Best Vacation Homes in Pleasant Point
New
House
5 Bedrooms
2 Baths
8 Guests
2500 ft²
Fireplace/Heating
Pet Friendly
Kitchen
Parking
R19,958/Night
7 Nights - R139,699
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
11 Guests
3293.76 ft²
Private Beach
Oceanfront
Skiing- Fireplace/Heating
R5,653/Night
7 Nights - R39,568
Cottage
10.0(30 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
Ocean View
Balcony/Terrace
R4,355/Night
7 Nights - R30,488
House
10.0(1 Review)
1 Bedroom
2 Baths
5 Guests
1280.91 ft²
- Oceanfront
- Ocean View
View- Pet Friendly
R8,388/Night
7 Nights - R58,717
Cottage
10.0(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,314/Night
7 Nights - R37,195
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,625/Night
7 Nights - R25,379
House
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
900 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R9,172/Night
7 Nights - R64,205
Cabin
9.8(80 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R4,324/Night
7 Nights - R30,273
Pleasant Point Luxury Rentals
House
9.8(6 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Internet
R19,199/Night
7 Nights - R134,393
House
3 Bedrooms
2 Baths
8 Guests
2900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R18,896/Night
7 Nights - R132,267
House
4 Bedrooms
2 Baths
7 Guests
2500 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
R17,068/Night
7 Nights - R119,478
House
9.8(59 Reviews)
8 Bedrooms
6 Baths
18 Guests
4000 ft²
- Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
R15,992/Night
7 Nights - R111,947
House
4 Bedrooms
4 Baths
8 Guests
4300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R15,269/Night
7 Nights - R106,888
House
10.0(66 Reviews)
4 Bedrooms
3 Baths
11 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R15,089/Night
7 Nights - R105,619
House
1 Bedroom
5 Baths
8 Guests
4294.8 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R14,832/Night
7 Nights - R103,823
House
1 Bedroom
3 Baths
8 Guests
2895.49 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
R13,184/Night
7 Nights - R92,287
Pleasant Point Pet Friendly Vacation Rentals
Apartment
9.8(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
1150 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R3,966/Night
7 Nights - R27,752
House
5.0(1 Review)
1 Bedroom
1 Bath
3 Guests
581.25 ft²
- Pet Friendly
Child Friendly
Sports/Activities
Security/Safety
R8,143/Night
7 Nights - R57,004
House
9.8(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R4,042/Night
7 Nights - R28,296
House
2.5(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
R4,213/Night
7 Nights - R29,499
Cottage
9.8(31 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,533/Night
7 Nights - R17,732
Apartment
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
R2,874/Night
7 Nights - R20,122
Apartment
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
R2,799/Night
7 Nights - R19,594
Apartment
1 Bedroom
1 Bath
4 Guests
500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R2,485/Night
7 Nights - R17,386
Pleasant Point Large Vacation Homes
House
10.0(95 Reviews)
5 Bedrooms
3 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R11,779/Night
7 Nights - R82,448
House
10.0(21 Reviews)
5 Bedrooms
2 Baths
9 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,235/Night
7 Nights - R36,651
House
9.8(27 Reviews)
8 Bedrooms
3 Baths
14 Guests
3500 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R12,404/Night
7 Nights - R86,832
House
8.6(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R8,173/Night
7 Nights - R57,218
House
7.0(12 Reviews)
8 Bedrooms
2 Baths
20 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,876/Night
7 Nights - R55,141
House
5 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
R12,302/Night
7 Nights - R86,123
House
10.0(58 Reviews)
5 Bedrooms
3 Baths
11 Guests
3000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,742/Night
7 Nights - R54,202
House
10.0(4 Reviews)
5 Bedrooms
3 Baths
11 Guests
3200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R8,240/Night
7 Nights - R57,679
Why Choose Rent By Owner for your Pleasant Point 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 Pleasant Point
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you experience the region’s natural beauty and tranquil atmosphere at its best, making your stay in Pleasant Point, Cushing, Maine, USA, truly memorable.
Peak Season Highlights
Summer (June to August)
During the warmest months, this destination experiences its peak visitation period, making it ideal for enjoying the scenic beauty and outdoor activities that the region offers.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to October)
The vibrant autumn foliage attracts visitors seeking picturesque views, providing a perfect backdrop for outdoor excursions and leisure stays.
Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Spring (April to May)
As the area awakens from winter, fewer travelers arrive, offering a quieter experience ideal for those seeking tranquility and early-season scenery.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Winter (November to March)
This off-peak time sees limited visitors, but if you enjoy winter landscapes and cozy stays, it provides a peaceful retreat away from crowds.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Weekly Weather Forecast for Pleasant Point
How to Book Your Pleasant Point 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 Pleasant Point
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 outdoor dining with picnic tables and BBQ grills, perfect for hosting gatherings amid the scenic surroundings of the area.
- Relax on spacious decks or patios that offer picturesque views of the region’s natural beauty.
- Take advantage of private waterfront access, such as docks or shoreline setups, ideal for boating or fishing activities.
- Benefit from well-maintained gardens or landscaped yards that enhance your outdoor experience in this destination.
- Utilize fire pits or outdoor fireplaces for cozy evenings under the stars, capturing the charm of the region's evening air.
- Make use of designated outdoor recreation areas like swimming pools or sports courts available nearby or within the property.
- Experience the serenity with nature trails or hiking paths that allow you to immerse yourself in the natural environment of the area.
