Cumberland holiday homes

We found 980 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Cumberland to find one that's perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a pool. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Cumberland

Showing deals for:11 Dec - 18 Dec

Quiet, tree-lined Deering neighborhood setting
Bright and comfortable living room in a quiet Portland neighborhood
Room
Fully equipped kitchen with everything needed for cooking
Exceptional
(50 reviews)

Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland

Portland

8% off
NZ$4,023
for 7 nights, 1 home
NZ$575 per night
includes taxes & fees
Quiet 2BR/2BA Home w/ Parking • Dog-Friendly • Near Downtown Portland
Exterior
Living area
Interior
Private kitchen
Exceptional
(21 reviews)

Entire House - three suites - conferences, reunions, retreats

Westbrook

8% off
NZ$12,891
for 7 nights, 1 home
NZ$1,842 per night
includes taxes & fees
Entire House - three suites - conferences, reunions, retreats
Dining
Living area
Room
Property grounds
Exceptional
(11 reviews)

Luxury Lakefront home on Sebago Lake W/ Sandy Beach

Raymond

8% off
NZ$9,471
for 7 nights, 1 home
NZ$1,353 per night
includes taxes & fees
Luxury Lakefront home on Sebago Lake W/ Sandy Beach
Open floor plan.
Property grounds
Kitchen recently renovated.
Floors recently refinished.
Wonderful
(41 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
NZ$6,499
for 7 nights, 1 home
NZ$928 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Outdoor dining
Private kitchen
Private sandy beach area
Living area
Wonderful
(5 reviews)

Lakefront 15 mins from Portland with Private Beach and Fenced in Yard

Windham

20% off
NZ$8,833
for 7 nights, 1 home
NZ$1,262 per night
includes taxes & fees
Lakefront 15 mins from Portland with Private Beach and Fenced in Yard
Living area
Willard Beach
Dining
Master bedroom with queen bed and ceiling fan
Exceptional
(72 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
NZ$5,503
for 7 nights, 1 home
NZ$786 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Living area
Dining
Outdoor dining
Pool
Exceptional
(15 reviews)

Private Pool & Hot tub! Minutes to Sebago Lake! Nature! Perfect all year-round.

Windham

8% off
NZ$8,403
for 7 nights, 1 home
NZ$1,200 per night
includes taxes & fees
Private Pool & Hot tub! Minutes to Sebago Lake! Nature! Perfect all year-round.
Interior
Outdoor dining
Exterior detail
Private kitchen
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
NZ$4,921
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
picnic area
Casco Bay
Kitchen
WELCOME
Exceptional
(101 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
NZ$3,640
for 7 nights, 1 apartment
NZ$520 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Interior
Property grounds
Private kitchen
Interior
Exceptional
(10 reviews)

Peaceful Lakeside Oasis Near City Amenities

Windham

8% off
NZ$3,703
for 7 nights, 1 home
NZ$529 per night
includes taxes & fees
Peaceful Lakeside Oasis Near City Amenities
View from Roof Top deck
Looking up to the house from Garrison Cove
Dining Room Seating for ten, extra dining also available
Kitchen at night with setup for a dinner party
Exceptional
(86 reviews)

Amazing Views, and Comfortable Spaces in this Well Appointed Island Home

Bailey Island

8% off
NZ$10,552
for 7 nights, 1 home
NZ$1,507 per night
includes taxes & fees
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Living area
The stairs are wide and have a railing up to The Nest located on the 2nd floor.
Just steps away to LLBean, open 24 hours, 7 days/week all year long!
Private kitchen
Exceptional
(80 reviews)

The Nest ~ Quiet location close to shops, dining and Downtown Freeport.

Freeport

8% off
NZ$2,596
for 7 nights, 1 apartment
NZ$371 per night
includes taxes & fees
The Nest ~ Quiet location close to shops, dining and Downtown Freeport.
Living area
Marina
Private kitchen
Living area
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
NZ$3,175
for 7 nights, 1 apartment
NZ$454 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Room
Terrace/patio
View from living room
Private kitchen
Exceptional
(190 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
NZ$2,611
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Large open concept living space with tall sloped celling and a loft.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
NZ$4,889
for 7 nights, 1 apartment
NZ$698 per night
includes taxes & fees
Exchange Street Skylight Loft
Warm and inviting living room with gas fireplace
Lovely Craftsman-style details greet guests at the front door
Huge dining table and pass-through to kitchen
Open concept main floor with charming original Craftsman woodwork
Exceptional
(80 reviews)

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Portland

8% off
NZ$12,272
for 7 nights, 1 home
NZ$1,753 per night
includes taxes & fees
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Space for shoes and coats before going upstairs into the living space.
Walk around behind the garage to access the apartment.
Room
Your private deck and entrance.
Exceptional
(15 reviews)

Private studio nestled in woods outside Portland

Westbrook

13% off
NZ$2,672
for 7 nights, 1 apartment
NZ$382 per night
includes taxes & fees
Private studio nestled in woods outside Portland
Interior
Outdoor dining
Dining
Private kitchen
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
NZ$2,706
for 7 nights, 1 apartment
NZ$387 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Private kitchen
Living area
Interior
Room
Exceptional
(41 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

7% off
NZ$3,343
for 7 nights, 1 apartment
NZ$478 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Interior
Dining
Private kitchen
Outdoor dining
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

