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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 20 Rentals in Oakland
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    NEW! 3BR Oakland Cottage 100 feet from The Water!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
    (5)Excellent
    Madison
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Loon Call1 / 26
    (1)Excellent
    Belgrade
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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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 14 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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    Location Information
    04352, Mount Vernon, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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
    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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    04364, East Winthrop, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Winslow
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Washer
    • Waterfront
    • Balcony
    • Housekeeping Included
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A great place to relax with family for a weekend getaway, or maybe a week or month's vacation! Quiet lakefront retreat would be great to clear writer's block or come photograph the loons, osprey, and bald eagles! Spectacular, one-of-a-kind waterfront log home set right on the water with 200 ft on...
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    04355, Winslow, Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    04345, Manchester, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Maple Hill Farm Inn1 / 46
    (1)Excellent
    Hallowell
    8 Bedrooms, 8 Bathrooms, Sleeps 19 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Sauna
    • Internet Access
    • DVD Player
    • Patio
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2013
    My husband and I spend 4 nights at this beautifully located, tranquil and inviting Bed and Breakfast. We very much enjoyed the very sincere hospitality and personal attitude of...
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    About this property
    In the Augusta area, Maple Hill Farm is in nearby Hallowell just 4 miles from I-95 Augusta Exit 109 on acres of country serenity. Maine's 1st certified “Environmental Leader” green lodging boasts the unique combination of many of the amenities of a quality hotel with the comfort of a quiet country...
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    04347, Hallowell, Maine
    Private Room - 8 Bedrooms, 8 Bathrooms, Sleeps 19
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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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    04917, Belgrade, Maine
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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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 11 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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    Location Information
    04352, Mount Vernon, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    04911, Anson, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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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    04901, Waterville, Maine
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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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
    04978, Smithfield, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Belgrade
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Private Garden
    • Waterfront
    • DVD Player
    • Terrace
    • Parking
    • Grill
    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
    04330, Belgrade, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    Location Information
    04917, Belgrade Lakes, Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hallowell
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    High end, downtown apartment that is steps away from several restaurants, shops and live music venues/pubs while still being in a quiet setting. Take advantage of the low price as we launch our new listing and provide us with feedback. We want this to be the perfect place to stay when you are in...
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    04347, Hallowell, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    NEW FOR 2017/2018! This south facing home at the water’s edge offers spectacular lakefront living, world class fishing right off your own dock, and both beautiful sunrises and sunsets. Cobbesseecontee Lake is ten miles of clean freshwater with excellent fishing and boating opportunities. This...
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    Location Information
    04364, East Winthrop, Maine
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Winslow
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Balcony
    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a separate apartment over the garage at our lake house. There is a living room/kitchen area with a pull out couch, a bedroom with two twin beds, a full bathroom, and a covered back deck/sitting area. There is a utility space with a washer and dryer on the first floor. Shared access to 523...
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    04901, Winslow, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Burnham
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • 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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    04922, Burnham, Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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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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    Location Information
    04901, Waterville, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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