Discover Your Perfect Cumberland County Vacation Homes

Best Vacation Homes in Cumberland County

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10.0 (182 Reviews)
Bed & Breakfast
The James Place Inn B&B
  • Air Conditioner
  • TV
  • Balcony/Terrace
View Availability
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Why Choose Rent By Owner for your Cumberland County Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Cumberland County

When should you plan your Vacation Rentals stay?

Choosing the best time to vacation in this destination can enhance your experience, allowing you to enjoy the region's natural beauty and local charm at its most vibrant and serene.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for outdoor activities in this region.

Average Temperature Daytime: around 75-85°F - Nighttime: 55-65°F
autumn
Fall (September to November)

The fall season offers vibrant foliage and mild temperatures, perfect for exploring the area's scenic landscapes and charming towns.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

Winter experiences cooler temperatures and quieter surroundings, providing a peaceful retreat for those seeking winter recreation or cozy getaways.

Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F
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Spring (March to May)

Spring brings milder weather and budding natural beauty, offering a less crowded time to explore the area's attractions and scenic beauty.

Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F

Weekly Weather Forecast for Cumberland County

How to Book Your Cumberland County 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 County

More Top-Rated Vacation Rentals in Cumberland County Area

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 areas perfect for gatherings and meals amidst scenic surroundings.
  • Take advantage of private or shared patios and decks to relax and unwind outdoors.
  • Make the most of spacious yards or gardens for outdoor activities or simply soaking up the sunshine.
  • Experience the convenience of on-site parking facilities, making your arrival and exploration easy.
  • If available, utilize nearby nature trails or walking paths to explore the area's natural beauty.
  • Benefit from access to outdoor fire pits or grills to enjoy cozy evenings with family and friends.
  • Some properties feature outdoor pools or hot tubs, providing a luxurious way to relax after a day of exploring the region.

Top Attractions Around Cumberland County

What attractions are nearby?

In this region, you can enjoy a variety of outdoor activities such as exploring scenic parks, hiking along picturesque trails, or relaxing by the waterfront, all within easy reach of your chosen vacation rentals.

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Family Activities

  • Exploring the Portland Head Light: You can enjoy family-friendly walks along the scenic coastline while visiting this iconic lighthouse in the region.
  • Visiting Portland Museum of Art: Engaging exhibits and interactive programs here make it an excellent educational outing for families seeking cultural experiences in the area.
  • Relaxing at Mackworth Island: This island offers lush trails, a sandy beach, and panoramic views, providing a perfect spot for outdoor family adventures.
  • Discovering Sebago Lake: Spend your days boating, fishing, or picnicking around this popular destination known for its natural beauty and family-oriented activities nearby.
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Adult Activities

  • Whale Watching Tours: Embark on a guided whale watching tour to witness the majestic marine life that frequents these waters, offering an unforgettable experience close to your Cumberland County accommodation.
  • Coastal Hiking Trails: Explore scenic coastal hiking trails in the area, where you can enjoy stunning views of the Atlantic Ocean and the region’s natural beauty right from your rental base.
  • Local Seafood Dining: Savor fresh, locally caught seafood at renowned restaurants nearby, providing a taste of the region’s culinary heritage just moments from your stay.
  • Boat Rentals and Water Activities: Take advantage of boat rentals and water activities like kayaking or paddleboarding, allowing you to explore the pristine waters surrounding this popular vacation destination.

Other Places to Stay in Cumberland County, ME

New England
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Portland
Portland Vacation Rentals
Bridgton
Bridgton Vacation Rentals
Highland Lake
Highland Lake Vacation Rentals
Scarborough
Scarborough Vacation Rentals
Great Island
Great Island Vacation Rentals
Sebago
Sebago Vacation Rentals
Downtown Portland
Downtown Portland Vacation Rentals
Freeport
Freeport Vacation Rentals
Naples
Naples Vacation Rentals
Harpswell
Harpswell Vacation Rentals
South Portland
South Portland Vacation Rentals
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Cumberland County Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the area's scenic parks and trails to enjoy hiking, biking, or picnicking during your stay in this charming destination.
  • Visit nearby coastal spots: Make time to relax on the region’s beaches or explore waterfront areas that highlight the natural beauty of the surroundings.
  • Plan for seasonal events: Check out the local event calendar to immerse yourself in seasonal festivities and community gatherings that showcase the area's culture.
  • Choose well-located vacation rentals: Select properties close to key attractions and amenities to maximize your time and convenience here in the region.

Transportation Options

  • Portland International Jetport: You can easily access the region by flying into this nearby airport, offering convenient domestic and limited international flights.
  • Amtrak Downeaster: Traveling along the coast is simple with this train service, connecting here to major cities like Boston and Portland for a scenic and relaxing journey.
  • Local Bus Services: The area's public transit options provide affordable and reliable transportation within Cumberland County and surrounding towns.
  • Car Rentals and Taxis: Renting a car or booking a taxi allows you to explore local sights at your own pace, especially useful for reaching picturesque coastal destinations and outdoor attractions.

Local Customs Options

  • Seafood Dining Etiquette: Locals in this region take pride in their seafood and often gather for communal meals, so embracing the local dining customs can enhance your experience here.
  • Seasonal Festivities: Participating in seasonal celebrations, such as summer festivals or fall harvest events, is a cherished tradition that reflects the area's rich cultural heritage.
  • Respect for Natural Resources: Visitors are encouraged to follow sustainable practices when exploring the region's parks and coastal areas to preserve the natural beauty for future generations.
  • Historical Appreciation: Acknowledging the area's history through respectful behavior at local museums and historic landmarks will enrich your understanding of this destination's unique background.

Frequently Asked Questions About Cumberland County?

1. What are the top vacation rentals in Cumberland County?

There are a lot of options in Cumberland County. If you plan on staying in the Cumberland County 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 County:

2. How many vacation rentals have private pools in Cumberland County?

There are 48 vacation rentals with private pools near Cumberland County. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cumberland County are best for families?

If you are looking for a family-friendly vacation home in Cumberland County, 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 County:

4. How many Rentbyowner vacation rentals are available in Cumberland County?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 3070 in the Cumberland County 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 County. 

5. What is the cancellation policy for vacation rentals in Cumberland County, Maine?

Cancellation policies vary depending on the property owner. You should review the specific listing details or contact the host directly to understand the cancellation terms applicable to your reservation.

6. Are there any additional fees I should be aware of when booking a vacation rental in the area?

Additional fees such as cleaning fees, service charges, or occupancy taxes are often included in the listing details. It’s recommended to read the full description or reach out to the owner for clarification before confirming your reservation.

7. How do I find a vacation rental that suits my needs in Cumberland County, Maine?

You can filter your search based on property type, amenities, and price range to find a rental that fits your preferences. For personalized assistance, contacting the property owner or support team may help ensure your chosen accommodation aligns with your travel plans.

8. What should I know about check-in and check-out times for rentals in this region?

Check-in and check-out times are specified in each listing. Since policies can differ, it’s best to confirm these details with the property owner to coordinate your arrival and departure smoothly.

9. Is there a flexible booking option if my travel plans change unexpectedly?

Flexible booking options depend on the individual property's policies. To avoid potential issues, review the specific cancellation and modification terms listed or discuss your situation directly with the owner prior to booking.

Cumberland County Top Rated Vacation Rentals

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