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Cumberland, ME vacation rentals
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Best Vacation rentals and Airbnb offers in Cumberland, ME

Best family friendly Cumberland, ME vacation rentals

Among the 385 accommodations in Cumberland, ME, here are the 4 best family friendly rentals

Willard By The Sea #2 , Beachfront Living, Walkable Charm + Minutes To Portland - Cumberland, ME
9.6 5 reviews
Cumberland, ME
06/23 – 06/30
$705/nighttotal: $4935 (7 )

Willard By The Sea #2 , Beachfront Living, Walkable Charm + Minutes To Portland

2 3
apartment , South Portland
This South Portland apartment is located directly on Willard Beach, offering stunning ocean views and easy access to restaurants and shops. It has received excellent user ratings, making it a popular choice for travelers. The apartment features two bedrooms and one bathroom, comfortably accommodating up to four guests. It includes amenities like a fully equipped kitchen, air conditioning, a garden, a spa, and parking, making it an ideal choice for a relaxing and enjoyable stay.
Beautiful +Nostalgic + Coastal Maine Cottage - Cumberland, ME
9.7 222 reviews
Cumberland, ME
06/23 – 06/30
$406/nighttotal: $2842 (7 )

Beautiful +Nostalgic + Coastal Maine Cottage

1 3
apartment , Falmouth
This Falmouth vacation rental is located just a short distance from Casco Bay, offering easy access to the beautiful waterfront and nearby attractions like Gilsland Farm Audubon Center and Quarry Run Dog Park. It consistently receives excellent ratings for its cleanliness, location, and overall experience.
This 3-bedroom home comfortably sleeps up to 6 guests and includes a fully equipped kitchen, a private patio, and a barbecue grill. Enjoy the peaceful setting, take advantage of the free Wi-Fi, and explore the nearby attractions and outdoor activities.
The Gray Barn Loft - Cumberland, ME
10 5 reviews
Cumberland, ME
06/23 – 06/30
$374/nighttotal: $2618 (7 )

The Gray Barn Loft

1 3
farm , Yarmouth
This renovated 1878 barn loft, offering a unique lodging experience, is located beside quiet woods, a short walk (approximately 2,640 feet) from Yarmouth restaurants and shops, and near Maine's coastline, providing a peaceful retreat with rustic charm and proximity to woodland animals.
This farm stay accommodates up to 5 guests in 1 bedroom and 1 bathroom, featuring air conditioning, internet, a kitchen with a fridge, freezer, and microwave oven, and a garden, making it an ideal home base for exploring the area or for a romantic getaway.
Maine Island Vacation Cottage - Cumberland, ME
9.2 59 reviews
Cumberland, ME
06/23 – 06/30
$358/nighttotal: $2506 (7 )

Maine Island Vacation Cottage

1 3
apartment , Long Island
This charming cottage is located on Long Island, just off the coast of Portland, Maine, a two-hour drive from Boston, offering a peaceful escape from the hustle and bustle of everyday life. The cottage has consistently received excellent user ratings for its location and cleanliness, and a very good rating for overall experience.
The cottage has three bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy the rustic charm, oceanfront location, spacious outdoor area, and family-friendly amenities, including a Honda SUV and bikes for exploring the island.

Best Cumberland, ME vacation rentals with a pool

Among the 385 accommodations in Cumberland, ME, here are the 1 best rentals with a pool

Luxury Oceanfront Freeport On Casco Bay - Cumberland, ME
10 6 reviews
Cumberland, ME
06/23 – 06/30
$1809/nighttotal: $12663 (7 )

Luxury Oceanfront Freeport On Casco Bay

1 3
apartment , Freeport
This Freeport, Maine oceanfront house boasts five bedrooms and 3.5 bathrooms, minutes from downtown Freeport's shops, restaurants, L.L.Bean, and the Desert of Maine.
This spacious home offers beach access, ample parking, a full kitchen, Wi-Fi, and accommodates up to ten guests, perfect for families or groups exploring Freeport's attractions.

