Cundys Harbor Holiday Rentals

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Our top choices for Cundys Harbor holiday rentals

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (7)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
United States
Melanie L.
The price is NZ$343
includes taxes & fees
28 Dec - 29 Dec
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.
Boothbay
10.0 out of 10, Exceptional, (1)
"This efficiency apartment was nicely furnished with everything needed and conveniently located on the main road into Boothbay Harbor. The host was generous and accommodating. The region is fun to visit!"
United States
Mary D.
The price is NZ$478
includes taxes & fees
29 Dec - 30 Dec
Queen non smoking efficiency, free parking in beautiful Boothbay,Maine.

Modern, luxurious cabin in the woods - 21

Modern, luxurious cabin in the woods - 21
Freeport
10.0 out of 10, Exceptional, (1)
The price is NZ$510
includes taxes & fees
28 Dec - 29 Dec
Modern, luxurious cabin in the woods - 21

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (145)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is NZ$205
includes taxes & fees
18 Jan - 19 Jan 2026
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Escape to Positive Outlook

Escape to Positive Outlook
West Point
10.0 out of 10, Exceptional, (3)
"The host was welcoming. The home was clean, comfortable and the views were outstanding. "
United States
Rachel K.
The price is NZ$325
includes taxes & fees
4 Jan - 5 Jan 2026
Escape to Positive Outlook

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is NZ$452
includes taxes & fees
1 Jan - 2 Jan 2026
Brunswick Downtown Sugar Cube next to Bowdoin

Top floor loft apartment in downtown Bath

Top floor loft apartment in downtown Bath
Bath
9.8 out of 10, Exceptional, (6)
"Awesome location, great stay, loved the apartment"
United States
William B.
The price is NZ$379
includes taxes & fees
4 Jan - 5 Jan 2026
Top floor loft apartment in downtown Bath

Solitude @ The Offshore House

Solitude @ The Offshore House
Boothbay
9.8 out of 10, Exceptional, (7)
"Managers were very responsive and helpful. Condo was very clean and comfortable and close to the town of Boothbay Harbor and Ocean Point and the Botanic Gardens. "
United States
Linda O.
The price is NZ$516
includes taxes & fees
28 Dec - 29 Dec
Solitude @ The Offshore House

Tiny A-Frame Romantic Getaway

Tiny A-Frame Romantic Getaway
Wiscasset
10.0 out of 10, Exceptional, (3)
"Very nice and very quiet "
United States
justin s.
The price is NZ$594
includes taxes & fees
21 Jan - 22 Jan 2026
Tiny A-Frame Romantic Getaway

Seabed @ The Offshore House

Seabed @ The Offshore House
Boothbay
9.8 out of 10, Exceptional, (14)
"Our room was excellent!!! Everything was clean and organized and looked beautiful. Location was just far enough from all the attractions to make it very comfortable. Will definitely return next time we are in the area. "
United States
Steve G.
The price is NZ$516
includes taxes & fees
29 Dec - 30 Dec
Seabed @ The Offshore House

Historic Bath's, Home Away from Home

Historic Bath's, Home Away from Home
Bath
The price is NZ$500
includes taxes & fees
1 Jan - 2 Jan 2026
Historic Bath's, Home Away from Home

Studio Apartment in Freeport

Studio Apartment in Freeport
2.0 star property
Freeport
The price is NZ$258
includes taxes & fees
5 Jan - 6 Jan 2026
Studio Apartment in Freeport

Shipwright @ The Offshore House

Shipwright @ The Offshore House
Boothbay
9.6 out of 10, Exceptional, (14)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
The price is NZ$516
includes taxes & fees
3 Jan - 4 Jan 2026
Shipwright @ The Offshore House

Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!

Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!
Bath
8.6 out of 10, Excellent, (10)
"Nice, clean, cosy, conveniently located and easy enough to find. Great communication with host, comfortable beds and plenty of hot water. very responsive and would definitely consider using again. "
United States
A M.
Experience the magic of Captain's 2BR Winter Retreat, experience best of Bath!

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is NZ$426
includes taxes & fees
5 Jan - 6 Jan 2026
2King Bed BR Private Apt Downtown Brunswick

Fred Cottage - Spacious retreat on Popham Beach!

Fred Cottage - Spacious retreat on Popham Beach!
Phippsburg
9.0 out of 10, Wonderful, (2)
"Off the beaten path, easy access to beach and Spinneys"
United States
Sean B.
The price is NZ$375
includes taxes & fees
5 Jan - 6 Jan 2026
Fred Cottage - Spacious retreat on Popham Beach!

Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.0 out of 10, Very good, (4)
"We really enjoyed our stay on Bailey Island. The apartment was clean and comfortable. The kitchen was well stocked and former renters had even left some food in the fridge.The house is in a sweet little, quiet community. Would recommend. Thanks"
United States
Reen and Gordon H.
The price is NZ$396
includes taxes & fees
28 Dec - 29 Dec
Sunset Hideaway on Bailey Island

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is NZ$441
includes taxes & fees
25 Jan - 26 Jan 2026
Little Lincoln beautiful home

Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (14)
"The views are amazing! A very relaxing place to be, and the house was clean and comfortable. "
United States
Monika G.
The price is NZ$527
includes taxes & fees
12 Jan - 13 Jan 2026
Fantastic Waterfront Views

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is NZ$841
includes taxes & fees
31 Dec - 1 Jan 2026
Beautiful 3BR Home with Office in Town of Brunswick with King beds
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 out more about Cundys Harbor

Everything you need to know about Cundys Harbor 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 Cundys Harbor 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 Cundys Harbor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cundys Harbor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cundys Harbor. 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 Cundys Harbor 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 Cundys Harbor holiday rentals we have selected for you start as low as NZ$527 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cundys Harbor rentals

At Expedia, we put the best Cundys Harbor 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 Cundys Harbor 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 Cundys Harbor 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 Cundys Harbor. 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 holiday rentals in Cundys Harbor?

Yes, there are holiday rentals close to the most popular sights in Cundys Harbor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cundys Harbor has to offer?

8mn to Gardens Aglow! Peaceful Lake! Automatic Generator! Full Kitchen! Heat! : This holiday home rental outside of Cundys Harbor is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Cundys Harbor?

While exploring the area, visit family-friendly sights like Boothbay Railway Village, or get outside and enjoy nature at Popham Beach. In the wider area, you’ll find Bailey Island Bridge and Popham Beach State Park.

What are holiday rentals like in Cundys Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cundys Harbor. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family getaway.