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Vacation rentals in Cumberland County

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Top-rated vacation rentals in Cumberland County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Romantic Cottage on Collins Pond in Windham
Entire cottage · 2 guests · 1 bed · 1 bath

Romantic Cottage on Collins Pond in WindhamCollins Pond Cottage is the ideal venue to enjoy a relaxing getaway together. Awaken to stunning sunrises then lounge on the secluded deck. Steps from door to shore, there's a dock with kayaks, paddleboat and a canoe, to explore the 42 acre pond. Inside, the full kitchen is well appointed and the livingroom is comfortable and spacious. Upstairs, bedroom French doors open to an intimate balcony for two. Fireplaces and soothing water views add charm to the cottage. No pets or parties.

Cottage Under a Crabapple Tree
Entire guesthouse · 3 guests · 2 beds · 1 bath

Cottage Under a Crabapple TreeSteps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

The Studio
Private room · 2 guests · 1 bed · 1 private bath

The StudioLarge, beautiful room with private entrance (entry code provided) and private full bathroom. Great view of 9 private wooded acres with trails, abutting 1000 acre wildlife preserve (Morgan Meadows, part of Rachel Carson Wildlife Refuge). Within 20 minute drive of 6 lakes, 2 state parks, 3 public golf courses and one casino. Hosted by professional musician with performance career spanning 4 decades and 5 continents - private concerts available for additional fee, schedule permitting.

Vacation rentals for every style

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Popular amenities for Cumberland County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Cumberland County

  1. Entire guest suite
  2. Cumberland
Springer Park!! Adorable guesthouse with kitchen and all new everything!!
  1. Entire guest suite
  2. Cape Elizabeth
Serene by the Sea
  1. Entire guesthouse
  2. Naples
Long Lake Waterfront Cabin
  1. Farm stay
  2. Sebago
Vibrant Mt View Orchard Cottage
  1. Bus
  2. Gray
Cozy Converted Bus Close to Trails & Portland
  1. Entire cabin
  2. Harrison
Log Cabin in Maine’s Lakes and Mountains Region
  1. Private room
  2. Windham
Waterfront Suite with Patio minutes from Portland
  1. Entire cabin
  2. Windham
Highland Lake Hideaway minutes from Portland!
  1. Entire cabin
  2. Standish
Sebago Lake Waterfront Camp
  1. Entire cottage
  2. Pownal
Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike
  1. Entire cottage
  2. Brownfield
Unique, private, tranquil water front home.
  1. Tiny house
  2. Durham
Crow’s Nest Tiny House at Old Crow Ranch

