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Holiday Homes in Oakland

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    Don't let other travellers get your favourite Oakland area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Oakland
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    Oakland Cottage w/Deck - Right on McGrath Pond!1 / 24
    (1)Excellent
    Oakland
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    The following rentals are within 30 kilometres of Oakland.
    Wymans Willa1 / 22
    (6)Excellent
    Madison
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Loon Call1 / 26
    (2)Excellent
    Belgrade
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Gorgeous Lakefront Cottage on Cobbessee Lake near Lighthouse1 / 37
    (1)Excellent
    East Winthrop
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    We stayed at Keith's house in early June for an early season fishing trip. Aside for the weather, the trip was great. The house is as advertised and Keith was very quick to...
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    About this property
    Beautiful year around comfortable 2700 square foot lakefront home on Cobbossee Lake. Your family and friends will love this retreat on the shores of Cobbossee Lake! After watching a magnificent sunrise, enjoy lazy afternoons on the water with the help of a private dock, kayaks, a canoe, lakefront...
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    Location Information
    East Winthrop, Maine 04364
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Belgrade Lakes
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large Front enclosed screen porch with see thru roof. Also a rear enclosed screen porch. All knotted pine walls. Home is completely insulated. Large master bedroom with private bath, and Large TV on wall, with stove fire place. Hardwood floors, private office, closet and large windows to see...
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    Belgrade Lakes, Maine 04917
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakeside cottage w/dock,boat,gas fireplac,wash/dry1 / 18
    (14)Very good
    Mount Vernon
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Porch
    • Grill
    • Patio
    • Waterfront
    • DVD Player
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    My wife and I stayed at the cabin in mid October and it was incredibly relaxing and completely gorgeous. The weather was a bit chilly at night but we stayed nice and warm...
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    About this property
    Lake front ranch style cathedral ceiling cottage with two bedrooms,one with a queen bed and one with twin beds sleep 4.There is also a full pullout couch in the great room. Large great room with a propane stove with viewable flames, enclosed porch with jalousy windows,a bath with shower stall...
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    Mount Vernon, Maine 04352
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Belgrade Me lake front1 / 19
    (1)Excellent
    Mount Vernon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Grill
    • Balcony
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2016
    This is well kept vacation home on Long Pond in the Belgrade Lake Chain. Beautiful perinneal gardens, wild flowers along the 200 foot shore line facing west for great sunsets...
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    About this property
    West View for Beautiful sunsets off a 65 foot deck or water front deck. Enjoy covered hot tub, dock, float, perennial garden, recreational room with walk out cellar. Deck has sunsetter awning off an enclosed porch. Lake warms to 75-85 degrees. Washer & dryer; no linens, no smoking inside, no...
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    Mount Vernon, Maine 04352
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely remodeled, new floors, granite counter tops, tile bathrooms. Private yard. The space 1 Gingerbread Lane is the only House on the street. If you are Roman Catholic you can walk through the gate and across the parking lot to attend mass. Waterville hosts two colleges, a new YMCA, a...
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    Waterville, Maine 04901
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mount Vernon
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront relaxation with spectacular view of sunsets from the dock and the camp. All afternoon sun. 4 kayaks, a canoe, and a row boat. Sleep on the screened porch and listen to the loons! Quiet lake. Go for a walk on lovely private camp road. 2 miles from Apple Shed Bakery stocked with baked...
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    Mount Vernon, Maine 04352
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Winthrop
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a NEW OFFERING! This south facing home at water’s edge offers spectacular lakefront living, world class fishing right off the dock, and beautiful sunrises and sunsets. Many golf opportunities nearby, the closest being the Augusta Country Club, less than a mile away. Great for families. Just...
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    Location Information
    East Winthrop, Maine 04364
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Belgrade
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be one of the first families to stay in this spacious and comfy rustic Maine camp. It is furnished simply but comfortably. There is a deck with gas BBQ grill. Unlike most camps, the tap water comes from a well, not the lake. The home is situated as close to the water as new rules will allow,...
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    Belgrade, Maine 04917
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Belgrade
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Waterfront
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend a week or more at Star Point, and experience summer in Maine, the way life should be! Our comfortable cottage is situated at the wide end of Messalonskee Lake (aka Snow Pond), in the famous Belgrade Lakes chain. Located at the waters edge, our camp was built in 2004 and features an open floor...
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    Location Information
    Belgrade, Maine 04330
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Villa on Cobbossee Lake, private beach, lake view,1 / 20
    (1)Excellent
    Manchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxurious villa, sleeps 6 - 8, private beach, canoe, pool table, WiFi. If you are looking for an absolute quiet surrounding and beauty with unlimited privacy, this is the place. It is located on a point at the lake. The sandy beach is 100 feet from the house Private beach with 1500 feet of...
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    Location Information
    Manchester, Maine 04345
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Smithfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unfortunately no pets are allowed and smoking is only allowed outside up in the driveway area. There is also no fireworks of any kind allowed on the property, however in the summer there are public fireworks in the area. No weddings, family reunions, VISITORS or other gatherings exceeding the...
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    Location Information
    Smithfield, Maine 04978
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterville
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
    • Grill
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently Renovated with new kitchen. bathrooms, paint and floors. House currently being furnished (hence no pics of furniture). This lovely home will be completed for rentals April 1, 2018. 10 Country Way is envisioned to host and will be able to accommodate large parties. Set just minutes from...
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    Waterville, Maine 04901
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    Clean Cozy house awaiting for you in the woods no neigjbors or eand ? 125.00 p/n1 / 53
    (4)Excellent
    Anson
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Mountain Views
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2016
    Hi I stayed at this home last week attended the Skowhegan State Fair, used their Kayaks to go Kayaking on the Kennebec River where we seen American bald eagle! The house was...
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    About this property
    Clean Cozy and Bright 3 bedroom home all inclusive: house is in the woods the fishing spots are a short drive from the house. Some of the Best Fishing in the North East. Embden Lake in Embden Maine is just down the street from us. Kennebec River in Madison Maine, Clear Water Lake in Industry all...
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    Anson, Maine 04911
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Burnham
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the ultimate lakeside getaway at this wonderful Burnham vacation rental house. Nestled on the shores of Lake Winnecook, otherwise known as Unity Pond, this peaceful abode is perfect for travelers looking to experience the best of Maine! You'll feel right at home at this rustically charming...
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    Location Information
    Burnham, Maine 04922
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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