Vacation Rentals By Owner In Oakland, ME

If you have a dog please check that you are paying for them when you are booking. If you and your family enjoy relaxing by the fire next to the water watching the fish jumping the eagles soaring and wonderful sunsets this is the place for you. You can enjoy fishing from the dock or one of the boats for some of the ponds many fish. There is a public boat launch in the cove and we have a boat mooring at the camp.br We allow more than four guests overnight for a fee of $40 per person per night up to six people total in the camp.br We allow a maximum of two dogs with a fee of $25 per night per dog. We will charge a fee of $100 if pets are not paid for up front the regular pet fee.br East pond his part of the Belgrade lakes chain and has a maximum depth of 27 feet it is 1,717 acres large and has 13.9 mi of shoreline for fishing and exploring. The camp will be closed from mid October to April 1st

Cottage

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(16)

$319.07

Welcome to our charming Vrbo home, a classic 1940s New Englander nestled in the heart of Central Maine; a stone throw from Colby College. This cozy retreat offers a perfect blend of vintage charm and modern comfort, providing an authentic experience for your stay. Step inside to discover a warm and inviting interior adorned with quaint touches and thoughtful decor.brbrOur spacious living area invites you to unwind in the living room after a day of exploration, while the fully equipped kitchen boasts all the amenities needed to whip up delicious meals with ease. Upstairs, comfortable bedrooms promise a restful night's sleep, ensuring you wake up refreshed and ready to embrace another day of adventure. With high-speed internet access and plenty of electrical outlets, you'll have everything you need to stay connected and productive during your stay. Step inside our French Door home office and catch up on emails, attend virtual meetings, or dive into creative projects, our office provides the perfect environment to get work done efficiently. No need to blur your background!brbrOutside, you'll find a serene backyard where you can enjoy al fresco dining, relax with a book, or simply soak in the tranquility of the surrounding landscape. Conveniently in Central Maine, our Vrbo home serves as the perfect base for exploring the region's natural beauty, state and national parks, charming towns, and outdoor activities.brbrWhether you're seeking a peaceful retreat or a home base for your Maine adventures, bringing your Colby Student to dinner or watching their game, our 1940s New Englander offers the ideal blend of comfort, convenience, and nostalgia for an unforgettable getaway. Book your stay with us today and experience the magic of Central Maine firsthand!

Private Vacation Home

4 be Updated home near Belgrade Lakes

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(18)

$160.23

Escape to one of our two sister A frames. This cozy cottages are nestled in the Oakland, Maine woods. Close proximity to Messalonskee and prestigious Belgrade Lakes you will find home to a wide variety of wildlife and nature. brbrOutside space includes two cozy chairs, a fire pit, small grassy area, small grill, private walking trail thru the woods, some playground equipment, and a disc golf goal. Please bring your own discs.brbrThere is one parking spot in front of the cabin, two smaller vehicles may fit. There is additional parking available as well if you are bringing two trucks or a trailer, please let us know and we can direct you.brbrThe campus includes a loft with a view, walking trail, free/overflow parking! A luxury, campy feel makes this A frame a perfect getaway for you and your family.

