Home Vacation Rentals By Owner In Oakland, ME

Showing 20 Of 30 Vacation Rentals
Slider Thumb
Exceptional(23)

$417.47

/ Nightly
Private Vacation Home

Lake Front with Amazing Sunsets on McGrath Pond

Oakland, Maine, United States

Come enjoy a peaceful, lakeside retreat at Camp Ohana! Bring friends and family to hear the loons at night and watch the eagles soar during the day. This four bed, two bath home, with 100 feet of lake front and a large private dock, is perfect for families of all sizes! Perfectly situated in Oakland, Maine, this lake front house is an easy drive and convenient location for anyone looking to get away!brbrWeekly rentals are enforced during the summer season, Saturday to Saturday. We apologize that we are unable to accommodate early or late check-in or alternate check-in/check-out days.brbrThis picturesque lake front camp is perfectly set up to accommodate family and friends! We are so excited to share our family home with you. Come and stay awhile!brbrOriginally purchased by “GrandMom and Pop” in 1973, this camp has been enjoyed by four generations. The most recent major renovations took pace in 2020. The main floor has laminate flooring, overstuffed sectional couch and a 65 smart TV. The spacious family room boasts a 180 degree view of the lake front, as well as custom wood furniture from a local craftsman (Lovejoy Rustic Furniture)! The main floor bathroom had the tub/shower replaced in 2026. The basement includes a large living room that doubles as a fourth bedroom, with a second full bathroom and laundry room. brbrAC and heat have been installed throughout every level of the house, keeping you at the perfect temperature in both the summer and fall! The AC and heat units include the iWave-M Flexible Air Cleaner. These enhanced units kill mold, bacteria, and viruses. Additionally, they reduce allergens, odors, static electricity, and airborne particles. brbrOutside, enjoy the expansive dock and lake views. Enjoy four kayaks, canoe, two stand up paddle boards, and fishing gear included in the price of your stay. A variety of life jackets in sizes for infants, kids, and adults are provided for lake safety. After a day on the lake, sit around the picnic table and have a BBQ on the gas grill. Enjoy the fire pit while roasting marshmallows. The house is oriented for perfect sunsets every night. Pour yourself a nice glass of wine or Maine craft beer and enjoy the view!brbrCheck-in: 4 PMbrCheck-out: 10 AM brbrPlease Note: Basic bedding, towels, hand soap, and kitchen utensils are provided. We kindly ask that you bring your own shampoo, conditioner, body wash, and pantry items.brbrBedroom #1: Main floor near kitchen, queen bedbrBedroom #2: Second floor loft (no door), queen bedbrBedroom #3: Second floor (door), queen bed, toddler bed, ottoman with twin-sized pull outbrBedroom #4: Walk out basement, couch with queen-sized pull out (Private bathroom!)brbrBathroom #1: Main floor, full bath with tub/shower combobrBathroom #2: Walk out basement, full bath with walk-in showerbrbrGuests are expected to follow the check out procedures. If the check out procedures are not followed and the cleaning company feels that excessive cleaning is required, an additional $100 fee will be charged to the guests.brbrOutdoor amenities: br- Dock (early May and October bookings, dock might not be available)br- Gas BBQ grillbr- Picnic tablebr- Fire pit (firewood provided)br- Fishing polesbr- Tackle boxesbr- FOUR kayaksbr- TWO stand-up paddleboardsbr- Canoebr- Life vests (ranging from infant/child to adult sizes)br- Oversized dock with seating area (large enough for a rented motorized boat)br- Swimming floatbr- Sandy wading areabr- Large yardbr- Adirondack chairsbr- Child-sized Adirondack chairsbr- Cornhole boardsbr- Lobster potbrbrIndoor Amenities:br- Heat & AC Units throughout the campbr- Dishwasherbr- High speed WIFI suitable for working from home (supports multiple people & video calls)br- 65 Smart TV with YouTubeTV provided (or enjoy your own streaming service subscriptions)br- Games, books, BluRay DVD player & DVD selectionbr- Overstuffed sectional couchbr- Bath towelsbr- Beach towelsbr- Bath matsbr- Hand/dish towelsbr- Sheets, blankets, pillowsbr- Dining table with seating for 6br- Breakfast bar with seating for 2br- Coffee table with raising/lowering top (suitable for working from home or dining for 2)br- Pots/pansbr- Dishes/ glassware/ silverwarebr- Toasterbr- Drip coffee maker (filters provided, no creamer or sugar provided)br- Knife block/ cutting boardbr- Hand soap br- Laundry basketbr- First aid kit (located in the bathroom)br- Fire extinguisher (located in the pantry)br- Fans in each bedroombrbrA guide for local food, shopping, and other outdoor activities is provided in the Welcome Binder at Camp Ohana.
Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Slider Thumb
Exceptional(8)

$130.89

/ Nightly
Apartment

Oakland Apt on Messalonskee Lake w/ Dock Access!

