Photo by Marc Maheu

Holiday Homes in Oakland

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Featured Holiday Homes in Oakland and around

Exterior
Charming historic guest house on farm 3 bedrooms wood stove pet friendly
Charming historic guest house on farm 3 bedrooms wood stove pet friendly
10.0 out of 10, Exceptional, (7)
"Enjoyed a 2 night stay at this quiet country retreat. Our host was friendly and took time to visit. The kitchen was well stocked and it's a charming historic structure, equipped with modern conveniences. What more could you want! "
The price is €317
includes taxes & fees
27 Oct - 28 Oct
Charming historic guest house on farm 3 bedrooms wood stove pet friendly
Fridge, microwave, oven, stovetop
Discover Oakland charm near Colby College 10 min
Discover Oakland charm near Colby College 10 min
2.0 star property
10.0 out of 10, Exceptional, (4)
"New, clean and had everything we needed. "
The price is €232
includes taxes & fees
15 Oct - 16 Oct
Discover Oakland charm near Colby College 10 min
Front of property
My Valhalla Farm
My Valhalla Farm
3.5 star property
The price is €352
includes taxes & fees
26 Oct - 27 Oct
My Valhalla Farm
Exterior detail
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
10.0 out of 10, Exceptional, (3)
"Excellent service and perfect for our stay. Would book again!"
The price is €135
includes taxes & fees
27 Oct - 28 Oct
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee
Cozy Cottage on water's edge of Lake Cobbosseecontee
8.8 out of 10, Excellent, (16)
"Perfect old fashion Maine cottage! Great sunsets!"
The price is €282
includes taxes & fees
26 Oct - 27 Oct
Cozy Cottage on water's edge of Lake Cobbosseecontee
Interior
Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly
Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly
10.0 out of 10, Exceptional, (3)
"Great spot on the lake! The house was super clean, beds were very comfortable, kitchen was well stocked and had everything we needed while we were there. The neighbor's house is really close to the property along the shared beach, and while it was never an issue for us, you may hear the neighbors as they come and go from their house. Overall a fantastic stay."
The price is €342
includes taxes & fees
15 Oct - 16 Oct
Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly
Property grounds
3350 Middle Road
3350 Middle Road
8.0 out of 10, Very good, (3)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
The price is €297
includes taxes & fees
27 Oct - 28 Oct
3350 Middle Road
Property grounds
Every window has a spectacular lake view Low fees
Every window has a spectacular lake view Low fees
9.8 out of 10, Exceptional, (43)
"Nice place. Plenty of space. Clean and all the amenities you could need "
The price is €406
includes taxes & fees
21 Oct - 22 Oct
Every window has a spectacular lake view Low fees
Interior
Lakefront, Stunning Home only 30 min to Sugarloaf!
Lakefront, Stunning Home only 30 min to Sugarloaf!
10.0 out of 10, Exceptional, (36)
"The house was very comfortable. Grass and lake well maintained. Plenty of towels and the whirlpool bath was very a nice bonus. Kayaks were fun. "
The price is €361
includes taxes & fees
15 Oct - 16 Oct
Lakefront, Stunning Home only 30 min to Sugarloaf!
Exterior
A soul soothing escape. Artistically built and lovingly maintained.
A soul soothing escape. Artistically built and lovingly maintained.
10.0 out of 10, Exceptional, (29)
"We loved the property. The Views are great and it is very comfortable and quiet. I would highly recommend staying here."
The price is €395
includes taxes & fees
14 Nov - 15 Nov
A soul soothing escape. Artistically built and lovingly maintained.
Terrace/patio
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
9.6 out of 10, Exceptional, (4)
"Wonderful stay! This is the third year in a row our group of "mature" fishermen have stayed at this lake. This was by far the best place we stayed at. Views and setting are all that we could ask for. We'll be back again."
The price is €598
includes taxes & fees
26 Oct - 27 Oct
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oakland Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
""No Pets" is a wonderful thing for a person with severe animal allergies. Thank goodness! Also, the hotel is clean, well-maintained, quiet, and comfortable. We will definitely stay here again!!"
Lisa 1-night trip
Posted 1 day ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
145
Accommodation
131 Holiday Homes
Lowest Price
€135
Highest Price
€598

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