Oakland Vacation Rentals from ￥49,187: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Oakland?

Cozy getaway: farmhouse with wood stove & jacuzzi tub : This Oakland vacation home rental is located in a rural location and has an outdoor pool, a patio, and a barbecue grill to put you at ease 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. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Cozy Long Pond Cottage: community access, private mooring & shared dock. as a favorite home for rent in Oakland.

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Our top choices for Oakland vacation rentals

Central Maine Apartment offering 4 Seasons of Fun.

Oakland

Norbert A.

￥39,728 total

includes taxes & fees

Mar 11 - Mar 12

Discover Oakland charm near Colby College 10 min

Oakland

Vicki W.

￥40,948 total

includes taxes & fees

Mar 15 - Mar 16

The heart of the Belgrade Lakes

Oakland

Maureen

￥36,976 total

includes taxes & fees

Apr 1 - Apr 2

Peaceful Farmhouse Retreat- Pets welcome

Oakland

Andrea C.

￥60,064 total

includes taxes & fees

Mar 15 - Mar 16

The Cabin Skowhegan

Skowhegan

Mary D.

￥33,192 total

includes taxes & fees

Mar 11 - Mar 12

Charming cabin in the birches right on the atv trail!

Fairfield

Lisa O.

￥20,122 total

includes taxes & fees

Mar 11 - Mar 12

Two bedroom Mid Century Modern apartment in Downtown Hallowell

Hallowell

Rebekah B.

￥37,664 total

includes taxes & fees

Mar 15 - Mar 16

Angel Mist Retreat Garage Apartment

Pittsfield

Rob K.

￥48,740 total

includes taxes & fees

Mar 11 - Mar 12

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Top Oakland Hotel Reviews

Holiday Inn Express & Suites Waterville - North by IHG

8/10 Good

"Good for area, no issues at any point."

The Elmwood

4/10 Poor

"I would not stay there again. Sort or mostly remodeled but not complete or at least some things done properly . Reminded me of roadside dive ok for one single night and definitely not worth the money I paid. Definitely not one place you forget the world around you. Not well lit at night . Next to highway. Not exactly exuding safe feeling."

The Skowhegan By Kasa

4/10 Poor

"This place at first look is super nice. If you stayed just for a night two you would probably not be phased. We stayed here for 3 weeks while we had water damage remediation at our house. We had a deluxe room with a king size bed and a separate living area with a sofa bed. There were 4 of us, myself, husband and two kids. So my first complaint is that the coffee table you need to move to pull out the sofa bed literally weighs 200 lbs. They can call it a room that sleeps 4 but it was really not functional. The room had a stovetop and refrigerator but was advertised as a “kitchenette.” The only microwave was downstairs and didn’t work. The only heat is the bedroom so if the door was closed the bedroom would get really hot and the living room would get cold. This place is more Airbnb style, you couldn’t get toilet or towels unless it was before 3. That was fine after we figured it out. There were quite a few times that we ran out things like toilet paper, trash bags, towels etc. and it was after employee hours. Would have been nice to know ahead of time that after 3 pm those things are not available. Also there is no place to get rid of trash, again found this out after hours. We were told to leave it inside our room and someone would pick it up the next day. This was just annoying, other rooms started putting it out in the hall. Be prepared to receive constant texts about "

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

10/10 Excellent

"This is an amazing property and our stay was perfect! The property was VERY clean, modern, and met all of our needs (& more!). The host was very responsive to our questions and messages and we felt extremely welcome. The host even put out water and food bowls and a bed for our two black labs! The view is amazing and we were able to enjoy watching snowmobiles having adventures on the lake. We absolutely recommend this property to anyone staying in the Belgrade Lakes area at any season! "

Find out more about Oakland

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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?

Cozy getaway: farmhouse with wood stove & jacuzzi tub: This Oakland vacation home rental is located in a rural location and has an outdoor pool, a patio, and a barbecue grill to put you at ease 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. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Cozy Long Pond Cottage: community access, private mooring & shared dock. as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 30 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.

Oakland Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation rentals

Central Maine Apartment offering 4 Seasons of Fun.

Discover Oakland charm near Colby College 10 min

The heart of the Belgrade Lakes

Peaceful Farmhouse Retreat- Pets welcome

The Cabin Skowhegan

Charming cabin in the birches right on the atv trail!

Two bedroom Mid Century Modern apartment in Downtown Hallowell

Angel Mist Retreat Garage Apartment

Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths

Ice Fishing, Dog Friendly, Lake Great Pond

Cozy Cottage on water's edge of Lake Cobbosseecontee

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP

Family's Paradise: 3BR/2BA,Game Room & Lake Access

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

Minutes to Colby

Every window has a spectacular lake view Low fees

Spacious modern living in a quite neighborhood

Lighthouse Lane

High End Apartment in Downtown Hallowell

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Holiday Inn Express & Suites Waterville - North by IHG

Find out more about Oakland

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