Best Vacation Homes in Cumberland County
Apartment
10.0(56 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $148/Night
7 Nights - US $1,038
Bed & Breakfast
10.0(8 Reviews)
7 Bedrooms
6 Baths
17 Guests
274.48 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
US $231/Night
7 Nights - US $1,616
Bed & Breakfast
10.0(183 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $331/Night
7 Nights - US $2,318
Apartment
9.2(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $846/Night
7 Nights - US $5,920
House
10.0(3 Reviews)
5 Bedrooms
2 Baths
10 Guests
2195.84 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
US $1,280/Night
7 Nights - US $8,960
House
7 Bedrooms
4 Baths
16 Guests
Oceanfront
Hot Tub
Skiing- Fireplace/Heating
US $2,500/Night
7 Nights - US $17,497
Cottage
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $1,508/Night
7 Nights - US $10,557
New
House
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,308/Night
7 Nights - US $9,156
Cumberland County Luxury Rentals
House
18 Bedrooms
8 Baths
50 Guests
10000 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $6,325/Night
7 Nights - US $44,275
House
9.6(7 Reviews)
5 Bedrooms
8 Baths
10 Guests
10000 ft²
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
US $5,476/Night
7 Nights - US $38,332
House
10.0(11 Reviews)
6 Bedrooms
6 Baths
15 Guests
13307 ft²
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $4,727/Night
7 Nights - US $33,092
House
10.0(18 Reviews)
8 Bedrooms
4 Baths
27 Guests
5600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $3,904/Night
7 Nights - US $27,331
House
10.0(2 Reviews)
10 Bedrooms
4 Baths
18 Guests
4793 ft²
- Oceanfront
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $3,858/Night
7 Nights - US $27,006
House
10.0(6 Reviews)
12 Bedrooms
5 Baths
30 Guests
5700 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- View
US $3,698/Night
7 Nights - US $25,885
House
10.0(34 Reviews)
16 Bedrooms
9 Baths
35 Guests
10000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $3,633/Night
7 Nights - US $25,434
House
5 Bedrooms
5 Baths
14 Guests
3993.41 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $3,585/Night
7 Nights - US $25,093
Cumberland County Pet Friendly Vacation Rentals
New
House
5 Bedrooms
3 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $743/Night
7 Nights - US $5,203
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
12 Guests
1808.34 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $1,087/Night
7 Nights - US $7,609
Villa
1 Bedroom
1 Bath
Pool- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,253/Night
7 Nights - US $15,768
New
Cottage
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $717/Night
7 Nights - US $5,018
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1786.81 ft²
- Fireplace/Heating
- View
Breakfast- Pet Friendly
US $417/Night
7 Nights - US $2,919
House
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $703/Night
7 Nights - US $4,921
New
Cottage
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $536/Night
7 Nights - US $3,755
New
House
1 Bedroom
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $489/Night
7 Nights - US $3,424
Cumberland County Large Vacation Homes
Apartment
9.6(10 Reviews)
1 Bedroom
1 Bath
12 Guests
1 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,672/Night
7 Nights - US $11,707
Villa
10.0(1 Review)
5 Bedrooms
4 Baths
12 Guests
4004.17 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $2,942/Night
7 Nights - US $20,591
Villa
1 Bedroom
1 Bath
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $1,659/Night
7 Nights - US $11,611
Apartment
7.8(28 Reviews)
2 Bedrooms
1 Bath
10 Guests
1000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $567/Night
7 Nights - US $3,968
House
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Skiing
- Fireplace/Heating
- Breakfast
- Parking
US $437/Night
7 Nights - US $3,059
House
7.8(12 Reviews)
2 Bedrooms
2 Baths
10 Guests
1064 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $426/Night
7 Nights - US $2,982
Cabin
2 Bedrooms
1 Bath
12 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $1,699/Night
7 Nights - US $11,890
New
House
1 Bedroom
4 Baths
12 Guests
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $487/Night
7 Nights - US $3,409
Why Choose Rent By Owner for your Cumberland County 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 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
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
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
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
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
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.
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.
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
Portland
Bridgton
Highland Lake
Great Island
Scarborough
Sebago
Downtown Portland
Freeport
Harpswell
Naples
Standish
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.
Cumberland County Vacation Rental Frequently Asked Questions
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:
- Romantic getaway for 2nnBeautiful time of year !nn2 day's open Augnnnnnnnnnnnn
- Penthouse Two Master Waterfront Suite with Rooftop
- Private w/waterfront <5 min to Pleasant Mt & town. Dock, pool table, ping-pong
- Old Port Penthouse Suite - Amazing Harbor Views
- Downtown Penthouse Suite - Stunning Harbor Views
- Waterfront Two Master Suite Penthouse with Rooftop
- The James Place Inn B&B
- Fully Furnished Executive/Garden Apartment In Falmouth, Maine
- Maine Oceanfront Home
- 5 Star Back Cove Apartment with water view!
2. How many vacation rentals have private pools in Cumberland County?
There are 51 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 3236 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
House
10.0(64 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $382/Night
7 Nights - US $2,671
House
10.0(57 Reviews)
3 Bedrooms
1 Bath
9 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $268/Night
7 Nights - US $1,875
Apartment
10.0(48 Reviews)
1 Bedroom
1 Bath
3 Guests
700 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $284/Night
7 Nights - US $1,988
House
10.0(43 Reviews)
5 Bedrooms
1 Bath
10 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $865/Night
7 Nights - US $6,055
House
10.0(43 Reviews)
3 Bedrooms
2 Baths
10 Guests
1490 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $309/Night
7 Nights - US $2,162
Other
10.0(33 Reviews)
3 Bedrooms
2 Baths
6 Guests
2400 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $342/Night
7 Nights - US $2,396
House
10.0(29 Reviews)
4 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $447/Night
7 Nights - US $3,128
House
10.0(29 Reviews)
4 Bedrooms
2 Baths
8 Guests
1512 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $400/Night
7 Nights - US $2,798
