A lake surrounded by trees with autumn leaves.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Oakland vacation 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, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is ￥33,344
￥68,642 total
includes taxes & fees
Sep 4 - Sep 5
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
A single-story house with a gray siding exterior, a white front door, and two flower planters on either side of the entrance.

2. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is ￥25,294
￥45,224 total
includes taxes & fees
Sep 17 - Sep 18
Discover Oakland charm near Colby College 10 min
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, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is ￥18,291
￥23,399 total
includes taxes & fees
Sep 10 - Sep 11
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A house with a white front door, a wreath, and flower boxes on the windowsills.

4. Arden Cottage

Arden Cottage
Mount Vernon
The price is ￥33,644
￥69,241 total
includes taxes & fees
Sep 6 - Sep 7
Arden Cottage
A covered patio with a view of a lake, outdoor furniture, and a wooden deck.

5. Family's Paradise: 3BR/2BA,Game Room & Lake Access

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
10.0 out of 10, Exceptional, (11 reviews)
"This property is so special! The setting is absolutely gorgeous and the home itself is perfect both inside and out. We stayed here for a college graduation and had multiple generations-the layout was terrific for all of us. We especially loved sitting by the lake, enjoying the views from the screened in porch, and family time in the game room. The communication from the host was excellent and the entire process from beginning to end was seamless. We hope to return for another stay!"
United States
Jennifer E.
The price is ￥48,704
￥153,499 total
includes taxes & fees
Sep 21 - Sep 22
Family's Paradise: 3BR/2BA,Game Room & Lake Access
A room with a hexagonal glass ceiling, a bed with a plaid blanket, and a view of greenery outside.

6. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is ￥11,663
￥34,192 total
includes taxes & fees
Sep 27 - Sep 28
Floating Island Dome - Pet-Friendly Lake Retreat
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

7. 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.
A soul soothing escape. Artistically built and lovingly maintained.
A cozy living room with a sofa, armchairs, a coffee table, and a large window with a view of a boat.

8. Amazing Lake House On Great Pond! Stunning Sunsets & Renovated Bunkhouse Bar

Amazing Lake House On Great Pond! Stunning Sunsets & Renovated Bunkhouse Bar
Belgrade
The price is ￥55,573
￥69,228 total
includes taxes & fees
Sep 17 - Sep 18
Amazing Lake House On Great Pond! Stunning Sunsets & Renovated Bunkhouse Bar
A wooden cabin interior with a sofa, dining table, and a chair with a woven seat.

9. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is ￥38,584
￥71,825 total
includes taxes & fees
Sep 14 - Sep 15
Once Upon a Time — A Peaceful Maine Escape
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

10. 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, (3 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 ￥66,878
￥127,761 total
includes taxes & fees
Sep 8 - Sep 9
China Lake, Dog Friendly, Lots of space for family gatherings
A large, two-story house with a well-lit front porch and multiple windows.

11. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is ￥33,644
￥69,241 total
includes taxes & fees
Sep 6 - Sep 7
Elizabeth Cottage
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 ￥52,068
￥144,418 total
includes taxes & fees
Sep 10 - Sep 11
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 ￥33,644
￥70,289 total
includes taxes & fees
Sep 13 - Sep 14
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, (2 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 ￥63,512
￥113,707 total
includes taxes & fees
Sep 4 - Sep 5
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
10.0 out of 10, Exceptional, (1 review)
"The property was very nice!"
United States
James D.
The price is ￥72,493
￥174,379 total
includes taxes & fees
Sep 9 - Sep 10
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

The Skowhegan By Kasa

The Skowhegan By Kasa

8/10 Good
"Great place - would get another star if restaurant or snack bar was open for breakfast"
Andrea 1-night trip
Posted 8 hours ago
The Skowhegan By Kasa

Find out more about Oakland

Oakland Vacation Homes information

Number of reviews
7,674
Accommodation
158 Vacation Homes
Lowest Price
￥18,172
Highest Price
￥43,354