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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 143 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
Private and Calming Waterfront to the Rescue!
Property grounds

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (77)
"clean place listed accordingly "
Private and Calming Waterfront to the Rescue!
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)
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Fridge, microwave, stovetop, dishwasher

Peaceful Fisherman's Paradise w/ Deck + Fire Pit!

10.0 out of 10, Exceptional, (26)
"The property was as advertised! For a family with little kids, this was a great place to stay. David was helpful and very responsive!"
Peaceful Fisherman's Paradise w/ Deck + Fire Pit!
Cozy House in the heart of Waterville Maine.
TV

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (39)
"Everything was good. Would stay there again."
Cozy House in the heart of Waterville Maine.
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
Property grounds

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
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
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Outdoor spa tub

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (19)
"We had an awesome time playing in the snow in the backyard and enjoying the relaxing hot tub. The house accommodated our large family and the host was very responsive and came quickly when we needed help. Will definitely come back "
Spacious Country Home w/ Hot Tub, near Colby/Thomas
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
Perfect Maine Getaway in a Recently Renovated Cabin!
Fridge, stovetop, dishwasher, coffee/tea maker

Perfect Maine Getaway in a Recently Renovated Cabin!

9.6 out of 10, Exceptional, (14)
"Had a great time at the cabin, just steps from town. Would recommend if you want to close to everything."
Perfect Maine Getaway in a Recently Renovated Cabin!
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
Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
Fridge, microwave, oven, stovetop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop

Spacious 5-bedroom lakefront home on pristine Lower Narrows Pond in Winthrop
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
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, (30)
"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
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

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
Cozy Long Pond Cottage: private mooring & shared dock
Property grounds

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
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
Miscellaneous

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (18)
"Absolutely beautiful house on the lake. Enjoyed this with my husband and cousins. Just as described. Responsive host."
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly
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.