Frequently Asked Questions about vacation rentals in Cumberland, ME

  • What essentials should you bring along for a trip to Cumberland, Maine?

    Pack for all types of weather. Maine weather can be unpredictable, so layers are key. Comfortable walking shoes are a must, as exploring Cumberland on foot is a great way to see the town. Don't forget sunscreen, insect repellent, and a rain jacket, especially during the warmer months. A camera is also a must to capture the beautiful scenery.
  • What are the best Airbnb and vacation rentals in Cumberland, ME?

    Loft Apartment On Tree-lined Street In Falmouth, Cottage Under A Crabapple Tree and Falmouth 3br Near Town Landing are the most popular Airbnb and vacation rentals in Cumberland, ME among travelers.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Cumberland, Maine?

    A daily budget in Cumberland will vary greatly depending on your travel style. Accommodation can range from budget-friendly motels to more upscale hotels. Food costs will depend on your dining choices; expect to spend $25-$50 per day on food. Transportation costs will be minimal if you're walking or using ride-sharing services. Activities are generally free or low cost, such as walking the trails or enjoying the views from the Chebeague Island Ferry terminal. A reasonable daily budget could range from $100 to $250 per person, depending on your choices.
  • What are the most popular Airbnbs in Cumberland, ME?

  • Where can you find the best restaurants serving local dishes in Cumberland, Maine, and what are the must-try specialties?

    Cumberland has a variety of restaurants. While there aren't specific 'must-try' local dishes unique to Cumberland, many restaurants feature fresh seafood, a Maine staple. You'll find various options, from casual diners to more upscale establishments. Checking local reviews online will help you find restaurants that suit your taste and budget.
  • What are the best vacation rentals with a pool in Cumberland, ME?

  • What are some less-famous attractions in Cumberland, Maine, that are worth the visit?

    The network of walking trails throughout Cumberland offers a peaceful escape. Exploring these trails provides a chance to see the town from a different perspective and enjoy the natural beauty. Many of these trails lead to the Presumpscot River, offering scenic views. The various smaller parks scattered throughout the town also offer quiet places for relaxation and reflection.
  • What are the best rentals for families and kids in Cumberland, ME?

  • What are the best activities for engaging with locals and understanding their culture in Cumberland, Maine?

    Attending local events, if any are scheduled during your visit, is a great way to meet residents. Striking up conversations with staff at local businesses can also provide insights into the community. Simply taking a stroll through the town and observing daily life can offer a good sense of Cumberland's culture.
  • What are the best rentals or Airbnbs with a jacuzzi in Cumberland, ME?

  • What unique natural landscapes and terrain features can travelers explore in Cumberland, Maine?

    Cumberland's natural beauty is primarily found in its coastal location and its network of walking trails. The Presumpscot River runs through the town, offering scenic views and opportunities for kayaking or canoeing. The proximity to Casco Bay provides access to beautiful coastal scenery.
  • How many days are ideal for visiting Cumberland, Maine, and what are some itinerary suggestions?

    A single day is sufficient to explore Cumberland's main attractions. However, extending your stay to two days would allow for a more relaxed pace and the opportunity to explore the walking trails and enjoy the natural scenery more thoroughly. A possible itinerary could include exploring Main Street's historical houses, visiting the Chebeague Island Ferry terminal, and walking along the Presumpscot River.

Nearby regions

Best Cumberland, ME vacation rentals with a balcony

Tideview Estate - Cumberland, ME
Cumberland, ME
06/23 – 06/30
$791/nighttotal: $5537 (7 )

Tideview Estate

4 3
house , Cumberland
This Tideview Estate rental house is located in Yarmouth, 9 miles from Portland Observatory and 9.5 miles from Merrill Auditorium.
This 2940 square foot house offers accommodation for 15 guests with four bedrooms, three bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, a hot tub, a terrace, an outdoor dining area, a picnic area, and on-site restaurant access, with Funtown Splashtown USA 22 miles away and Aquaboggan Water Park 21 miles away.
The Bow Street Abode / Charming 2 Br Retreat - Cumberland, ME
10 17 reviews
Cumberland, ME
06/23 – 06/30
$323/nighttotal: $2261 (7 )

