Photo by Marc Maheu

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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 2 Resorts in Oakland with updated reviews, rates, and availability.

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
Property grounds

Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore

2.0 star property
10.0 out of 10, Exceptional, (6)
"Such a beautiful spot and house. It was perfect for our family of four and our dog. The hosts were gracious, left us gifts and it was fully stocked of everything you would need. We would definitely go back."
The price is AED 547
AED 1,025 total
includes taxes & fees
24 Mar - 25 Mar
Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore
Charming 3-bedroom Duplex Historic Farmhouse
Fridge, microwave, oven, stovetop

Charming 3-bedroom Duplex Historic Farmhouse

Charming 3-bedroom Duplex Historic Farmhouse
Pressey House Lakeside Bed & Breakfast
Exterior

Pressey House Lakeside Bed & Breakfast

3.0 star property
The price is AED 889
AED 970 total
includes taxes & fees
15 Apr - 16 Apr
Pressey House Lakeside Bed & Breakfast
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

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
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
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.

Frequently asked questions

What is Oakland like for a resort vacation?
You deserve a getaway, and a resort is the perfect place to treat yourself to the services and amenities you need for a relaxing stay in Oakland. One of the comfortable resorts in the surrounding area could be just what you’re searching for, whether you’re hoping for great restaurants on site, blissful spa treatments, or activities for the kids.
What's a favorite resort in Oakland?
Here are our top-rated resorts around Oakland: Island Glamping in a Luxury Tent in Maine - Beach resort. 22.9 mi (36.9 km) from Oakland. Features free self parking. Eco-Island Resort:14 Private Acres, 5 Unique Stays - Beach resort. 23 mi (37 km) from Oakland.
What can I do in Oakland?
Belgrade Lakes Chain and Tree Spirits are a few of the interesting sights to visit. Other attractions in the area include Colby College and Thomas College.
What's the weather like in Oakland?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Oakland are January, March, December, and February, with each month seeing an average of 9 inches of snowfall.
What's the best way to get to and around Oakland?
Fly into Waterville, ME (WVL-Robert Lafleur), which is located 2.1 mi (3.4 km) away from the heart of the city. You can also search for flights into Augusta, ME (AUG-Augusta State), which is 15.8 mi (25.4 km) away. If you’d like to explore around the area, you may want to rent a car for your trip.