Cumberland Foreside holiday rentals

We found 823 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Cumberland Foreside that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as parking and a fireplace. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Cumberland Foreside

Showing deals for:20 Nov - 27 Nov

Interior
Exterior
Property grounds
Interior
Exceptional
(11 reviews)

Beautiful farmhouse with hiking trails/kayaking. 5 minutes to town or ocean!

Freeport

8% off
AU$8,604
for 7 nights, 1 home
AU$1,229 per night
includes taxes & fees
Beautiful farmhouse with hiking trails/kayaking. 5 minutes to town or ocean!
Interior
Living area
Exterior
Dining
Exceptional
(20 reviews)

Entire House - three suites - conferences, reunions, retreats

Westbrook

8% off
AU$11,872
for 7 nights, 1 home
AU$1,696 per night
includes taxes & fees
Entire House - three suites - conferences, reunions, retreats
Interior
Terrace/patio
Private kitchen
Room
Wonderful
(24 reviews)

Beautiful, single story ranch. Next to city park with ocean view!

Portland

8% off
AU$8,769
for 7 nights, 1 home
AU$1,253 per night
includes taxes & fees
Beautiful, single story ranch. Next to city park with ocean view!
Interior
Outdoor dining
Private kitchen
The living room leads out to a private deck with a dining table that seats 4.
Exceptional
(42 reviews)

Modern & Sunny House Steps from the Promenade. Private Parking!

Portland

8% off
AU$3,932
for 7 nights, 1 home
AU$562 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade. Private Parking!
picnic area
Casco Bay
Dining area
WELCOME
Exceptional
(101 reviews)

Beautiful Oceanfront Apartment, scenic views and water access

Yarmouth

8% off
AU$2,933
for 7 nights, 1 apartment
AU$419 per night
includes taxes & fees
Beautiful Oceanfront Apartment, scenic views and water access
Living area
Master Bedroom
View from Master Bedroom
Dining
Exceptional
(33 reviews)

Amazing Oceanfront Brand NewHome Ideal location -

Peaks Island

8% off
AU$7,553
for 7 nights, 1 home
AU$1,079 per night
includes taxes & fees
Amazing Oceanfront Brand NewHome Ideal location -
Private kitchen
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!
High ceilings with exposed beams in every room. Cable TV in bedroom and living.
Exceptional
(80 reviews)

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

Freeport

8% off
AU$2,166
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
The Nest ~ Quiet location close to shops, dining and Downtown Freeport.
Interior
Interior
Room
Dining
Exceptional
(31 reviews)

Sunny Spot with Private Parking.

South Portland

8% off
AU$2,235
for 7 nights, 1 apartment
AU$319 per night
includes taxes & fees
Sunny Spot with Private Parking.
Dining Room Seating for ten, extra dining also available
Looking up to the house from Garrison Cove
View from Roof Top deck
Living Room Fireplace
Exceptional
(84 reviews)

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

Bailey Island

8% off
AU$8,497
for 7 nights, 1 home
AU$1,214 per night
includes taxes & fees
Amazing Views, and Comfortable Spaces in this Well Appointed Island Home
Private kitchen
Marina
Dining
Living area
Exceptional
(13 reviews)

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

South Portland

16% off
AU$2,559
for 7 nights, 1 apartment
AU$366 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Everyone's favorite room in the home. Massive 8ftx6ft skylight.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Massive 100 inch smart TV
View from inside unit.
Exceptional
(6 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,907
for 7 nights, 1 apartment
AU$558 per night
includes taxes & fees
Exchange Street Skylight Loft
Living area
Terrace/patio
View from living room
Private kitchen
Exceptional
(183 reviews)

1 room luxury ocean front studio cottage

Harpswell

8% off
AU$2,177
for 7 nights, 1 apartment
AU$311 per night
includes taxes & fees
1 room luxury ocean front studio cottage
Room
Walk around behind the garage to access the apartment.
Your private deck and entrance.
Private kitchen
Exceptional
(9 reviews)

Private studio nestled in woods outside Portland

Westbrook

13% off
AU$2,344
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Private studio nestled in woods outside Portland
Private kitchen
Living area
Interior
Dining
Exceptional
(133 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

12% off
AU$2,950
for 7 nights, 1 apartment
AU$421 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
Dining
Outdoor dining
Living area
Private kitchen
Exceptional
(11 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,208
for 7 nights, 1 apartment
AU$315 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Living area
Coziest place to relax and unwind have a fire and enjoy the fall and winter
Coffee/ Wine station
Private kitchen
Exceptional
(66 reviews)

