A lake surrounded by trees with autumn leaves.

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Oakland vacation homes

Exterior

1. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (15 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is AED 371
AED 781 total
includes taxes & fees
13 Aug - 14 Aug
Discover Oakland charm near Colby College 10 min
Outdoor dining

2. 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 AED 868
AED 1,717 total
includes taxes & fees
12 Aug - 13 Aug
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Exterior

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 AED 446
AED 567 total
includes taxes & fees
23 Aug - 24 Aug
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Exterior detail

4. Arden Cottage

Arden Cottage
Mount Vernon
The price is AED 771
AED 1,591 total
includes taxes & fees
11 Aug - 12 Aug
Arden Cottage
Exterior detail

5. 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 AED 1,170
AED 1,680 total
includes taxes & fees
23 Aug - 24 Aug
Peaceful Home in Central Maine
Terrace/patio

6. 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)
"We enjoyed our stay."
United States
Tyson W.
The price is AED 2,020
AED 4,644 total
includes taxes & fees
4 Sep - 5 Sep
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Property grounds

7. 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, (26 reviews)
"Location is amazing "
United States
Laura Q.
The price is AED 661
AED 1,397 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Cottage on water's edge of Lake Cobbosseecontee
Spa

8. Floating Island Dome - Pet-Friendly Lake Retreat

Floating Island Dome - Pet-Friendly Lake Retreat
Monmouth
The price is AED 432
AED 987 total
includes taxes & fees
23 Aug - 24 Aug
Floating Island Dome - Pet-Friendly Lake Retreat
Interior

9. 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 AED 909
AED 1,515 total
includes taxes & fees
21 Aug - 22 Aug
A soul soothing escape. Artistically built and lovingly maintained.
Exterior

10. Elizabeth Cottage

Elizabeth Cottage
Mount Vernon
The price is AED 771
AED 1,591 total
includes taxes & fees
11 Aug - 12 Aug
Elizabeth Cottage
Terrace/patio

11. 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, (2 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.
China Lake, Dog Friendly, Lots of space for family gatherings
Exterior

12. Nightingale Cottage

Nightingale Cottage
Mount Vernon
6.0 out of 10, (1 review)
The price is AED 771
AED 1,595 total
includes taxes & fees
10 Aug - 11 Aug
Nightingale Cottage
TV

13. Once Upon a Time — A Peaceful Maine Escape

Once Upon a Time — A Peaceful Maine Escape
Freedom
The price is AED 1,150
AED 1,979 total
includes taxes & fees
10 Aug - 11 Aug
Once Upon a Time — A Peaceful Maine Escape
Exterior

14. 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 AED 1,194
AED 3,315 total
includes taxes & fees
1 Sep - 2 Sep
July 7 to 14 Available: Big Porches w/ Scenic Views, Kayaks & Room to Gather
Private kitchen

15. 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 AED 1,469
AED 2,630 total
includes taxes & fees
10 Aug - 11 Aug
Welcome to "the east Madison chapel"
Dining

16. 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)
"Pet friendly with a nice spot on the lake. Nice place with great views."
United States
Al Q.
The price is AED 1,238
AED 1,631 total
includes taxes & fees
10 Aug - 11 Aug
Lakefront Home w/ Dock & Sugarloaf Access on Scenic Porter Lake
TV, books, offices

17. 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 AED 1,770
AED 4,148 total
includes taxes & fees
9 Sep - 10 Sep
Spacious Waterfront Log Home on Huge Lake in Private Cove: Host Weddings
Dining

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

Newly renovated, New England 3-bedroom home in Skowhegan.
Skowhegan
The price is AED 493
AED 677 total
includes taxes & fees
8 Sep - 9 Sep
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

Senator Inn & Spa

Senator Inn & Spa

10/10 Excellent
"Upgraded and best stay ever while visiting family."
Laura 2-night trip
Posted 2 hours ago
Senator Inn & Spa