Top-rated things to do in Cumberland County

Unique activities hosted by local experts vetted for quality

  • Goat Milking & Morning Chores
    You'll join Margaret and Karl for daily morning chores on Ten Apple Farm. We'll start the morning on the back porch with a light breakfast of homemade scones or biscuits, coffee, tea and juice and other farm goodies. Over breakfast we'll introduce the farm, talk about our journey to farming, and our experiences over the past 16 years on the farm. After breakfast we'll teach you how to milk goats! We raise French Alpine dairy goats, and milk 3-4 goats by hand twice a day, every day -- something we've been doing for 14 years. You'll learn how to milk, and help us feed the goats their breakfast of hay and grain. On our diversified farm, we have lots of animals in addition to the goats... miniature horses, pigs, sheep, chickens, ducks, and turkeys. We'll tour the farm, including our large kitchen garden, feeding and watering all the animals and talk about their care and the role each one plays on our diversified homestead. We'll spend some time grooming our two miniature horses, and weather permitting, we'll put the goats (with Philip, our sheep,) out in their pasture, and take the horses for a short walk around the farm. Other things to note: We'll be doing farm chores, so you might get dirty -- we'll do our best to keep you as clean as you want, if you just want to observe and chat, or let you get your hands dirty as much as you want. It's totally up to you!
    From Price:$32/person
  • Hands On With Magical Miniature Horses
    We will meet for a short orientation while you enjoy a welcoming coffee or cold drink. We will then introduce you to "the herd" and select a few horses to demo how to approach them, halter and lead them, groom them. You will then be helped to choose your own horse for the day. If the weather is cooperative, we can go for a short trail walk and perhaps see some of the wildlife who seem to be more comfortable and come closer when we humans are attached to a horse! Q and A is ongoing. All questions are welcome, and we will make every effort to gear the experience to the guests' individual interests. Some may simply want the 'therapy value' of touching and communicating. Some may want information on how we care for the horses. Some may want a demo on how we show them in competition. Energetic guests may want to take a horse over a set of appropriately scaled jumps or obstacles. All can be arranged, and everyone in the group can do something different, as long as I can maintain my ability to be six places at once. It's a talent. We can also provide a special occasion for any age guest and his or her celebrants, with appropriate refreshments that you bring along or order here. Other things to note Please dress appropriately for the weather. Closed-toe shoes, please. Sunscreen and bug repellent are handy seasonally. THE MAGICAL MINIS EXPERIENCE MAKES A FABULOUS, ONE OF A KIND GIFT!
    From Price:$38/person
  • Hiking with Goats
    A Ten Apple Farm goat hike is a two hour recreational and educational goat experience. You'll meet your hosts (and our herd of Alpine dairy goats), and hear about their 16 years of experience with goats and living on a small family farm. Once we've met the goats and the many other animals residents of the farm, we’ll set off on a hike through the Ten Apple Farm woods with the goats and Philip our sheep! The hike consists of an approximately one and a half mile loop trail through our woods on lightly groomed trails. Along the way we’ll talk about goats as pack animals, what they eat, and you’ll learn a thing or two about raising and caring for goats. There's lots of time for interacting with the goats, asking questions, or just soaking in the Maine woods and these adorable, fun animals. We end the experience with fresh goat milk and homemade cookies! Please note: Children must be at least 5 years old and accompanied by an adult. 5 and 6 year olds should plan to hold a parent's hand during the hike. (Children under 4 must be carried). Other things to note: The hike is not strenuous, but there is a little bit of steep terrain in 2 spots. We have rope railings on the trail to assist with getting up and down in those spots, but guests who have bad knees, hips, or other difficulties with uneven or steep terrain should be aware.
    From Price:$28/person
  • Portland & Peaks Isle Bike & ferry trip
    We will start by sizing you up on the bikes at the first Civic monument at Portland’s East End. Once we are ready; we will take a warm up roll on the scenic eastern promenade trail. We will take a brief tour of the waterfront warfs, then roll up through the old port towards Congress street. When we reach Congress we will talk about Portland history and architecture while taking a leisurely stroll through the Victorian west end. When we reach the western promenade; we'll start heading back towards the port where we will catch the ferry towards peaks island! Aboard the ferry we can talk some maritime history and enjoy a beverage before we hit the island. After our beer break ends on the ferry; we will take a beautiful and scenic ride around the island while telling stories about the island's unique history and place within the city of Portland. Our outing will end on the island before we head back to the peninsula! Other things to note We will be gone about 3-4 hours and won't eat until the end, so bring snacks
    From Price:$118/person
  • Guided mountain biking excursions
    My experience begins at the Sewall Woods recreational area, where guests are provided hard tail mountain bikes and helmets. I’ll explain how your bikes works and give tips along the way for those newer to trail riding. At Sewall woods we have about 4 miles of single track, mountain biking trail, through a quiet heavily wooded area. Once we’ve completed Sewall we will continue to the Fernald Station singletrack off the Cotton Valley railtrail. Here the trail rambles along the Wiley Brook for a mile or so, before winding back into the woods, for a few more miles of twisty singletrack. After we’ve completed our ride, I’m glad suggest places to eat of other fun things to do in the area. Other things to note Timing is flexible, let me know what works for you. Bikes ARE provided Please wear comfortable exercise clothing
    From Price:$76/person