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

Falmouth

8% off
AU$6,303
for 7 nights, 1 home
AU$900 per night
includes taxes & fees
Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Dining
Interior
Exterior detail
Living area
Exceptional
(99 reviews)

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

Portland

8% off
AU$2,847
for 7 nights, 1 apartment
AU$407 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Private kitchen
Property grounds
Interior
Room
Exceptional
(29 reviews)

Vienna's Place

Freeport

8% off
AU$2,325
for 7 nights, 1 apartment
AU$332 per night
includes taxes & fees
Vienna's Place
Interior
Scales in the Old Port for the best seafood
The State Theater is a 5 minute walk away.
Discover Victoria Mansion at the bottom of the street.
Exceptional
(53 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
AU$2,717
for 7 nights, 1 apartment
AU$388 per night
includes taxes & fees
Charming West End Hideaway. Private Parking
View from the top of the Portland Observatory.
Minato is a quick walk away.
Baharat, across the street from rising tide.
Open kitchen concept with a breakfast bar.
Exceptional
(140 reviews)

Adorable Portland getaway on the Eastern Promenade

Portland

12% off
AU$1,358
for 7 nights, 1 apartment
AU$194 per night
includes taxes & fees
Adorable Portland getaway on the Eastern Promenade
Floors recently refinished.
Property grounds
Kitchen recently renovated.
Living room has queen size pull out sofa bed.
Wonderful
(40 reviews)

Stover's Cove Beach Coastal Retreat

Harpswell

8% off
AU$5,236
for 7 nights, 1 home
AU$748 per night
includes taxes & fees
Stover's Cove Beach Coastal Retreat
Interior
Interior
Room
Walnut topped kitchenette counter with coffee maker.
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,220
for 7 nights, 1 apartment
AU$603 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Large, well-stocked Kitchen w/stainless steel counter and appliances
5 min car ride to Downtown/Old Port.
Mix of nautical and rustic elements throughout.
Large deck with seating for six, festive lighting and a firepit. Views and sun!
Exceptional
(131 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

6% off
AU$3,103
for 7 nights, 1 apartment
AU$443 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Room
Interior
Living area
Dining
Exceptional
(20 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,438
for 7 nights, 1 apartment
AU$634 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

  • 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

Choose a holiday rental for your Cumberland Foreside getaway

Learn about the unique charm of Cumberland Foreside with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Cumberland Foreside

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

  • Happy Wheels Skate Center (8.4 mi / 13.5 km)
  • Spring Meadows Golf Course (11.5 mi / 18.5 km)
  • Seacoast Adventure (14 mi / 22.6 km)
  • Len Libby Chocolates (14.7 mi / 23.6 km)
  • Brunswick Golf Course (15.2 mi / 24.5 km)
  • Gilsland Farm Audubon Center (4.2 mi / 6.8 km)

Exploring the natural landscape of Cumberland Foreside

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Cumberland Foreside is a great place to spend some time outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Winslow Memorial Park (5.3 mi / 8.5 km)
  • Eastern Promenade (6.6 mi / 10.7 km)
  • East End Beach (6.6 mi / 10.7 km)
  • Sand Beach (6.7 mi / 10.7 km)
  • Desert of Maine (7.2 mi / 11.6 km)
  • Willard Beach (8.1 mi / 13.1 km)

Transport to and around Cumberland Foreside

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 9.5 mi (15.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 20.4 mi (32.8 km) away.

