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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Oakland

Fridge, oven, stovetop, dishwasher
Classy AF Home Steps from Colby and Trails

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (49)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails
Front of property
My Valhalla Farm

My Valhalla Farm

3.5 star property
Oakland
The price is ￥35,048
￥53,780 total
includes taxes & fees
Dec 5 - Dec 6
My Valhalla Farm
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is ￥18,703
￥35,430 total
includes taxes & fees
Dec 8 - Dec 9
Sister A-Frame in Woods B
Property grounds
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2.0 star property
Oakland
10.0 out of 10, Exceptional, (4)
"We had an excellent stay on the lake. The property is beautiful and the house has everything, with great views from all 3 levels. We would love to stay again! "
United States
Ashley L.
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Property grounds
Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.

Oakland
10.0 out of 10, Exceptional, (43)
"The place was clean, very spacious and comfortable. Having the laundry was helpful, so I didn’t have to worry about doing laundry when I got home late (also, I spilled coffee on the way there, so I’m glad the stain was gone)."
United States
Keeko
The price is ￥16,356
￥38,373 total
includes taxes & fees
Dec 5 - Dec 6
Central Maine Apartment offering 4 Seasons of Fun.
Interior
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland
9.2 out of 10, Wonderful, (26)
"Adorable cabin well stocked with plenty of space. Beautiful view! Nice and Clean. Needed help with the door lock and they were quick to respond and help. "
United States
Angela
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Fridge, microwave, stovetop, coffee/tea maker
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.

Oakland
The price is ￥24,253
￥48,678 total
includes taxes & fees
Dec 5 - Dec 6
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
TV
Spacious Country Home w/ Hot Tub, near Colby/Thomas

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

Sidney
9.8 out of 10, Exceptional, (35)
"Very nice hot tub, quite and beautiful area! Air quality amazing and AC works fantasticly!"
United States
Nathan
The price is ￥36,139
￥76,237 total
includes taxes & fees
Dec 28 - Dec 29
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Property grounds
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
Readfield
10.0 out of 10, Exceptional, (7)
"It was a wonderful week. The cabin is very well appointed. We lacked for nothing! Thank you "
United States
Gigi A.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
Exterior
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

Strong
9.4 out of 10, Exceptional, (137)
"Very relaxing!"
United States
Bradford B.
The price is ￥13,957
￥18,594 total
includes taxes & fees
Dec 5 - Dec 6
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Property grounds
Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester
8.6 out of 10, Excellent, (18)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
The price is ￥20,238
￥49,444 total
includes taxes & fees
Dec 6 - Dec 7
Cozy Cottage on water's edge of Lake Cobbosseecontee
Fridge, microwave, oven, stovetop
Large Secluded Cabin on the Lake - Now booking 2+ night stays

Large Secluded Cabin on the Lake - Now booking 2+ night stays

Smithfield
10.0 out of 10, Exceptional, (66)
"Great vacation with 3 generations of our family. House was beautiful, lake clean with great swimming and fishing. Hope to return for years to come. "
United States
David M.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Outdoor spa tub
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Manchester
10.0 out of 10, Exceptional, (255)
"We had a fantastic time! The lake is beautiful and the house has everything you need to enjoy it. "
United States
Dave S.
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly
Fridge, microwave, oven, stovetop
Lakefront Cabin

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"Very clean, great view, quiet, serene location right on the lake."
United States
katherine b.
Lakefront Cabin
Property grounds
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
9.8 out of 10, Exceptional, (86)
"Absolutely amazing property, everything we were looking for and an amazing host too! Highly recommend! "
United States
samantha c.
Private and Calming Waterfront to the Rescue!
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Whitefield
9.8 out of 10, Exceptional, (30)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
The price is ￥23,262
￥34,822 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Terrace/patio
The Cabin Skowhegan

The Cabin Skowhegan

Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is ￥15,508
￥32,624 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Cabin Skowhegan
Dining
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Albion
9.8 out of 10, Exceptional, (37)
"Nice place, great fishing. "
United States
Bryan W.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Interior
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This house was absolutely stunning! Had absolutely everything that you needed the house offered everything that one would need and plenty of space for everybody! The game room was so fun! The hot tub was a great bonus! Everyone had an amazing time while staying."
United States
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
Interior
Lakefront, Stunning Home only 30 min to Sugarloaf!

Lakefront, Stunning Home only 30 min to Sugarloaf!

Strong
10.0 out of 10, Exceptional, (37)
"Jeff and Jess’ lakefront home made for a perfect retreat to relax and take in the peace of the lake and loons. Comfortable bed, nice and clean with everything you need to enjoy yourself. Great communication with the owners throughout the process. Hard to pack our bags and say goodbye. Looking forward to returning."
United States
Brian B.
Lakefront, Stunning Home only 30 min to Sugarloaf!
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"This hotel is amazing! From the friendly staff to the clean rooms it was a great experience. The restaurant was excellent as well. I was traveling on business and I will definitely return."
Kathleen 1-night trip
Posted 3 days ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, there are vacation rentals close to popular sights in Oakland, or you can go with a secluded option if you want a relaxing place to stay. Oakland is known for its shopping and restaurants. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals in Oakland?

Classy AF Home Steps from Colby and Trails: This Oakland vacation home rental offers a private yard, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Our travelers also rate Cozy Long Pond Cottage: private mooring & shared dock as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 29 Expedia vacation rentals in Oakland for a memorable vacation.

What can I see and do in Oakland?

Explore the area and family-friendly sights such as Maine State Museum, or get out into nature at a spot like Belgrade Lakes Chain. Colby College and Tree Spirits are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakland?

Vacation rentals are private accommodations you can stay in for several days or more in Oakland. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family gatherings.