Cundys Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Cundys Harbor vacation rentals

A deck with white railings overlooking a body of water, boats, and a forested shoreline.

1. 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.
$274 nightly
The price is $276
Nov 15 - Nov 16
Total with taxes and fees
Captains Watch: A Coastal Escape
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
$194 nightly
The price is $205
Nov 8 - Nov 9
Total with taxes and fees
Mid Coast Getaway w/ water views
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

3. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (23 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$278 nightly
The price is $279
Nov 8 - Nov 9
Total with taxes and fees
Fantastic Waterfront Views
A two-story house with a covered porch, a garage, and a front yard with potted plants.

4. 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
$107 nightly
The price is $117
Dec 1 - Dec 2
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
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.

5. 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.
$222 nightly
The price is $236
Nov 8 - Nov 9
Total with taxes and fees
2 bedroom w/ expansive water views
A narrow hallway with a window on the right, leading to a room with a visible door.

6. 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.
$194 nightly
The price is $211
Nov 9 - Nov 10
Total with taxes and fees
Modern style in historic building in downtown Bath
A wooden deck with outdoor seating and string lights.

7. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay!"
United States
Erika T.
$319 nightly
The price is $348
Nov 30 - Dec 1
Total with taxes and fees
Full sized home
A covered porch with a view of a lake and trees.

8. 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.
$357 nightly
The price is $360
Nov 16 - Nov 17
Total with taxes and fees
Mere Point Sunrise Views at Eastern Shore!
A spacious living room with a wooden staircase, a dining area with chairs, and a cozy seating area with a plaid sofa.

9. 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.
$485 nightly
The price is $529
Nov 22 - Nov 23
Total with taxes and fees
Sweet comfy cottage on Small Point Road
A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

10. 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
$155 nightly
The price is $169
Nov 6 - Nov 7
Total with taxes and fees
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

11. 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.
$175 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sunset Hideaway on Bailey Island
A silver convertible car parked in front of a red house with a garden.

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
$173 nightly
The price is $189
Nov 26 - Nov 27
Total with taxes and fees
1BR Apt. Authenticity. Value. Walk to everything, Sundeck. Big yard. Treehouse.
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

13. 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.
$352 nightly
The price is $354
Nov 10 - Nov 11
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
A spacious living room with a large window overlooking a lake, a flat-screen TV mounted on the wall, and a round wooden coffee table.

14. Casco Bay Oceanfront Retreat by Everrow

Casco Bay Oceanfront Retreat by Everrow
Freeport
10.0 out of 10, Exceptional, (13 reviews)
"What can I say about my stay; peaceful, beautiful views, and relaxing! Home was clean with modern finishes but super comfortable for my four guests. The downstairs area is very private from the main floor. The yard was a great space where we had our outdoor fire looking up at the stars at night. The deck was perfect for our family lunch and dinners. We took chairs down to the beach area to sit closer to the water which was perfect. It's super close to town, Wolfe's Neck and other amenities....
United States
Lisa E.
$764 nightly
The price is $833
Nov 8 - Nov 9
Total with taxes and fees
Casco Bay Oceanfront Retreat by Everrow
A modern kitchen with white cabinetry, a central island with stools, a refrigerator, and a microwave.

15. 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.
$340 nightly
The price is $371
Nov 8 - Nov 9
Total with taxes and fees
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

16. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
$357 nightly
The price is $378
Nov 8 - Nov 9
Total with taxes and fees
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A modern kitchen with a dishwasher, a dining area with chairs, and a red refrigerator.

17. 2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very good, (16 reviews)
"Clean convenient location and quiet with comfortable beds. Just what we needed. "
United States
caralyn g.
$243 nightly
The price is $265
Nov 8 - Nov 9
Total with taxes and fees
2King Bed BR Private Apt Downtown Brunswick
A living room with a grey sofa, a coffee table, and a dining area with a wooden table and chairs.

18. Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
8.8 out of 10, Excellent, (28 reviews)
"Perfect spot for us to spend a weekend up at Bowdoin where "
United States
Michaela M.
$366 nightly
The price is $399
Dec 1 - Dec 2
Total with taxes and fees
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

19. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
$1,992 nightly
The price is $2,171
Nov 8 - Nov 9
Total with taxes and fees
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

20. 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.
$296 nightly
The price is $323
Nov 8 - Nov 9
Total with taxes and fees
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
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 spacious living area with a curved staircase, a round glass coffee table, and a seating arrangement.
The Federal

The Federal

The Federal
Brunswick

10/10 Excellent

We booked our stay at The Federal just because it looked nice and seemed like a good price. What we discovered was a wonderful and chic hotel with an extremely comfortable room in a completely remodeled hotel. We’ll definitely stay at The Federal again.
United States
Ryan
Reviewed November 29, 2024
The Federal

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Cundys Harbor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $116 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.