Oakland, ME Vacation Homes from AED 595

A lake surrounded by trees with autumn leaves.

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Our top choices for Oakland vacation homes

Discover Oakland charm near Colby College 10 min

Oakland

Vicki W.

AED 773 total

includes taxes & fees

12 Jul - 13 Jul

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Oakland

Benjamin C.

AED 1,828 total

includes taxes & fees

29 Jul - 30 Jul

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

Madison

Scott

AED 595 total

includes taxes & fees

2 Jul - 3 Jul

The StarGazer Floating Dome

Monmouth

AED 920 total

includes taxes & fees

30 Jun - 1 Jul

Hammock Haven Island Dome

Monmouth

BlairR

AED 801 total

includes taxes & fees

30 Jun - 1 Jul

Island Aframe Adventure in Maine

Monmouth

Robert

AED 1,017 total

includes taxes & fees

19 Jul - 20 Jul

Cozy Cottage on water's edge of Lake Cobbosseecontee

Manchester

Laura Q.

AED 1,329 total

includes taxes & fees

30 Jun - 1 Jul

Rustic Tiny Cabin Getaway Near ATV Trails, Maine

Madison

AED 809 total

includes taxes & fees

6 Jul - 7 Jul

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Top Oakland Hotel Reviews

Fireside Inn & Suites Waterville

8/10 Good

"Nice hot tub. I was pleasantly surprised by this property. Only 2 star but quite nice. The breakfast was grab and go but plenty of options."

Holiday Inn Express & Suites Waterville - North by IHG

8/10 Good

"The Wi-Fi was not good. It was fine in the lobby but only ok in my 4th floor room. The stair towers had hand rails only on the outside wall. There should be hand rails on the inside wall as well. The lounge chair/sofa in our room was not selected for it's usefulness, a couple of chairs would have been preferred. The room and the facility in general was well keep and clean. The staff was helpful and polite. The breakfast was excellent and presented well. The AC functioned well."

The Skowhegan By Kasa

10/10 Excellent

"This is the third time we have stayed here. We were in love after our first visit. It’s nice to see Skowhegan have a nice new place to stay. We love that they turned an old mill building into a hotel. The rooms are great, plenty of room for my small family of 3. The rooms are bigger than a standard hotel room. Prices have been great also. My only complaint is the TV’s. 2 out of the 3 stays we’ve had trouble with the tv’s they function fine, but they always freeze, we think it could be the wi-fi connections. TV in the living area worked perfect but tv in the bedroom kept freezing. But definitely not a reason to not return, it’s in a brick building we understand it can’t be perfect. Didn’t check out the bar but they had a live band which is great. Check in and check out was great with no complications. I actually enjoy the contactless check in and check out."

Lockwood Hotel

8/10 Good

"Loved the industrial design of the hotel, natural ME pine wood. Their website should note entrance is actually on Front Street, not Main. I went around 3 times until I found the entrance(parking across the street.) Copley College involved in the hotel, branch of their museum up the street. I went back to Waterville(childhood vacation), to go the Colby free museum, so great! All in all, Waterville is back and worth a visit. I noted to staff at hotel the bar staff, one young woman, should pay attention to the guests in front of them, not fooling around with a new recipe, ignoring everything else. I worked for The Ritz Carlton Co. over 6 years, it’s important you know who pays your paycheck."

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation homes

Discover Oakland charm near Colby College 10 min

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!