiday rentals that suit your style

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Top Kittery Point Hotel Reviews

An outdoor patio with a fire pit, seating, and a restaurant view.
Home2 Suites By Hilton Kittery

Home2 Suites By Hilton Kittery

Home2 Suites By Hilton Kittery
Kittery

8/10 Good

Pros: Good beds Great to have a little kitchen in the room Breakfast was great Cons: Terrible noise insulation! The first few nights were fine, and then the last night it sounded like toddlers were wrestling in the room above us at 2am, the room next to us played music we could hear, and there was yelling in the hallway partway through the night. It took it from the best hotel experience we’ve had to the worst.
Australia
Katherine
Reviewed October 25, 2026
Home2 Suites By Hilton Kittery

Find out more about Kittery Point

Everything you need to know about Kittery Point 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 Point holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Point holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kittery Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kittery Point. 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 Point 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 Point holiday rentals we have selected for you start as low as NZ$227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kittery Point rentals

At Expedia, we put the best Kittery Point 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 Point 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 Point 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 Point. 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

Can I find a holiday rental in Kittery Point?

Yes, there are holiday rentals close to the most popular sights in Kittery Point, or you can select a more 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 holiday rentals that Kittery Point has to offer?

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

How many holiday rentals are there in Kittery Point?

Expedia has 16 holiday 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 wider area.

What are holiday rentals like in Kittery Point?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kittery Point. Holiday rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family trips or small group gatherings.