Sister A Frame in the Woods

Oakland, Maine, United States

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Bath

Sleeps

$308.97

Loon CovebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrSpend a quintessential summer in Maine at this darling lakefront cottage on the shores of McGrath Pond. Once featured on Magnolia Network's 'Maine Cabin Masters,' this home has been lovingly restored as a family gathering space. brbrThis picturesque abode sits near the northeastern corner of McGrath Pond, a spring-fed body of water that flows into Salmon Lake and the five other interconnected Belgrade Lakes. It's a beautiful setting for swimming and kayaking, taking afternoon naps in the hammock, and roasting marshmallows around the firepit at the water's edge. Two kayaks and two paddleboards are provided, so feel free to have adventures on the water and the home's boat slip. Oakland is two miles east while bustling Waterville and renowned Colby College are about four miles beyond.brbrEnter through a beautiful side deck, where you can barbecue in the afternoons, dine alfresco at sunset, and relax in the evenings while listening to the call of the loons. Inside, the cottage was renovated in a way that kept its charms intact, offering lofty ceilings, exposed crossbeams, and natural wood at every turn. Central heat and air-conditioning ensure comfort all year long. brbrThe living space is lined with windows, allowing you to admire the view of the lake whether you're cooking in the open kitchen, chopping vegetables on the island, or kicking back on the sofas to play cards or stream movies. Two inviting bedrooms, a sleeping loft, and complimentary WiFi, are also provided.brbrSHARED AMENITIESbr-Gas grillbrbrTHINGS TO KNOWbrStreaming services are available with guests' own account(s).brbrParking notes: There is free parking available for 5 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(13)

$288.85

Lenas' Lakeside CabinbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled upon Messalonskee Lake in the heart of the Belgrade Lakes region, you’ll find this classic Maine cottage. In the warm months, there’s room to park your boat and trailer at the property, and a public boat launch is a mile-and-a-half away. Golf, disc golf, music venues, a world-class museum, and fantastic local restaurants await in and around Waterville and Oakland. Portland, with a major jetport and bigger city attractions, is less than an hour and a half away.brbrAt the cottage itself, start the day on your screened porch with a cup of coffee, enjoying the lake view. Then take a swim or float on beautiful Lake Messolonski (Snow Pond) just outside your door. Inside, you’ll find a lofted space with hardwood floors, pine-paneled ceilings and walls, and all the cabin coziness you crave. Whip up a snack or quick meal in the spacious kitchenette, which features a fridge, brand new oven, and microwave, then grab a bite at one of the barstools. After a day of exploration, relax with a little streaming TV, upload the day’s pics to to social media with the free WiFi, or just unplug outside with a gorgeous sunset view over the water. End the night roasting marshmallows around the firepit - another perfect lake day awaits tomorrow.brbrTHINGS TO KNOWbrPlease respect the 3-adult maximum occupancy, which includes visitors.brThis unit is unsuitable for larger gatherings.brThere is a ladder that guests must climb to the loft with Queen sized bed. Downstairs has a sleeper sofa bed that sleeps one.brGuests must use their own credentials for streaming services.brThis vacation rental is not equipped with air-conditioning.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 2 vehicles.brbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(4)

$262.57

Lucky WatersbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your beautifully renovated apartment, tucked above a charming barn/garage in picturesque Oakland, ME! This inviting retreat blends rustic charm with modern comforts, making it an ideal escape for families, couples, or adventure seekers. Enjoy direct waterfront access and a variety of water activities, including kayaking, paddleboarding, and swimming. Plus, your four-legged friends are welcome in this dog-friendly space!brbrInside, you’ll find a cozy living area, a fully equipped kitchen with modern appliances, and a dining space perfect for shared meals. Relax by the front windows with lovely lake views, or make your way down to the gazebo and firepit area by the water for magical evenings under the stars. With central air conditioning, WiFi, and cable TV, you’ll have all the comforts of home during your stay.brbrThe surrounding area offers plenty to explore, from scenic hikes and fishing spots to charming local shops and restaurants. Whether you’re looking to unwind by the lake or embark on an outdoor adventure, this apartment is the perfect home base for experiencing the natural beauty of Oakland. Book your stay today and create unforgettable memories in this serene lakeside retreat!brbrThings to knowbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brThis rental is located on floor 2.brbrDock details: Guests may use one side of the dockbrbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Apartment

Charming apartment with waterfront access, modern comforts, and lakeside firepit

Oakland, Maine, United States

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Bath

Sleeps

$199.83

Your Oakland adventure begins at this perfect 1-bedroom condo. The space offers a peaceful retreat with cozy heating to keep guests comfortable year-round. A clean, well-appointed bathroom adds convenience to your stay. Whether you’re relaxing indoors or exploring nearby, this gorgeous condo provides a welcoming base. You’re sure to make fantastic memories with a stay at our place.