Oakland, Maine, United States

Come for the lake and stay for the views at this Oakland, Maine, vacation rental! Nestled beside Messalonskee Lake, this 1-bedroom, 1-bathroom apartment sits within 4 miles of Colby College and has everything you need for a hassle-free stay. Prepare homemade favorites in the full kitchen, cool off inside the air-conditioned interior after hanging out under the sun, and splash into the water from the shared dock. Afterward, head inside for a movie night by the Smart TV.brbr-- THE PROPERTY --brbrFree WiFi | Shared Deck | Self Check-In brbrBedroom: Queen BedbrbrSHARED AMENITIES (first-come, first-served): Dock, boat launch, Messalonskee Lake access, yard, 1 kayakbrMAIN FEATURES: Smart TV, dining table, ceiling fan, lakefront viewbrKITCHEN: Dishwasher, drip coffee maker, toaster, slow cooker, fridge, stove & oven, microwave, dishware/flatware, trash bags/paper towels, cooking basics, spicesbrGENERAL: Central A/C & heat, washer & dryer, towels/linens, complimentary toiletries, iron & board, hair dryerbrFAQ: No fence before lakebrACCESSIBILITY: Single-story apartment, exterior staircase to enterbrPARKING: Shared driveway (1 vehicle)brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, each with a separate nightly rate. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrMESSALONSKEE LAKE (on-site): Swimming, paddleboarding, kayaking, boating, fishingbrOUTDOOR REC: Quarry Road Trails (7 miles), French Mountain (14 miles), Titcomb Mountain (31 miles), Androscoggin Riverlands State Park (42 miles)brTHINGS TO DO: Colby College (4 miles), Thomas College (5 miles), Colby College Museum of Art (5 miles), Maine State Museum (18 miles), DEW Haven | Maine Zoo & Rescue (21 miles)brAIRPORT: Portland International Jetport (75 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- NOTE: The hair Dryer, iron board, and iron available upond requestbr- NOTE: The property may not be suitable for children due to the unfenced lake and the property's sloped terrain; adult supervision is recommendedbr- NOTE: This single-story apartment requires an exterior staircase to enter, , may not be suitable for elderlybr- NOTE: There are other bookable vacation rentals on-site; other travelers may be present during your stay
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(6)

$334.38

/ Nightly
Private Vacation Home

Lakefront Maine House ~ 4 Mi to Colby College

Oakland, Maine, United States

With a stunning waterfront location on Messalonskee Lake, this old farmhouse vacation rental makes it hard to believe Colby College is only 4 miles away! The 4-bed, 1.5-bath house is primely situated for you to enjoy both, and it also boasts the essentials, like a full kitchen, free WiFi, and an air-conditioned interior. Launch a kayak into the water from the on-site dock during the day, then return to land in the evening and watch the sunset from the shared deck.brbr-- THE PROPERTY --brbrShared Deck | Lakefront View | Smart TVbrbrBedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: 3 Twin Beds | Bedroom 4: Queen Bed | Additional Sleeping: Pack 'n PlaybrbrSHARED AMENITIES (first-come, first-served): Dock, boat launch, Messalonskee Lake access, yard, 1 kayak/life vests (upon request)brMAIN FEATURES: Propane stove, dining table, window A/C unit, board gamesbrKITCHEN: Dishwasher, Keurig K-Duo coffee maker, toaster, toaster oven, slow cooker, fridge, stove & oven, microwave, dishware/flatware, trash bags/paper towels, cooking basicsbrGENERAL: Free WiFi, central heat, A/C unit, towels/linens, complimentary toiletries, iron/board/hair dryer (upon request)brFAQ: No fence before lake, quiet hours (10:00 PM-8:00 AM), top bunk not availablebrACCESSIBILITY: 2-story apartment, 4 steps to enterbrPARKING: Shared driveway (6 vehicles)brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, each with a separate nightly rate. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrMESSALONSKEE LAKE (on-site): Swimming, paddleboarding, kayaking, boating, fishingbrOUTDOOR REC: Quarry Road Trails (7 miles), French Mountain (14 miles), Titcomb Mountain (31 miles), Androscoggin Riverlands State Park (42 miles)brTHINGS TO DO: Colby College (4 miles), Thomas College (5 miles), Colby College Museum of Art (5 miles), Maine State Museum (18 miles), DEW Haven | Maine Zoo & Rescue (21 miles)brAIRPORT: Portland International Jetport (75 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- NOTE: The hair dryer, iron board, kayak, and iron available upon requestbr- NOTE: While using the kayak, local restrictions require a life jacket to be worn at all times. 1 adult and 1 child size life jacket is providedbr- NOTE: The property may not be suitable for children due to the unfenced lake and the property's sloped terrain; adult supervision is recommendedbr- NOTE: This 2-story apartment requires 4 steps to enterbr- NOTE: The top bunk in Bedroom 3 is not available for guest use and may not be used. It is not included in the home’s maximum occupancybr- NOTE: There are other bookable vacation rentals on-site; other travelers may be present during your staybr- NOTE: Please observe quiet hours from 10:00 PM to 8:00 AM
Bed 4

