Best Vacation Homes in Cundys Harbor
New
House
8.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1593 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $433/Night
7 Nights - US $3,031
House
8.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
721.18 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Child Friendly
US $365/Night
7 Nights - US $2,555
Hotel
8.4(358 Reviews)
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
- Pet Friendly
US $232/Night
7 Nights - US $1,626
New
House
2 Bedrooms
1 Bath
6 Guests
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $259/Night
7 Nights - US $1,813
New
House
7.8(5 Reviews)
1 Bedroom
2 Baths
4 Guests
1732.99 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
View
US $382/Night
7 Nights - US $2,671
Cottage
10.0(13 Reviews)
1 Bedroom
1 Bath
2 Guests
578 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $339/Night
7 Nights - US $2,375
House
10.0(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $452/Night
7 Nights - US $3,166
Cabin
10.0(5 Reviews)
2 Bedrooms
1 Bath
3 Guests
510 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $205/Night
7 Nights - US $1,435
Cundys Harbor Luxury Rentals
House
10.0(6 Reviews)
6 Bedrooms
3 Baths
16 Guests
5600 ft²
Private Pool- Oceanfront
Hot Tub- Fireplace/Heating
US $2,944/Night
7 Nights - US $20,608
House
10.0(52 Reviews)
6 Bedrooms
3 Baths
16 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,799/Night
7 Nights - US $12,590
House
9.8(43 Reviews)
5 Bedrooms
4 Baths
8 Guests
4500 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,744/Night
7 Nights - US $12,208
House
10.0(20 Reviews)
5 Bedrooms
4 Baths
14 Guests
9000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,635/Night
7 Nights - US $11,445
House
10.0(25 Reviews)
5 Bedrooms
4 Baths
10 Guests
4104 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,345/Night
7 Nights - US $9,415
House
6 Bedrooms
4 Baths
14 Guests
3197 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,178/Night
7 Nights - US $8,248
House
9.8(9 Reviews)
6 Bedrooms
3 Baths
8 Guests
3827 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,068/Night
7 Nights - US $7,477
Cottage
10.0(17 Reviews)
3 Bedrooms
3 Baths
8 Guests
3500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,036/Night
7 Nights - US $7,249
Cundys Harbor Pet Friendly Vacation Rentals
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
937 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $179/Night
7 Nights - US $1,254
Hotel
7.2(127 Reviews)
14 Baths
249.87 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $250/Night
7 Nights - US $1,749
Apartment
9.8(63 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $331/Night
7 Nights - US $2,318
Apartment
9.8(60 Reviews)
1 Bedroom
1 Bath
2 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $319/Night
7 Nights - US $2,236
Cottage
9.8(57 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $406/Night
7 Nights - US $2,842
House
9.8(17 Reviews)
2 Bedrooms
2 Baths
6 Guests
1734 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $477/Night
7 Nights - US $3,342
Cabin
9.8(7 Reviews)
1 Bedroom
1 Bath
2 Guests
780 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $251/Night
7 Nights - US $1,760
House
9.6(59 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $476/Night
7 Nights - US $3,334
Cundys Harbor Large Vacation Homes
Cottage
10.0(1 Review)
7 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,034/Night
7 Nights - US $7,241
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $724/Night
7 Nights - US $5,069
House
9.6(16 Reviews)
5 Bedrooms
3 Baths
14 Guests
2893 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $498/Night
7 Nights - US $3,487
New
House
6 Bedrooms
4 Baths
10 Guests
4041 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,033/Night
7 Nights - US $7,229
House
5 Bedrooms
4 Baths
10 Guests
4600 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $849/Night
7 Nights - US $5,944
House
5 Bedrooms
4 Baths
8 Guests
2388 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $705/Night
7 Nights - US $4,937
House
5 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
Air Conditioner
Internet- Child Friendly
US $966/Night
7 Nights - US $6,765
Why Choose Rent By Owner for your Cundys Harbor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Cundys Harbor
When should you plan your Vacation Rentals stay?
Choosing the right time to visit ensures you make the most of your stay here, whether you're seeking peaceful seclusion or vibrant local activities in this charming region of Maine.
Peak Season Highlights
Summer (June to August)
During the peak summer months, the region experiences warm weather and longer daylight hours, perfect for enjoying outdoor activities and local events.
Average Temperature Daytime: 75-85°F - Nighttime: 60-65°F
Fall (September to October)
Early fall offers mild temperatures and vibrant foliage, making it an ideal time to explore the area’s scenic beauty with fewer crowds.
Average Temperature Daytime: 65-70°F - Nighttime: 50-55°F
Off-Season Highlights
Late Fall to Early Winter (November to December)
As the region transitions into winter, you can enjoy quieter surroundings and the peaceful ambiance of this destination before the holiday season peaks.
Average Temperature Daytime: 45-55°F - Nighttime: 35-40°F
Winter (January to February)
During the coldest months, expect fewer visitors and a serene atmosphere, ideal for those seeking solitude and off-season tranquility.
Average Temperature Daytime: 30-40°F - Nighttime: 20-25°F
Weekly Weather Forecast for Cundys Harbor
How to Book Your Cundys Harbor Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cundys Harbor
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck perfect for relaxing and dining al fresco.
- Take advantage of spacious yards ideal for outdoor games and family activities.
- Benefit from access to a boat dock or mooring, suitable for exploring nearby waters.
- Make use of a well-equipped grill station for outdoor barbecues amidst scenic surroundings.
- Relax in porch or veranda areas that provide stunning views of the region’s natural beauty.