7% off
NZ$3,376
for 7 nights, 1 apartment
NZ$482 per night
includes taxes & fees
Fall In Love With Portland!
Exterior detail
Interior
Living area
Dining
Exceptional
(99 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
NZ$3,533
for 7 nights, 1 apartment
NZ$505 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Room
Scales in the Old Port for the best seafood
Interior
Discover Victoria Mansion at the bottom of the street.
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
NZ$3,373
for 7 nights, 1 apartment
NZ$482 per night
includes taxes & fees
Charming West End Hideaway. Private Parking
Living area
Coziest place to relax and unwind have a fire and enjoy the fall and winter
Exterior
Private kitchen
Exceptional
(67 reviews)

Clean, Cozy, and Professional Waterfront Home- minutes to Portland

Falmouth

8% off
NZ$7,192
for 7 nights, 1 home
NZ$1,027 per night
includes taxes & fees
Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Private kitchen
Property grounds
Room
Exterior
Exceptional
(32 reviews)

Vienna's Place

Freeport

8% off
NZ$2,754
for 7 nights, 1 apartment
NZ$393 per night
includes taxes & fees
Vienna's Place
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Cumberland getaway

Learn about the unique charm of Cumberland with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Cumberland

Are you searching for top things to see and do in the area? Venture out of your cosy holiday rental and experience everything that makes Cumberland a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Seacoast Adventure (10.4 mi / 16.7 km)
  • Brunswick Golf Course (15.8 mi / 25.5 km)
  • Gilsland Farm Audubon Center (6.3 mi / 10.1 km)
  • Riverside Municipal Golf Course (6.4 mi / 10.2 km)
  • Spring Meadows Golf Course (7.9 mi / 12.7 km)
  • Wilbur's of Maine Chocolate Confections (8.1 mi / 13 km)

Exploring the natural landscape of Cumberland

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Cumberland is a great place to get out in nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Desert of Maine (6.7 mi / 10.9 km)
  • Eastern Promenade (8.8 mi / 14.2 km)
  • East End Beach (8.9 mi / 14.3 km)
  • Sand Beach (9.5 mi / 15.2 km)
  • Little Sebago Lake (9.6 mi / 15.5 km)
  • Thompson's Point (10.2 mi / 16.5 km)

Travelling to and around Cumberland

The nearest airport is in Portland, ME (PWM-Portland Intl. Jetport), located 10.6 mi (17.1 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 17.5 mi (28.2 km) away.

Frequently asked questions

What is the best area to stay in Cumberland when booking a holiday rental?
When considering a holiday rental in Cumberland, Maine, the area around the picturesque village centre is highly recommended. This charming neighbourhood offers a delightful mix of residential comfort and local amenities, making it an ideal base for visitors. You'll find a range of properties available, from cosy cottages to spacious family homes, providing ample options to suit different preferences.One of the top attractions in the area is the scenic Twin Brook Recreation Area, which features beautiful trails for walking, running, and cycling, as well as areas for picnicking and enjoying the natural beauty of Maine. Additionally, the nearby Maine State Music Theatre offers a vibrant cultural experience, showcasing various performances throughout the summer season. Staying in this neighbourhood not only allows easy access to these attractions but also immerses you in the welcoming community spirit that Cumberland is known for.
When is the best time to visit Cumberland for a holiday rental?
September is the most popular time to visit Cumberland, Maine, as summer transitions into autumn. This period attracts both adventure seekers and families looking to enjoy the outdoors before the cooler months arrive. From July to September, the peak season is characterised by vibrant community activities, including local farmers' markets and outdoor festivals, which create a lively option.During September, visitors can enjoy mild temperatures ranging from 10 to 20 degrees Celsius, making it an ideal time for outdoor activities such as hiking, cycling, and exploring the scenic trails of the nearby Bradbury Mountain State Park. The stunning fall foliage begins to make its appearance, providing a picturesque backdrop for sightseeing and leisurely walks through the charming town.For those seeking a more budget-friendly option, consider planning your visit in November. While this month is quieter, it offers a unique opportunity to experience Cumberland's tranquillity and the beauty of the late autumn landscape. You can also benefit from lower holiday rental rates during this time, making it an appealing choice for a peaceful getaway.Ultimately, the best time to book a holiday rental in Cumberland depends on whether you prefer the bustling energy of the summer months or the serene beauty of autumn.
What are the top attractions in Cumberland?
In Cumberland, Maine, visitors can enjoy a variety of attractions amidst its scenic charm. The town is known for its beautiful parks, with the expansive Cumberland Town Forest offering trails for hiking and nature walks. Additionally, the nearby Royal River Park features lovely picnic areas and opportunities for fishing along the river.Cumberland is also home to the historic Maine State Music Theatre, where guests can catch a performance during the summer months. For those interested in local history, the Cumberland Historical Society provides insights into the area's past and hosts educational events.For outdoor enthusiasts, the nearby Maine Audubon's Gilsland Farm offers a chance to explore nature trails and engage in birdwatching, while the picturesque Falmouth Nature Preserve is just a short drive away, providing additional recreational options.
Are all fees included in the Cumberland holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Cumberland holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Cumberland with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Cumberland holiday homes?
You can find great discounts on holiday homes in Cumberland on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Cumberland holiday home booking on Bookabach?
To find Cumberland holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Cumberland?
A long-stay holiday home in Cumberland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Cumberland holiday home?
Book your Cumberland holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cumberland?
Prices for holiday homes in Cumberland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Cumberland to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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