Bed

Bath 1

Bath

Sleep 9

Sleeps

Slider Thumb
Exceptional(6)

$142.81

/ Nightly
Apartment

Lakefront Oakland Vacation Rental w/ Dock + Views!

Oakland, Maine, United States

If you've been looking up and down Messalonskee Lake for a place to stay, this Oakland, Maine, vacation rental should be at the top of your list! The 1-bed, 1-bath apartment boasts a lakefront location a mere 4 miles from Colby College, plus all the basics a couple or solo traveler could need. Easy mealtimes are right around the corner in the kitchen, while the shared dock makes it easy to paddle, swim, or fish. In the evening, an air-conditioned interior awaits you after sunny days outside.brbr-- THE PROPERTY --brbrFree WiFi | Shared Deck | Self Check-InbrbrBedroom: Queen Bed | Additional Sleeping: Queen Air Mattress (Upon Request)brbrSHARED AMENITIES (first-come, first-served): Dock, boat launch, Messalonskee Lake access, yard, 1 kayak (upon request)brMAIN FEATURES: Flat-screen TV, dining table, lakefront viewbrKITCHEN: Toaster, fridge, stove & oven, microwave, dishware/flatware, trash bags/paper towels, cooking basicsbrGENERAL: Central heat, window A/C unit, towels/linens, complimentary toiletries, iron & board, hair dryerbrFAQ: No fence before lake, quiet hours (10:00 PM-8:00 AM)brACCESSIBILITY: 2-story apartment, interior staircase to access upper level bedroombrPARKING: Shared driveway (1 vehicle)brADDT’L ACCOMMODATIONS: Two additional properties are available on-site, each with a separate nightly rate. If you would like to reserve multiple rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbrMESSALONSKEE LAKE (on-site): Swimming, paddleboarding, kayaking, boating, fishingbrOUTDOOR REC: Quarry Road Trails (7 miles), French Mountain (14 miles), Titcomb Mountain (31 miles), Androscoggin Riverlands State Park (42 miles)brTHINGS TO DO: Colby College (4 miles), Thomas College (5 miles), Colby College Museum of Art (5 miles), Maine State Museum (18 miles), DEW Haven | Maine Zoo & Rescue (21 miles)brAIRPORT: Portland International Jetport (75 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowed br- No events, parties, or large gatherings br- Additional fees and taxes may apply br- Photo ID may be required upon check-inbr- NOTE: The hair dryer, iron board, iron, and kayak are available upon requestbr- NOTE: The property may not be suitable for children due to the unfenced lake and the property's sloped terrain; adult supervision is recommendedbr- NOTE: This 2-story apartment requires an interior staircase to access the bedroom on the upper levelbr- NOTE: There are other bookable vacation rentals on-site; other travelers may be present during your staybr- NOTE: Please observe quiet hours between 10:00 PM-8:00 AMbr- NOTE: While using the kayak, local restrictions require a life jacket to be worn at all times. One adult and one child-size life jacket is available for use
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(5)

