We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Oakland Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $275 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Oakland area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Oakland
    Sort by:
    Default
    Oakland
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 30 kilometres of Oakland.
    Wymans Willa1 / 22
    (1)Excellent
    Madison
    3 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    East Winthrop
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Villa on Cobbossee Lake, private beach, lake view,1 / 20
    (1)Excellent
    Manchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Traveller-friendly cancellation policy
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Waterfront
    • Washer
    • 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...
    View all property information
    Location Information
    Manchester, Maine 04345
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Peaceful Lakefront Cottage on Beautiful Long Pond1 / 12
    (2)Excellent
    Mount Vernon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Satellite TV
    • DVD Player
    • Grill
    • Parking
    • Outdoor Dining Area
    • Waterfront
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy life in the Maine woods. Sit on the dock or deck and watch osprey and bald eagles fly overhead and loons and great blue heron catch fish. Enjoy a refreshing swim out to the float and lie in the sun. Canoe down the lake to numerous private coves and picnic spots. (There are five cottages...
    View all property information
    Location Information
    Mount Vernon, Maine 04352
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Belgrade
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new camp is something special. Constructed in the traditional Maine camp style, it has been wonderfully put together by local craftsmen and has beautiful, bright varnished pine interior v-match walls. For maximum privacy the home is situated approximately 200 ft from the lake, surrounded...
    View all property information
    Location Information
    Belgrade, Maine 04917
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Belgrade Me lake front1 / 19
    (1)Excellent
    Mount Vernon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Mount Vernon, Maine 04352
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Maple Hill Farm Inn1 / 46
    (1)Excellent
    Hallowell
    8 Bedrooms, 8 Bathrooms, Sleeps 19 Quick View
    Traveller-friendly cancellation policy
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Sauna
    • Internet Access
    • DVD Player
    • Patio
    • Mountain Views
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Hallowell, Maine 04347
    Private Room - 8 Bedrooms, 8 Bathrooms, Sleeps 19
    Make Enquiry
    Smithfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Wi-Fi
    • 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...
    View all property information
    Location Information
    Smithfield, Maine 04978
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    The Lake House On Great Pond1 / 10
    (3)Excellent
    Belgrade
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Waterfront
    • Satellite TV
    • Internet Access
    • Central Heating
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A unique 2 level, year round home on Great Pond. Situated on the eastern shore in Hatch Cove, the sunsets are incredible. The home is 40 feet from the waters edge with 110 ft of frontage. Children can enjoy the 14 ft wide sandy beach area for safe play. The open concept first level has...
    View all property information
    Location Information
    Belgrade, Maine 04917
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Lakeside cottage w/dock,boat,gas fireplac,wash/dry1 / 18
    (14)Very good
    Mount Vernon
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Traveller-friendly cancellation policy
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Mount Vernon, Maine 04352
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    PRIVATE Maine Lakefront Cottage, Private Boat Dock1 / 19
    (8)Very good
    Norridgewock
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Waterfront
    • Central Heating
    • Porch
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Now booking for Summer of 2017** Hinkley Cove Cottages, owned by Clyde & Mary Hinkley, are located in Hinkley Cove on the beautiful west shore of North Pond, Maine. Enjoy lazy days at the PRIVATE natural sand beach, go for a swim, catch some fish, a boat trip, enjoy your own PRIVATE boat dock,...
    View all property information
    Location Information
    Norridgewock, Maine 04957
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Secluded , Romantic Maine Cottage on Mountain Lake1 / 11
    (12)Excellent
    Augusta
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dramatically set on the side of a mountain, overlooking a sparkling clean, spring-fed 12-acre lake, our cottage is perfect for honeymooners or nature lovers-- or anyone who appreciates secluded peace and quiet. It features a high deck facing our 200 feet of natural lake frontage with dock and...
    View all property information
    Location Information
    Augusta, Maine 04330
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    Burnham
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Traveller-friendly cancellation policy
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Patio
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have the ultimate lakeside getaway by escaping to this wonderful Burnham vacation rental house. Nestled on the shores of Lake Winnecook, otherwise known as Unity Pond, with 2,528 acres of water recreation space, this peaceful abode is perfect for travelers looking to experience the best of Maine!...
    View all property information
    Location Information
    Burnham, Maine 04922
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    DUCK INN - WAYNE, MAINE | ON DEXTER POND | KAYAKING, FISHING, SWIMMING, BIRDING1 / 29
    (2)Excellent
    Wayne
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Terrace
    • Balcony
    • Wi-Fi
    • DVD Player
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2015
    My family and I had such a wonderful time at the Duck Inn. Words cannot adequately capture the tranquility of this beautiful house on a picturesque pond . The house itself was...
    Reviewed 3 September 2013
    This place was everything I wanted. My husband wanted to rent a "cabin" or "cottage" on a lake. He also likes to camp - I do not! This house was well...
    See all reviews
    About this property
    DUCK INN - Wayne Maine Saturday to Saturday full weeks in July and August. You can see more pictures on our Facebook page: https://www.************/DuckInnVacationRentalWayneMaine/ Listen to the Loons. Watch the lake smoke drift. Take in the colors of the sunrise. Breathe. Relax. Renew. De-stress....
    View all property information
    Location Information
    Wayne, Maine 04284
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Belgrade
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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,...
    View all property information
    Location Information
    Belgrade, Maine 04917
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    List your property
    Owner log in