Cundys Harbor Vacation Rentals

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Check prices for these dates

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

Our top choices for Cundys Harbor vacation rentals

A two-story house with a covered porch, a garage, and a front yard with potted plants.

1. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
The price is CA $135
CA $165 total
includes taxes & fees
Nov 22 - Nov 23
Large suite/private bath/private entrance on quiet street near Thomas Bay
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (12 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is CA $149
CA $287 total
includes taxes & fees
Nov 16 - Nov 17
Mid Coast Getaway w/ water views
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

3. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
9.0 out of 10, Wonderful, (8 reviews)
"The views from the home were amazing! The home was cozy and had everything we needed for our stay. The host was great with communication and quick to reply. We were very happy with our stay and are grateful for the ability to stay here."
United States
Elizabeth M.
The price is CA $111
CA $266 total
includes taxes & fees
Nov 17 - Nov 18
Sunset Hideaway on Bailey Island
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

4. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
9.8 out of 10, Exceptional, (7 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is CA $186
CA $322 total
includes taxes & fees
Nov 17 - Nov 18
2 bedroom w/ expansive water views
A narrow hallway with a window on the right, leading to a room with a visible door.

5. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (14 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
The price is CA $142
CA $297 total
includes taxes & fees
Nov 15 - Nov 16
Modern style in historic building in downtown Bath
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is CA $174
CA $496 total
includes taxes & fees
Nov 17 - Nov 18
Mere Point Sunrise Views at Eastern Shore!
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

7. Orchid Harbor, Bailey Island 3BR

Orchid Harbor, Bailey Island 3BR
Harpswell
10.0 out of 10, Exceptional, (13 reviews)
"Lovely property, close to what we needed and wanted, host communicated promptly. Would definitely stay there again."
United States
Jane D.
The price is CA $245
CA $577 total
includes taxes & fees
Nov 16 - Nov 17
Orchid Harbor, Bailey Island 3BR
A treehouse with a wooden staircase and a small building with a colorful mural.

8. 1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!

1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is CA $170
CA $252 total
includes taxes & fees
Nov 24 - Nov 25
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

9. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
8.8 out of 10, Excellent, (3 reviews)
"Such a beautiful stay!! My whole group wished we could have stayed longer. We plan to come back"
United States
Holly G.
The price is CA $218
CA $394 total
includes taxes & fees
Nov 15 - Nov 16
Captains Watch: A Coastal Escape
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

10. Bird Watching Paradise @ Waterfront Harpswell with Private Deck

Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Harpswell
10.0 out of 10, Exceptional, (3 reviews)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
The price is CA $220
CA $458 total
includes taxes & fees
Nov 15 - Nov 16
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

11. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (24 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is CA $223
CA $399 total
includes taxes & fees
Nov 15 - Nov 16
Fantastic Waterfront Views
A wooden staircase with a wooden railing, surrounded by green foliage.

12. 1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.

1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is CA $184
CA $268 total
includes taxes & fees
Nov 27 - Nov 28
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

13. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (19 reviews)
"The place was clean, bright, and exactly as shown in the pictures. There were fresh towels (4), toiletries, dishsoap/dishwasher tablets, and an in window AC. The table and bed are both lovely and roomy for two people. Plenty of places to plug in devices. The Seadog brewery was walking distance and would recommend for dinner and a pint. Also enjoyed Dutchman's bagels and Baked on Main (marginally longer walk). We were really happy with our stay!"
United States
Stefanie M.
The price is CA $135
CA $298 total
includes taxes & fees
Nov 15 - Nov 16
King Size Sun Rise Midcoast Lovely Stay
A living room with a sofa, a coffee table, a TV, a fireplace, and a kitchen area.

14. 1st FL Downtown Grand Brunswick

1st FL Downtown Grand Brunswick
Brunswick
10.0 out of 10, Exceptional, (2 reviews)
"Great location, one block off main street, 4 or 5 blocks from grocery store."
United States
william h.
The price is CA $156
CA $384 total
includes taxes & fees
Nov 18 - Nov 19
1st FL Downtown Grand Brunswick
A spacious kitchen with a large island, bar stools, and a dining area with a sofa.