The Bow Street Abode / Charming 2 Br Retreat

2 3
apartment , Freeport
This Freeport apartment rental is conveniently located within walking distance of L.L.Bean, shops, restaurants, and the Amtrak Downeaster station, offering easy access to Casco Bay and nearby state parks.
The two-bedroom, one-bathroom unit features a fully equipped kitchen, in-unit laundry, and a terrace, comfortably accommodating up to four guests and providing easy access to Mast Landing Sanctuary and Wolfe's Neck Woods State Park.
Wonderful  Portland Waterfront Home - Cumberland, ME
9.6 34 reviews
Cumberland, ME
06/23 – 06/30
$753/nighttotal: $5271 (7 )

Wonderful Portland Waterfront Home

2 3
apartment , Portland
This vacation rental is located in East Deering, a short distance from Casco Bay, Eastern Promenade, and Mackworth Island, offering easy access to Portland's attractions and natural beauty. Guests consistently rate this property excellent, highlighting its peaceful garden and comfortable accommodations.
This two-bedroom house spans 1400 square feet and comfortably accommodates up to four guests. Enjoy modern amenities like free WiFi, a balcony, and a fully equipped kitchen with a refrigerator, oven, stovetop, and dishwasher.

Best Cumberland, ME vacation rentals with parking

Modern Waterfront Apt With Bay Views - Cumberland, ME
10 4 reviews
Cumberland, ME
06/23 – 06/30
$442/nighttotal: $3094 (7 )

Modern Waterfront Apt With Bay Views

1 3
apartment , Falmouth
This 1-bedroom waterfront condo in Falmouth Foreside offers direct views of Casco Bay and Mackworth Island, located just a 5-mile drive from downtown Portland.
This apartment features a private deck, a fully equipped kitchen with stainless steel appliances, air conditioning, and garage parking, accommodating up to 3 guests.
Oceanfront Cottage On Casco Bay In Yarmouth - Cumberland, ME
Cumberland, ME
06/23 – 06/30
$1807/nighttotal: $12649 (7 )

Oceanfront Cottage On Casco Bay In Yarmouth

1 3
apartment , Yarmouth
This renovated coastal cottage in Yarmouth offers direct access to Casco Bay, putting you on the Maine shoreline with swimming at high tide and provided paddleboard and kayak for your use.
This 2-bedroom, 1-bathroom rental accommodates up to 5 guests and features a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and extensive outdoor deck space.
Seaside 4 Bedroom, 1 Bath Cottage! - Cumberland, ME
9.5 4 reviews
Cumberland, ME
06/23 – 06/30
$586/nighttotal: $4102 (7 )

Seaside 4 Bedroom, 1 Bath Cottage!

4 3
apartment , Falmouth
This Falmouth Foreside vacation rental boasts a beachfront location with direct beach access, a 15-minute walk from Casco Bay, and within 3 miles of Sturdivant Island and the Gilsland Farm Audubon Center.
This four-bedroom, one-bathroom home sleeps seven guests and features a fully equipped kitchen, private balcony, free WiFi, a swimming pool, spa, and fitness center; enjoy nearby attractions and on-site amenities.
Cute 2+ Bedroom Cottage - Cumberland, ME
9.0 23 reviews
Cumberland, ME
06/23 – 06/30
$180/nighttotal: $1260 (7 )

Cute 2+ Bedroom Cottage

3 3
cottage , Portland
This charming cottage is located near the beach in Portland, within a 10-minute walk of Casco Bay, Umbrella Cover Museum, and Fifth Maine Museum, making it a convenient base for exploring the city. It has received excellent user ratings, so you can be sure of a comfortable and enjoyable stay. This cozy home offers three bedrooms, a sofa bed, and ample space for up to six guests. You'll have access to amenities like a fully equipped kitchen, a garden, and barbecue grills for outdoor dining and relaxation.
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