A lake surrounded by trees with autumn leaves.

Holiday Homes in Oakland

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Oakland holiday homes

Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (14 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is €187
includes taxes & fees
11 Aug - 12 Aug
Discover Oakland charm near Colby College 10 min
Outdoor dining

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Oakland
10.0 out of 10, Exceptional, (14 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is €429
includes taxes & fees
10 Aug - 11 Aug
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Exterior

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.2 out of 10, Wonderful, (7 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is €160
includes taxes & fees
18 Aug - 19 Aug
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Exterior detail

Peaceful Home in Central Maine

Peaceful Home in Central Maine
Sidney
9.0 out of 10, Wonderful, (9 reviews)
"Had a great experience, host was super responsive and even accommodated us outside the parameters of their listing! House was super cute!! Highly recommend!!"
United States
Jessica G.
The price is €429
includes taxes & fees
9 Aug - 10 Aug
Peaceful Home in Central Maine
Exterior detail

Arden Cottage

Arden Cottage
Mount Vernon
The price is €390
includes taxes & fees
11 Aug - 12 Aug
Arden Cottage
Spa

Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is €231
includes taxes & fees
4 Aug - 5 Aug
Floating Island Dome - Pet-Friendly Lake Retreat
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.8 out of 10, Excellent, (23 reviews)
"Location is amazing "
United States
Laura Q.
The price is €338
includes taxes & fees
9 Aug - 10 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
Interior

A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (30 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
The price is €381
includes taxes & fees
21 Aug - 22 Aug
A soul soothing escape. Artistically built and lovingly maintained.
Exterior

Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is €390
includes taxes & fees
11 Aug - 12 Aug
Elizabeth Cottage
Exterior

Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is €390
includes taxes & fees
9 Aug - 10 Aug
Nightingale Cottage
TV

Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is €487
includes taxes & fees
9 Aug - 10 Aug
Once Upon a Time — A Peaceful Maine Escape
Private kitchen

Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (1 review)
"The host was very kind and always available for questions. The location was excellent. The property is stunning and my family had a wonderful time playing pool, basketball and other games."
United States
Michele M.
The price is €626
includes taxes & fees
23 Aug - 24 Aug
Welcome to "the east Madison chapel"
TV, books, offices

Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings

Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Wayne
10.0 out of 10, Exceptional, (1 review)
"The property was very nice!"
United States
James D.
The price is €1,017
includes taxes & fees
26 Aug - 27 Aug
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Dining

Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake

Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake
Strong
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful lake front home with awesome views. Very clean, cozy & spacious. Large fridge & dishwasher was a bonus. All the amenities supplied were great. Highly recommend staying here. Host was also great to deal with & replied very quickly when we had questions. Thanks for a wonderful stay. "
United Kingdom
TRISHA P.
Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake
WiFi, bed sheets

Newly renovated, New England 3-bedroom home in Skowhegan.

Newly renovated, New England 3-bedroom home in Skowhegan.
Skowhegan
The price is €154
includes taxes & fees
30 Jul - 31 Jul
Newly renovated, New England 3-bedroom home in Skowhegan.
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

Comfort Inn Augusta

Comfort Inn Augusta

10/10 Excellent
"The staff were wonderful. The property is great for a basic hotel."
Carrie 4-night trip
Posted less than an hour ago
Comfort Inn Augusta

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
139
Accommodation
159 Holiday Homes
Lowest Price
€160
Highest Price
€1,017