Condo

Fantastic 1-bdrm condo on Snow Pond in charming Oakland perfect for a getaway.

Oakland, Maine, United States

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Bath

Sleeps

Exceptional(45)

$272.83

Come and relax at this lakeside log cabin on pristine East Pond in Maine’s Belgrade Lakes. Enjoy the water, trails, local fun and call of the loons during the summer, the fall colors and crisp weather in autumn, and cross country and snowmobile trails in the winter. brbrThis fully- furnished modern two bedroom cabin sleeps six with three floors connected by a spiral stairwell. Towels and linens provided. The main floor’s living and dining room looks out across the lawn to the lake with a deck for grilling and outdoor dining. The kitchen has modern appliances including a dishwasher and both drip and pod coffee makers. The water is well-supplied and potable. The main floor bathroom has a toilet, shower and houses the washer and dryer. The upstairs bedroom offers a stunning view of the lake with queen, single and trundle beds, half bath and walk in closet. The downstairs bedroom has a queen, work/desk space, a walk-in closet and direct access to the lakeside yard. The cabin operates on a septic system and has radiant heat in the floors and an AC/heat pump in the upstairs loft. Wifi is available, and the TVs on each level offer on-demand streaming services. brbrThe cabin offers a private dock and swim raft, two kayaks and two SUPs along with life jackets (2 adult, 2 youth, 1 child)brbrSituated 15 minutes from I-95, the cabin is 30 minutes from Augusta, 20 minutes from downtown Waterville and Colby College, and just a few minutes from Camps Manitou, Matoka and Somerset. The is parking for 2 cars. Maximum number of guests: 6

Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes

Oakland, Maine, United States

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Bath

Sleeps

$240.89

Make yourself at home in our comfortable and private upstairs apartment over an oversized 3 bay garage.brFully furnished and ideal for 1 couple with this one bedroom apartment. There is a extra bed in the corner of an open area that’s not private for an extra guest or if you want to sleep separately.brOur Central Maine Town of Oakland offers four seasons of fun all within minutes of our location!brbrThese include~brSnowshoe-Walking- Hiking brSnowmobile trailsbrFishing – BoatingbrGolfingbrShoppingbrLocal WinerybrWaterville Opera HousebrGreat RestaurantsbrFarmers MarketbrAugusta Civic Center brbrGuests have a full kitchen, washer & dryer, free Wi-Fi, and all the amenities of home. Our furnishings include a queen size bed in private bedroom as well as a full size daybed off the living room, a workspace with a desk and plenty of areas for relaxing downtime. brbr***No smoking, vaping or illegal substances on premises. No unregistered guests. brNo Pets***

Apartment

Central Maine Apartment offering 4 Seasons of Fun.

Oakland, Maine, United States

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Bath

Sleeps

Most popular vacation rentals in Oakland

$313.38

Classy AF Home Steps from Colby and Trails

Oakland, Maine, United States

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Bath

Sleeps

$160.23

Sister A Frame in the Woods

Oakland, Maine, United States

Bed

Bath

Sleeps

$176.04

Sister A-Frame in Woods B

Oakland, Maine, United States

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Bath

Sleeps

$180.75

Quaint Little Cottage

Oakland, Maine, United States

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Sleeps

$184.80

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

Oakland, Maine, United States

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Sleeps

$185.30

Discover Oakland charm near Colby College 10 min

Oakland, Maine, United States

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Bath

Sleeps

$240.89

Apartment

Central Maine Apartment offering 4 Seasons of Fun.

Oakland, Maine, United States

Bed

Bath

Sleeps

$272.83

Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes

Oakland, Maine, United States

Bed

Bath

Sleeps

$435.02

Guest house

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

Oakland, Maine, United States

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Bath

Sleeps

$417.47