$113.18

/ Nightly
Cottage

Lavender Haze Cottage in the Woods

Oakland, Maine, United States

Wind down our private road on the west side of prestigious Messalonskee Lake. Nestled in the heart of the Belgrade Lakes Region, historic Oakland has all of what Central Maine has to offer. Venture into the woods and enjoy your quaint and tranquil stay with us!brbrThis is a tiny house and is approximately a 300 sq foot space with ceiling heights of 6’4”. There is a small deck attached to the Main entrance with a canopy for covered seating. You will enter into the main space of the kitchen with a table, futon and TV. Then walk through to a private bathroom and then the main bedroom with a full size bed.brThe tiny house is set up as a 1 bedroom tailored to a single person or a couple. However, the futon can fold down to a bed and there is enough room for a small pack n play in the kitchen area. brThere is running water, hot water, electric/internet and a propane stove.brbrThe TV Has a roku stick with the ability to log into apps such as Hulu, Netflix, Disney +, etc. brbrThe washing machine is available for use for small washes. Please do not overfill the washer. It can only be filled ¾ of the tub. There is no dryer but a drying rack is available for use. There is laundry detergent under the sink. The washing machine will need to be plugged in to use it. Please limit to one use per stay and let us know as we will need to drain the holding tank. brbrPropane:brLocated outside the door on the porch there is 2 propane tanks. Only 1 needs to be turned on. Remove the black lid, then turn the dial to the on position. Propane tanks need to be turned on to use the stovetop and hot water. Please turn the tanks off when not in use.brbrHeat pump instructions:brThe heat pump is electric and can be controlled using the remote. There is a heat and air conditioner option. You are able to adjust the temperature yourself to desired temperature.brbrThe water is safe to use for cooking and a brita water filter is provided in tbe fridge for drinking. However we do recommend purchasing additional water for drinking.brbrThe toilet is an RV style toilet. To fill the toilet with water lightly press on the pedal, you will need to do this prior to pooping. brbrIf you have any trouble please let us know and we can stop by or walk you through it. brbrThe door is a little stubborn to lock. To lock the door, put the key as you would to lock a door. Once locked pull on the handle (as if you are pulling on it to open the door as you turn the key to pull it out). brbrAll trash can go in the garbage can in front of the porch.brbrIf you decide to go for a walk, please be respectful of our neighbors properties. There is no public access to the lake on the road, any lake frontage is private property.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(50)

$313.38

/ Nightly
Private Vacation Home

Classy AF Home Steps from Colby and Trails

Oakland, Maine, United States

THE BOOKING CALENDAR OPENS ONE YEAR IN ADVANCE, INCLUDING GRADUATION WEEKEND. Pet fees are 50$ PER animal. Lovingly renovated three bedroom home across the street from Colby College’s Senior Drive and Campus Trails. My husband’s grandfather built our house in the 40’s, we have done all of the renovations ourselves to create open, inviting spaces with unique touches while maintaining the original footprint. brbrFrom original hardwood floors, handmade glass tiles and knobs throughout the house to a custom built bathroom with radiant floor heating and a luxurious shower, our home is a labor of love.brbrKitchen: new refrigerator, dishwasher and gas stove, granite countertops, garbage disposal, breakfast bar, USB outlets, handmade cabinetry, and custom backsplash all provide an enjoyable workspace to entertain. Recycling and Returnable bins are available and labeled. We don’t own a microwave. Feel free to use anything that is around.brbrDining/Living Room: we removed a wall (the footprint remains with different types of flooring) and love the open floor plan it provides. The TV can turn it on the wall mount to keep you company anywhere downstairs. Please read French door instructions if you use them, they use a different locking system. brbrBedrooms: our home offers three bedrooms. The master looks out on the front yard with a queen bed and 32”smart tv. The second features a back yard view and a king bed. “The kid’s room” has a back yard view and a queen futon. brbrBathroom: Radiant floor heating, custom shower, and a Bluetooth speaker for shower singing will give your day a boost. brbrSunroom/Entryway: this area is a work in progress, we use it for a lot of things depending on the time of year but it functions as a mud room year round. brbrHall closet: we know it’s weird right now, it’s a work in progress. The toilet is totally functional and provides a .25 bath downstairs if you’d like to use it. brbrBasement: the washer/dryer are located downstairs. We also use this space for personal storage, but laundry facilities are accessible. brbrOutside: feel free to enjoy our large yard with family/friends. We love to garden and when the time is right, our beds provide a delicious, fresh summer meal. The garden is automatically watered in the morning and evening. Please harvest only what you will use and don’t forget all the herbs on the side of the garage! We prefer any flowers be left alone, please don’t cut them. brbrOur home uses well water that runs through a filter and a softener.
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Oakland