- Utilize outdoor showers or rinsing stations for easy cleanup after seaside adventures.
- Appreciate nearby walking trails or nature paths that showcase the area's coastal charm.
Top Attractions Around Cundys Harbor
What attractions are nearby?
In this charming area, you can enjoy a variety of activities such as exploring scenic coastal walks, kayaking along tranquil waters, and discovering local maritime attractions that highlight the region's rich nautical heritage.
Family Activities
- Harpswell Heritage Land Trust Trails: Explore scenic hiking trails that wind through protected lands, offering families a chance to enjoy the region's natural beauty and wildlife.
- Cundy's Harbor Museum & Maritime History: Discover local maritime history with engaging exhibits and family-friendly activities that highlight the area's rich nautical heritage.
- Harpswell Coastal Kayaking Tours: Experience the calm waters of the harbor on guided kayaking excursions suitable for all ages, providing a fun way to see the coastline from a new perspective.
- Wildlife Watching at Middle Bay Preserve: Spend time observing seabirds and marine life at this tranquil preserve, perfect for family picnics and nature exploration in the region.
Adult Activities
- Sea Kayaking and Paddleboarding: Explore the tranquil waters of this coastal region by renting equipment locally to enjoy a peaceful paddle along scenic coves and shoreline views.
- Fishing Excursions: Join guided fishing trips in the area's renowned waters, offering a relaxing experience that highlights the region's rich marine life.
- Harpswell Historical Society Tour: Discover local history through curated tours that provide insight into the area's maritime heritage and cultural landmarks.
- Sunset Cruises: Embark on an evening cruise to witness breathtaking sunsets over the harbor, creating memorable moments in this charming seaside destination.
Cundys Harbor Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Seafood Markets: Take advantage of the region's fresh seafood offerings to enjoy authentic Maine flavors during your stay.
- Plan Waterfront Activities: Make the most of the area's scenic coastline by engaging in kayaking, boating, or relaxing by the waterfront.
- Visit Nearby Natural Attractions: Discover the area's natural beauty by exploring local parks and scenic spots that showcase Maine's coastal landscape.
- Experience Local Culture and Events: Attend community gatherings or seasonal events to immerse yourself in the area's vibrant local culture.
Transportation Options
- Car Rentals: Renting a car offers you the flexibility to explore the scenic coast and hidden gems around this coastal area at your own pace.
- Local Taxis and Rideshare Services: Convenient for quick trips or when you're looking to avoid parking, these services provide reliable transportation within this region.
- Bicycle Rentals: Biking is an enjoyable way to experience the picturesque surroundings and access quieter spots near your vacation rentals here.
- Public Transportation: Bus services operate in the area, offering an affordable and eco-friendly way to navigate this peaceful coastal destination.
Local Customs Options
- Respect for the Sea:** Locals here have a deep-rooted tradition of respecting maritime practices, which is evident in their careful navigation and preservation of the coastal environment.
- Community Gatherings:** Participating in or observing local events such as seasonal festivals reflects the community-centered spirit that is cherished in this region.
- Preservation of History:** The area's historical customs, including maritime craftsmanship and storytelling, remain integral to daily life and cultural identity.
- Local Seafood Etiquette:** Enjoying fresh catches often involves specific dining manners that honor the region's fishing heritage and sustainability efforts.
Cundys Harbor Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Cundys Harbor?
There are a lot of options in Cundys Harbor. If you plan on staying in the Cundys Harbor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cundys Harbor:
- On Top of the Sea North Harpswell House
- On Sebasco Estates, 4 Bedroom House, Ocean Views, Close to Beaches and Golfing.
- New Listing - Island View Cottage
- 'Camp Card Cove' the Way Life Should Be
- Spacious Waterfront Summer Home with Swimming, Kayaking, and Sunsets
- 700' OCEANFRONT RETREAT, FIRE PIT, 10 ACRES, 6 BR, 8 KAYAKS, 2 PDL BRDS,
- Sunrise Catcher with a Panoramic View!
- Spectacular Waterfront Retreat Close To Portland!
- Classic Maine cottage set on its own peninsula with stunning views
- Amazing Oceanfront Private Cottage Deep H2O Dock
2. Which vacation homes in Cundys Harbor are best for families?
If you are looking for a family-friendly vacation home in Cundys Harbor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cundys Harbor:
3. How many Rentbyowner vacation rentals are available in Cundys Harbor?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 109 in the Cundys Harbor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cundys Harbor.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property. You should review the specific listing details or contact the owner directly to understand their policy regarding cancellations and potential refunds.
5. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are usually specified in the listing. Make sure to read the property details carefully or reach out to the host for clarification before booking.
6. How do I ensure my reservation is secure and confirmed?
Bookings are secured through the platform's trusted payment system once you complete the reservation process. Confirm your reservation details with the property owner if necessary, and keep all correspondence for your records.
7. What amenities can I expect at vacation rentals in this region?
Amenities vary by property, but typical features include full kitchens, outdoor spaces, Wi-Fi, and parking. Check each listing for specific amenities to find the best fit for your stay.
8. Is there a minimum stay requirement for booking a vacation rental here?
Minimum stay requirements depend on the individual property. Review the listing details or contact the host directly to confirm any minimum night restrictions before making your reservation.
Cundys Harbor Top Rated Vacation Rentals
House
10.0(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $416/Night
7 Nights - US $2,910
New
House
2 Bedrooms
3 Baths
6 Guests
1821 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $508/Night
7 Nights - US $3,557
House
9.4(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Oceanfront
Spa- Fireplace/Heating
- Pool
US $438/Night
7 Nights - US $3,068