Frequently asked questions

Where are the best areas for renting a beach house in Cumberland Foreside?
For renting a beach house in Cumberland Foreside, the picturesque waterfront along Casco Bay is an excellent choice. This area features a variety of holiday homes that offer stunning views of the water and easy access to sandy beaches. Many properties in this region come with desirable amenities such as private decks, outdoor grills, and spacious living areas, making them great for families or groups looking to enjoy seaside relaxation.In addition, the nearby town centre provides quaint shops and local dining options, enhancing the convenience for visitors. The proximity to scenic spots like the Cumberland Foreside Beach and the nearby Mackworth Island allows for leisurely walks and nature exploration. Rentals in this area often feature modern kitchens, comfortable bedrooms, and outdoor spaces that encourage enjoying the fresh coastal air after a day of beach activities.
What is the most popular type of holiday rental accomodation in Cumberland Foreside?
In Cumberland Foreside, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many also offer outdoor spaces such as decks or gardens, superb for enjoying the beautiful coastal scenery and fresh air.
Are there any family house rentals in Cumberland Foreside?
In Cumberland Foreside, Maine, there are several family-friendly house rentals available, making it an excellent choice for those seeking a getaway. The area features spacious homes that often include amenities such as fully equipped kitchens, ample living areas, and outdoor spaces for children to play. Many properties are located near the picturesque coastline, providing opportunities for beach outings and water activities.Visitors can explore nearby attractions like the scenic landscapes of Mackworth Island, great for family hikes, or the charming town of Falmouth, known for its local shops and dining options.
Can I rent a holiday home with a pool or hot tub in Cumberland Foreside?
In Cumberland Foreside, Maine, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque coastal area offers a serene atmosphere, with properties often set amidst beautiful natural surroundings, providing both relaxation and recreational options.Travellers can expect amenities such as private swimming pools and hot tubs, superb for unwinding after a day of exploring the local area. Many of these rentals also include outdoor spaces like patios or decks, fully equipped kitchens for home cooking, and comfortable living areas for family gatherings.
Are there pet-friendly house rentals in Cumberland Foreside?
In Cumberland Foreside, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. Many of these properties typically feature amenities such as spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups looking to enjoy a relaxing getaway.The neighbourhood is known for its scenic beauty and proximity to various parks and nature reserves, providing ample opportunities for outdoor activities with pets. Nearby, the picturesque local beaches and waterfront areas are superb for leisurely walks or playtime with your furry friends. Additionally, Cumberland Foreside boasts charming local shops and eateries, ensuring that you have everything you need during your stay.
Are there any remote work holiday rentals in Cumberland Foreside?
In Cumberland Foreside, Maine, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as high-speed internet, free Wi-Fi, and dedicated workspaces with desks and chairs, making them ideal for those needing to balance work and leisure.The area itself offers a peaceful coastal atmosphere, great for unwinding after a productive day. Nearby, you can enjoy scenic walks along the shore or explore local parks. The charming community also provides easy access to shops and dining options, ensuring that all your needs are met during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cumberland Foreside?
In Cumberland Foreside, popular rental amenities include proximity to the beach, allowing guests to easily enjoy the coastal scenery and activities. Many holiday rentals come equipped with coffee and tea makers, ensuring that travellers can enjoy a warm beverage at their convenience. Properties often feature decks or patios, providing outdoor spaces to relax and take in the fresh air. Expect dining areas in most rentals, suitable for sharing meals with family or friends. Additionally, kayaking opportunities are available nearby, offering adventurous guests a chance to explore the beautiful waterways of the region.
When is the best time to visit Cumberland Foreside for a holiday rental?
The best time to visit Cumberland Foreside for a holiday rental is during the peak season from May to July, with June being the most popular month. This vibrant period attracts travellers seeking to enjoy the coastal charm of Maine, where outdoor activities such as kayaking, sailing, and relaxing on the beach are at their best. With temperatures typically ranging from 15 to 25 degrees Celsius, visitors can indulge in pleasant weather while exploring the stunning shoreline and local parks.While June offers a lively option filled with events and activities, if you're seeking a more tranquil experience, consider planning your visit in April. This shoulder month features fewer tourists, allowing for peaceful strolls along the scenic coastline or visits to nearby attractions without the crowds. Plus, the early spring landscape begins to bloom, creating a picturesque backdrop for your holiday.Ultimately, your choice depends on whether you prefer the bustling energy of summer or the quieter yet equally enjoyable experiences in the early spring.
What are the top attractions in Cumberland Foreside?
In Cumberland Foreside, visitors can enjoy a serene coastal atmosphere with several attractions nearby. The picturesque Foreside Road offers beautiful views of Casco Bay, making it a lovely area for leisurely walks or cycling. The nearby Cumberland Town Forest is superb for hiking and nature walks, featuring trails that wind through lush woodlands.For those interested in maritime history, the Maine State Museum in Augusta, a short drive away, provides insights into the state's rich nautical heritage. Additionally, the charming village centre of Cumberland features local shops and eateries, where visitors can experience the community's unique charm. The proximity to the bustling city of Portland allows easy access to a wider range of attractions, including the iconic Old Port district and the Portland Head Light, a historic lighthouse located in Fort Williams Park.
Are all fees included in the Cumberland Foreside holiday homes prices shown on Stayz?
Stayz 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 Foreside holiday homes with parking?
Stayz offers a wide selection of holiday homes in Cumberland Foreside 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 Foreside holiday homes?
You can find great discounts on holiday homes in Cumberland Foreside on Stayz, 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 Foreside holiday home booking on Stayz?
To find Cumberland Foreside holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Cumberland Foreside?
A long-stay holiday home in Cumberland Foreside 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 Stayz?
Stayz'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 Foreside holiday home?
Book your Cumberland Foreside 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cumberland Foreside?
Prices for holiday homes in Cumberland Foreside 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. Stayz offers something for every taste and budget, from affordable homes in Cumberland Foreside to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.