Best Vacation Homes in Cumberland
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Cumberland Luxury Rentals
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Cumberland Pet Friendly Vacation Rentals
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Cumberland Large Vacation Homes
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Why Choose Rent By Owner for your Cumberland 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 Cumberland
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you can fully enjoy the tranquil beauty and welcoming atmosphere of this destination, making your stay in Cumberland more memorable and relaxing.
Peak Season Highlights
Summer (June to August)
During the warm summer months, this destination experiences its peak season as visitors flock here to enjoy the pleasant weather and outdoor activities. It’s an ideal time to book vacation rentals for a comfortable and lively stay.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Autumn (September to October)
The early fall months bring colorful foliage and crisp air, making it another popular period for visiting the area. Booking your vacation rentals in this season ensures you experience the scenic beauty and mild weather.
Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F
Off-Season Highlights
Winter (December to February)
Cold winter weather leads to a quieter period here, with fewer visitors. It’s a good time to find more affordable vacation rentals and enjoy peaceful surroundings away from the bustling crowds.
Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F
Spring (March to May)
As the region transitions from winter, the early spring months see less tourist activity. This is an excellent opportunity to secure vacation rentals for a tranquil escape before the busy summer season begins.
Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Cumberland
How to Book Your Cumberland 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 Cumberland
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 a private patio or deck overlooking scenic landscapes.
- Take advantage of spacious yards ideal for outdoor games and relaxing in the fresh air.
- Make use of a barbecue grill to host memorable cookouts during your stay.
- Benefit from access to nearby hiking trails or nature walks in the region.
- Relax by a fire pit in the evenings, perfect for gathering with family and friends.
- Utilize outdoor seating areas designed for soaking up the tranquility of the area's natural beauty.
- Explore nearby water features such as lakes or ponds suitable for kayaking or canoeing.
Top Attractions Around Cumberland
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities such as hiking, biking, and exploring scenic nature trails just minutes from your vacation rental in Cumberland.
Family Activities
- Pineland Farms Trail System: Explore this extensive trail network for family-friendly hiking and biking, offering scenic views and outdoor fun in the area.
- Deering Oak Park: Enjoy a relaxing day at this charming park with playgrounds, picnic areas, and open spaces perfect for family gatherings in Cumberland Center.
- Cumberland Fairgrounds: Attend seasonal events and local fairs that provide entertainment and activities suitable for all ages here in this welcoming region.
- Seaside Explorations: Experience the natural beauty of nearby coastal spots, ideal for picnicking, beachcombing, and discovering Maine’s maritime charm with your family.
Adult Activities
- Explore the Cumberland Farmers' Market: Here, you can enjoy a vibrant local scene and sample fresh, regional produce that captures the essence of the area's agricultural charm.
- Visit the Highland Green Golf Course: Perfect for golf enthusiasts, this scenic course provides a relaxing way to enjoy the natural beauty and well-maintained greens of the region.
- Discover the Harraseeket Historical Society: Delve into local history through engaging exhibits and programs that highlight the rich heritage of the community nearby.
- Attend a performance at the Maine State Music Theatre: Experience live entertainment at this renowned venue, showcasing talented performers in productions that reflect the region's cultural vibrancy.
Other Places to Stay in Cumberland, ME
Cumberland Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Amenities: Take advantage of nearby shops, restaurants, and outdoor spaces to enhance your stay in this charming area.
- Plan Outdoor Activities: Utilize the region’s natural beauty by scheduling visits to parks, trails, or water activities right outside your vacation rental.
- Connect with the Community: Engage with local events or farmers’ markets to get a true taste of the area's culture and hospitality.
- Optimize Your Booking: Choose a well-located property that offers easy access to key attractions and conveniences here for a more enjoyable visit.
Transportation Options
- Local Bus Services: You can rely on the region's local bus network for convenient transportation around Cumberland and its nearby areas, making it easy to explore the destination without a car.
- Taxi and Rideshare Options: Taxis and rideshare services provide flexible, on-demand transportation to connect you with key points of interest within this part of Maine.
- Car Rentals: Renting a vehicle offers the freedom to discover the area at your own pace, especially useful for visiting attractions outside the immediate vicinity.
- Airport Transfers: The nearby airports offer shuttle services and private transfers that can conveniently transport you directly to your vacation rental in Cumberland or the surrounding region.
Local Customs Options
- Lobster Boil Traditions: Participating in a local lobster boil reflects the region's rich maritime heritage and your opportunity to enjoy authentic Maine seafood.
- Seasonal Celebrations: Engaging in seasonal festivals and community events allows you to experience the area's vibrant local culture firsthand.
- Respect for Nature: Practicing environmentally conscious behaviors, such as conservation efforts and respectful outdoor recreation, aligns with the community’s commitment to preserving its natural beauty.
- Historical Appreciation: Appreciating the region’s history through visits to local landmarks and listening to stories shared by residents offers deeper insight into this destination’s unique roots.
Frequently Asked Questions About Cumberland?
1. What are the top vacation rentals in Cumberland?
There are a lot of options in Cumberland. If you plan on staying in the Cumberland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cumberland:
- Fully Furnished Executive/Garden Apartment In Falmouth, Maine
- Ocean View Cottage Falmouth Foreside
- A Waterfront Retreat with Private Deep Water Dock. Dogs allowed upon request
- Simonson Lakeside 4 Bedrooms
- Executive Falmouth Waterfront Home on the Presumpscot River
- Rustic Charm close to Portland
- Simonson Lakeside on Highland Lake
- Private Lakefront Home-Hot Tub-Great for Families-Large Yard-Quiet-Shallow Entry
- Midcentury Modern 2 Bedroom Village Oasis
- Waterfront home on Forest Lake in Gray, Maine. Perfect for 1 or 2 couples.
2. How many vacation rentals have private pools in Cumberland?
There are 2 vacation rentals with private pools near Cumberland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Cumberland are best for families?
If you are looking for a family-friendly vacation home in Cumberland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cumberland:
4. How many Rentbyowner vacation rentals are available in Cumberland?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 142 in the Cumberland 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 Cumberland.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the specific property listing. You should review the property's cancellation terms carefully before booking or contact the owner directly for detailed information.
6. Are there any additional fees associated with my reservation in Cumberland Center?
Additional fees such as cleaning, service charges, or security deposits are typically outlined in the listing details. It's recommended to read the full description or reach out to the property owner for clarification.
7. How do I find the most suitable vacation rental for my stay in Maine?
To find the ideal property, use the search filters and read reviews thoroughly. Each listing provides details about amenities and location, so reviewing these can help you select the best option for your visit.
8. Can I modify or extend my stay at a vacation rental in Cumberland?
Modifications or extensions depend on the property's availability and the owner's policies. Contact the host directly through the platform to inquire about making changes to your reservation.
9. What amenities are typically included in vacation rentals here?
Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and parking. Specific features are listed on each property page, so reviewing these details ensures your needs are met before booking.
Cumberland Top Rated Vacation Rentals
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