A lake surrounded by trees with autumn leaves.

Holiday Homes in Oakland

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Oakland holiday homes

A wooden deck with outdoor furniture, a large potted plant, and string lights.

1. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (18 reviews)
"We loved staying at the farm! My kids enjoyed meeting the horse and donkey on property. It was perfect for our family!"
United States
Shana S.
The price is €294
includes taxes & fees
1 Nov - 2 Nov
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

2. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is €233
includes taxes & fees
2 Nov - 3 Nov
Cozy House in the heart of Waterville Maine.
A modern building with a black exterior and a large glass entrance.

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (10 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is €133
includes taxes & fees
2 Nov - 3 Nov
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A large, two-story house with a well-lit front porch and multiple windows.

4. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is €395
includes taxes & fees
1 Nov - 2 Nov
Elizabeth Cottage
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

5. 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, (31 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 €358
includes taxes & fees
2 Nov - 3 Nov
A soul soothing escape. Artistically built and lovingly maintained.
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

6. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
The price is €577
includes taxes & fees
29 Oct - 30 Oct
China Lake, Dog Friendly, Lots of space for family gatherings
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

7. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is €340
includes taxes & fees
29 Oct - 30 Oct
Once Upon a Time — A Peaceful Maine Escape
A cozy living room with a sofa, ottoman, and dining table with chairs. There are windows with curtains, a wooden ceiling, and a view of the outdoors.

8. Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch

Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
Canaan
9.8 out of 10, Exceptional, (9 reviews)
"Awesome stay right on the water. "
United States
Timothy S.
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
A wooden porch with a door, steps, and potted plants.

9. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
The price is €313
includes taxes & fees
2 Nov - 3 Nov
Renovated Year-Round Lake Retreat on Annabessacook Lake
A house with a white front door, a wreath, and flower boxes on the windowsills.

10. Arden Cottage

Arden Cottage
Mount Vernon
The price is €395
includes taxes & fees
1 Nov - 2 Nov
Arden Cottage
A wooden kitchen with a large window, a black countertop, and three bar stools.

11. Welcome to "the east Madison chapel"

Welcome to "the east Madison chapel"
Madison
10.0 out of 10, Exceptional, (4 reviews)
"Great for kids. Lots of space. Convenient location. Plenty to do locally or venture out to explore. Recommend renting the golf cart to get back and forth down the camp road to the dock.. water is clear and clean, rock bottom at shore. Fast response from host who lives close by."
United States
Melissa B.
The price is €635
includes taxes & fees
2 Nov - 3 Nov
Welcome to "the east Madison chapel"
A campfire setup by a calm lake with a forest in the background.

12. Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees
Wayne
9.8 out of 10, Exceptional, (53 reviews)
"Great host!"
United States
Christine Z.
The price is €387
includes taxes & fees
9 Nov - 10 Nov
Every window has a spectacular lake view Low fees
A small, single-story house with a white exterior and a dark roof. It features a front door, two windows with shutters, and a small porch area.

13. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is €395
includes taxes & fees
1 Nov - 2 Nov
Nightingale Cottage
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

14. 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
9.0 out of 10, Wonderful, (2 reviews)
"The property was very nice!"
United States
James D.
The price is €913
includes taxes & fees
29 Oct - 30 Oct
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Plenty of parking"
Robert 5-night trip
Posted 5 hours ago
Fireside Inn & Suites Waterville

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
182
Accommodation
151 Holiday Homes
Lowest Price
€133
Highest Price
€913