Top Attractions Around Pleasant Point
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic trails that showcase the natural beauty surrounding Pleasant Point in Cushing, Maine.
Family Activities
- Explore the Cushing Historical Society Museum: Discover fascinating local history that offers an engaging indoor activity perfect for families visiting this charming destination.
- Enjoy outdoor adventures at the nearby Cushing Community Park: Relax and play in the scenic park, which provides open spaces and recreational facilities suitable for all ages.
- Take a boat tour of the region's waterways: Experience the natural beauty of the area's coastal and inland waterways on guided boat tours designed for family fun and learning.
- Visit the local Farmer’s Market: Taste fresh, regional produce and artisanal goods while supporting local vendors during your stay in this peaceful destination.
Adult Activities
- Explore the Cushing Historical Society Museum: Gain insights into the area's rich heritage and maritime history through engaging exhibits and local artifacts.
- Enjoy boating and kayaking on the serene waters: Experience the tranquility of this scenic region by paddleboarding or renting a boat to explore the nearby waterways.
- Visit local art galleries and craft shops: Immerse yourself in the region's creative scene by browsing unique artworks and handcrafted items in charming local venues.
- Attend seasonal festivals and community events: Participate in lively gatherings that celebrate local traditions, music, and cuisine during your stay here.
Pleasant Point Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the region’s scenic outdoor spaces to enjoy activities like hiking, fishing, or simply relaxing amidst the natural beauty here.
- Plan for Seasonal Activities: Align your visit with local seasonal events or outdoor pursuits to experience the area's vibrant community spirit and unique traditions.
- Utilize Nearby Resources: Make the most of the local visitor centers or information spots to discover hidden gems and practical tips during your stay in this destination.
- Choose the Right Accommodation: Select a vacation rental that offers easy access to key attractions and provides comforts tailored to your travel needs in this part of Maine.
Transportation Options
- Local Taxi Services: Conveniently explore the area with reputable taxi companies that provide reliable transportation from your vacation rental here to local attractions and nearby towns.
- Public Transit Options: Buses serve the region, offering an affordable way to travel around Cushing and connect to other parts of Maine without the need for a car.
- Car Rentals: Renting a vehicle gives you the flexibility to discover the scenic surroundings of this destination at your own pace, with several agencies available nearby.
- Private Shuttle Services: For comfort and convenience, private shuttles operate between popular destinations in the region, making day trips and airport transfers seamless during your stay.
Local Customs Options
- Respect for Waterways: Locals in the area often honor their connection to the region’s waterways by practicing responsible boating and fishing customs.
- Community Gatherings: Participating in local events and gatherings is a valued tradition that helps visitors connect with residents and embrace the regional culture.
- Preservation of Nature: There is a strong emphasis on environmental stewardship, encouraging visitors to keep the natural beauty of this destination pristine.
- Historical Appreciation: Respecting the area's history by observing local landmarks and respecting private properties is part of the community’s ethos.
Frequently Asked Questions About Pleasant Point?
1. What are the top vacation rentals in Pleasant Point?
There are a lot of options in Pleasant Point. If you plan on staying in the Pleasant Point area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pleasant Point:
- Historic "Wilbur Morse" Friendship Maine Ocean Home
- Luxurious ocean-front home with dock
- Honeymoon Cottage (pet-friendly)
- Friendship Harbor Waterfront Home
- Unique ISLAND Living off the grid -Waterfront cottage
- Midcoast Waterfront Maine Home
- Dockside Retreat!
- House and bunkhouse. Includes kayaks and SUPs
- Private, light filled property with private water access
- Cozy waterfront cottage overlooking Muscongus Bay with stunning sunset views.
2. Which vacation homes in Pleasant Point are best for families?
If you are looking for a family-friendly vacation home in Pleasant Point, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pleasant Point:
3. How many Rentbyowner vacation rentals are available in Pleasant Point?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 98 in the Pleasant Point 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 Pleasant Point.
4. What is the cancellation policy for vacation rentals in Pleasant Point, Cushing, Maine?
The cancellation policy varies depending on the individual property listing. You should review the specific cancellation terms provided in the listing details or contact the property owner directly to understand the applicable refund and cancellation conditions.
5. How can I ensure my booking in this region is secure and reliable?
To guarantee a safe and dependable booking experience, always verify the host’s reviews and ratings, read the detailed listing information carefully, and communicate directly with the property owner if you have any questions before confirming your reservation.
6. Are there any additional fees associated with the vacation rental in the area?
Additional fees such as cleaning, service charges, or security deposits are typically listed in the property details or during the booking process. It’s recommended to check these specifics beforehand to avoid surprises upon arrival.
7. What amenities are usually included in vacation rentals here?
Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking. For specific features such as outdoor spaces or special equipment, review the property description thoroughly or reach out to the owner for confirmation.
8. How do I change or update my reservation in this destination?
To modify your booking, contact the property owner or the customer support team through the booking platform used. Be sure to review the property's policies on changes or cancellations prior to making adjustments.
Pleasant Point Top Rated Vacation Rentals
House
10.0(17 Reviews)
3 Bedrooms
1 Bath
6 Guests
Spa- Fireplace/Heating
Pool- Ocean View
R2,521/Night
7 Nights - R17,650
House
10.0(7 Reviews)
4 Bedrooms
3 Baths
9 Guests
1550 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
R6,180/Night
7 Nights - R43,259
