A lake surrounded by trees with autumn leaves.

Search Holiday Homes in Oakland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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 £274
includes taxes & fees
31 Oct - 1 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)
"Less than 5 minutes to Colby. We were there for a camp. AC in both bedrooms. Nice artwork and decor."
United States
Leslie G.
The price is £196
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, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is £111
includes taxes & fees
19 Oct - 20 Oct
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 £330
includes taxes & fees
19 Oct - 20 Oct
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 £313
includes taxes & fees
19 Oct - 20 Oct
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)
"We will miss this house and would be happy to come back again. The ac in every bedroom plus the main floor made the most humid days comfortable. And China Lake is a wonderful place to have a piece of to yourself."
United States
Lisa J.
The price is £374
includes taxes & fees
20 Oct - 21 Oct
China Lake, Dog Friendly, Lots of space for family gatherings
A two-story house with a balcony, surrounded by trees and a grassy yard.

7. Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach

Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
Smithfield
10.0 out of 10, Exceptional, (4 reviews)
"Best vacation home ever!!! Host, property, and home met all of our families expections. Just perfect !"
United States
Dianne S.
Stunning Lakefront Retreat set on a Private point on North Pond, 9 acres w/beach
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

8. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is £300
includes taxes & fees
20 Oct - 21 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.

9. 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.
The price is £306
includes taxes & fees
8 Nov - 9 Nov
Salt water hot tub, king size beds, dog friendly, lake front, dock, boat launch
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 £330
includes taxes & fees
19 Oct - 20 Oct
Arden Cottage
A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a table and chairs.

11. Renovated Year-Round Lake Retreat on Annabessacook Lake

Renovated Year-Round Lake Retreat on Annabessacook Lake
Monmouth
The price is £252
includes taxes & fees
19 Oct - 20 Oct
Renovated Year-Round Lake Retreat on Annabessacook Lake
A two-story house with a red roof, located by a lake surrounded by dense green trees.

12. July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather

July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is £673
includes taxes & fees
26 Oct - 27 Oct
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
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 £330
includes taxes & fees
19 Oct - 20 Oct
Nightingale Cottage
A wooden kitchen with a large window, a black countertop, and three bar stools.

14. 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 £531
includes taxes & fees
19 Oct - 20 Oct
Welcome to "the east Madison chapel"
A spacious log cabin interior with a large living area, a stone fireplace, and a staircase leading to an upper level.

15. 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 £762
includes taxes & fees
20 Oct - 21 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"Great value for the money."
Robert 1-night trip
Posted 3 hours ago
Fireside Inn & Suites Waterville

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
147
Accommodation
154 Holiday Homes
Lowest Price
£111
Highest Price
£762