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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 139 Vacation Homes in Oakland with updated reviews, rates, and availability.

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Fridge, microwave, oven, dishwasher

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Property grounds

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2.0 star property
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Outdoor spa tub

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly

10.0 out of 10, Exceptional, (240)
"Had another great fishing trip with this as our home base! Always clean and comfortable! "
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
The Modern Maine Retreat
Outdoor dining

The Modern Maine Retreat

10.0 out of 10, Exceptional, (3)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
Brand New Waterfront Lake House (completed July 2021)
Miscellaneous

Brand New Waterfront Lake House (completed July 2021)

10.0 out of 10, Exceptional, (22)
"We had an amazing week at this property. House was spacious, clean and had everything that we needed. We plan to stay here again next summer! "
Brand New Waterfront Lake House (completed July 2021)
Cozy House in the heart of Waterville Maine.
TV

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (38)
"Everything was good. Would stay there again."
Cozy House in the heart of Waterville Maine.
Veedon Fleece on the Lake
Miscellaneous

Veedon Fleece on the Lake

10.0 out of 10, Exceptional, (15)
"We enjoyed the house tremendously "
Veedon Fleece on the Lake
Great Pond Waterfront: Dog-friendly Home Near Colby College
Beach towels

Great Pond Waterfront: Dog-friendly Home Near Colby College

9.6 out of 10, Exceptional, (30)
"This was our third year in a row spending most of August at the wonderful Loons nest! Brent and Sarah are great and responsive hosts. The views and water are incomparable and the cabin itself has all of the modern conveniences while maintaining a rustic charm. It is one of our favorite places in the world and hope to be back next year!"
Great Pond Waterfront: Dog-friendly Home Near Colby College
Spectacular Location Reasonably Priced
Exterior

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (29)
"This is the quintessential cabin rental which provides good modern facilities with the vintage Maine camp feel we have always looked for. We will return to our 3rd rental at this property next year. Very satisfied with our experience."
Spectacular Location Reasonably Priced
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

8.2 out of 10, Very Good, (16)
"Great location! Very nice place"
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior

Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.

10.0 out of 10, Exceptional, (56)
"Super cozy place. Use a silver popper on the pond"
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Cozy Long Pond Cottage: private mooring & shared dock
Miscellaneous

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
" Cute place"
Cozy Long Pond Cottage: private mooring & shared dock
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (77)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!
Lakefront, Stunning Home only 30 min to Sugarloaf!
Miscellaneous

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (28)
"Great property, exceptional views....the house has great access to the lake. It snowed during our trip, so the large front windows made it a great vantage point to watch the snow and our ice fishing traps. "
Lakefront, Stunning Home only 30 min to Sugarloaf!
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Terrace/patio

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (5)
"Did not want to leave. So thankful work took me to this beautiful property. The views did not disappoint. Alyssa and Mike were such a pleasure to work with. Thank you for opening your home away from home for me. My family and I will definitely be back. "
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Property grounds

Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME

10.0 out of 10, Exceptional, (16)
"We were a group of 6 men on our annual fishing trip. The rental did not disappoint, Owners were very attentive to our needs leading up to our visit. Home was well appointed, clean and came as advertised. Great Lake for fishing, caught trout, bass, cusk and perch. The eagle that hung around while we fished was an added bonus. Overall a great trip!!!"
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Find Your Bliss at this Private and Captivating Lakeside Retreat
Smart TV, video games, foosball, table tennis

Find Your Bliss at this Private and Captivating Lakeside Retreat

10.0 out of 10, Exceptional, (20)
"We decided to book this beautiful property to bring our family together for a long weekend to celebrate Thanksgiving together for our first holiday since the passing of our father. This was the perfect spot! The house accommodated all 12 of us easily with plenty of space for more! The hope décor is perfection and the views are priceless! The days we spent there with filled with tears and laughter and reliving fond memories while making new memories. Dan was absolutely wonderful to deal with...
Find Your Bliss at this Private and Captivating Lakeside Retreat
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Fridge, microwave, oven, stovetop

Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH

10.0 out of 10, Exceptional, (29)
"Great accommodations from Chip and Kathy. In addition, they live nearby which is great in case anything pops up. Wood stove was already on when we arrived which was warm and cozy. House is right off of Rt 27 with about a 30 minute ride to the Sugarloaf base lodge. Will definitely stay there again."
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Every window has a spectacular lake view Low fees
Miscellaneous

Every window has a spectacular lake view Low fees

10.0 out of 10, Exceptional, (33)
"My fiance and I visited this property with a few friends to celebrate his birthday with a fun-filled ice fishing weekend. Tina was a fantastic host who communicated with us promply and clearly and gave us all the information we needed to settle in and feel at home in her charming lakeside cottage. She was quick to reply to any of our questions and seemed genuinely pleased to have us there. The rental itself was homey and clean, with plenty of room for everyone. Although the lake accessible from...
Every window has a spectacular lake view Low fees
Lake House Wooded Vacation Retreat and Nature Escape

Lake House Wooded Vacation Retreat and Nature Escape

9.8 out of 10, Exceptional, (49)
"My friends and I stayed here for a long weekend at sugarloaf, although a little far we had a blast!"
Lake House Wooded Vacation Retreat and Nature Escape
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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Other property types in Oakland

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Beach towels

Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College

9.6 out of 10, Exceptional, (10)
"We spent a beautiful fall weekend at Cedar Estates, the house was clean and very well equipped, as described in the listing. We enjoyed a nice campfire on Saturday night at the fire pit. Our 2 dogs really enjoyed exploring and running outside as well! Clean sheets and towels, hot water - lovely overall!"
Belgrade Lakes Cottage w/ Long Pond beach access close to Augusta, Colby College
Cozy Long Pond Cottage: private mooring & shared dock
Miscellaneous

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (13)
" Cute place"
Cozy Long Pond Cottage: private mooring & shared dock
The Modern Maine Retreat
Outdoor dining

The Modern Maine Retreat

10.0 out of 10, Exceptional, (3)
"Worked out perfectly for our needs. Owner responded immediately to assist us with minor issue. We would, and most likely will, rent this home again. Location was great for our purpose. Plenty of room."
The Modern Maine Retreat
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.