15. King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer

King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
Topsham
9.6 out of 10, Exceptional, (8 reviews)
"Perfect place and location for visiting Bowdoin."
United States
Kristen S.
The price is CA $142
CA $340 total
includes taxes & fees
Nov 16 - Nov 17
King size Bed Big Smile Big Sunshine 1st FL Washer&Dryer
A spacious living room with a wooden staircase, a dining area with chairs, and a cozy seating area with a plaid sofa.

16. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is CA $426
CA $756 total
includes taxes & fees
Nov 22 - Nov 23
Sweet comfy cottage on Small Point Road
A modern interior with a dining area, a living room, and a kitchen.

17. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"The bed was the most comfortable I have ever slept on! Lovely large warm open room. I appreciated the coffee/tea options, and the condiments in the fridge. There was a white noise machine in the room though we did not use it."
United States
Susan S.
The price is CA $98
CA $210 total
includes taxes & fees
Nov 16 - Nov 17
Studio Apartment in Freeport
A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.

18. Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.6 out of 10, Exceptional, (34 reviews)
"Perfect for what we needed for the week. All that was missing was some oven mitts and maybe a pair of scissors but we made it work!! Great little spot - thank you!! "
United States
Britta M.
The price is CA $234
CA $526 total
includes taxes & fees
Nov 15 - Nov 16
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
A modern apartment with a dining area featuring a round table and four chairs, a kitchen area with a bar counter, and a staircase leading to another level.

19. Apartment over shops in Bath Historic District

Apartment over shops in Bath Historic District
Bath
9.2 out of 10, Wonderful, (9 reviews)
"Very pleased with the quick responses from the host! The location couldn't be better and the quirks were more than manageable given the competitive price. Will definitely stay again with any property managed by this host!"
United States
Gerry
The price is CA $142
CA $302 total
includes taxes & fees
Nov 24 - Nov 25
Apartment over shops in Bath Historic District
A lakeside deck with a fire pit, docked boats, and a wooden railing.

20. Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
Boothbay Harbor
10.0 out of 10, Exceptional, (129 reviews)
"This place was the definition of relaxation! The access to West Harbor "Pond" (it's huge -- more like a lake!) was unbeatable! We were able to use the provided kayaks to explore the little islands in the water and to come really close to a pair of loons!"
United States
Melinda M.
The price is CA $255
CA $452 total
includes taxes & fees
Nov 13 - Nov 14
Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
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 Cundys Harbor Hotel Reviews

A lobby with a fireplace, seating area, and a welcome sign.
Hampton Inn Bath (Brunswick Area)

Hampton Inn Bath (Brunswick Area)

Hampton Inn Bath (Brunswick Area)
Bath

10/10 Excellent

Loved the location, everything was clean, and the staff was super helpful!
Canada
Shelley
Reviewed March 1, 2026
Hampton Inn Bath (Brunswick Area)

Find out more about Cundys Harbor

Everything you need to know about Cundys Harbor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cundys Harbor vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cundys Harbor vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cundys Harbor vacation rentals we have selected for you start as low as CA $111 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 vacation 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 vacation.

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 vacation rentals in Cundys Harbor?

Yes, we offer vacation rentals near the most popular attractions in Cundys Harbor, or you can go with a more remote option if you're looking for a relaxing stay.

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

Full sized home: This vacation home near Cundys Harbor offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Cundys Harbor?

Choose from 3 Expedia vacation rentals in Cundys Harbor for a memorable vacation.

What can I see and do in Cundys Harbor?

While exploring the area, visit family-friendly sights like Maine Maritime Museum, or get outside and enjoy nature at Bates-Morse Mountain Conservation Area. In the larger area, you’ll find Bailey Island Bridge and Popham Beach State Park.

What are vacation rentals like in Cundys Harbor?

Vacation rentals are privately owned properties you can reserve for several days or longer in Cundys Harbor. 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 a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family trips.