Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Oakland vacation rentals

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 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is ￥15,970
￥38,089 total
includes taxes & fees
Feb 3 - Feb 4
Central Maine Apartment offering 4 Seasons of Fun.
2 bedrooms, WiFi, bed sheets

The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (9 reviews)
"Host was very accommodating "
United States
Maureen
The price is ￥18,184
￥37,056 total
includes taxes & fees
Feb 3 - Feb 4
The heart of the Belgrade Lakes
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
2.0 star property
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"New, clean and had everything we needed. "
United States
Lara B.
The price is ￥14,088
￥40,347 total
includes taxes & fees
Feb 1 - Feb 2
Discover Oakland charm near Colby College 10 min
Exterior

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (8 reviews)
"It was that was said to be The host was very nice and helpful . I enjoyed my stay "
United States
Andrea C.
The price is ￥30,833
￥57,960 total
includes taxes & fees
Jan 24 - Jan 25
Cozy getaway: farmhouse with wood stove & jacuzzi tub
TV

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 ￥22,769
￥46,190 total
includes taxes & fees
Jan 30 - Jan 31
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (50 reviews)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is ￥15,812
￥33,264 total
includes taxes & fees
Feb 1 - Feb 2
The Cabin Skowhegan
Interior

High End Apartment in Downtown Hallowell

High End Apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (98 reviews)
"Beautiful place to stay. Having coffee with all the fixings already there along with snacks was great! Would definitely stay here again!"
United States
John H.
The price is ￥17,709
￥32,574 total
includes taxes & fees
Jan 28 - Jan 29
High End Apartment in Downtown Hallowell
Property grounds

Private cabin on 30 acres, close to skiing, snowmobile & amenities

Private cabin on 30 acres, close to skiing, snowmobile & amenities
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is ￥19,765
￥53,429 total
includes taxes & fees
Feb 1 - Feb 2
Private cabin on 30 acres, close to skiing, snowmobile & amenities
Outdoor dining

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is ￥17,243
￥30,003 total
includes taxes & fees
Jan 21 - Jan 22
Minutes to Colby
Exterior

Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (14 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is ￥22,200
￥48,672 total
includes taxes & fees
Feb 1 - Feb 2
Angel Mist Retreat Garage Apartment
Exterior

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.0 out of 10, Wonderful, (4 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is ￥19,220
￥24,399 total
includes taxes & fees
Feb 2 - Feb 3
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Interior

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (49 reviews)
"Great place for us to get in 2 days of golf and 2 days of fishing. House was clean and communication with host prior to arrival and during our stay was excellent. "
United States
Thomas B.
The price is ￥23,966
￥54,574 total
includes taxes & fees
Jan 25 - Jan 26
Ice Fishing, Dog Friendly, Lake Great Pond
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 reviews)
"Very quiet spot right on the lake, relatively easy to get to, close to town. Cabin is small, which was perfect for the two of us. "
United States
Stephanie P.
The price is ￥22,927
￥53,084 total
includes taxes & fees
Feb 2 - Feb 3
Cozy Cottage on water's edge of Lake Cobbosseecontee
Dining

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

Spacious Country Home w/ Hot Tub, near Colby/Thomas
Sidney
9.6 out of 10, Exceptional, (39 reviews)
"Wonderful location and beautiful property, very peaceful and convenient "
United States
Anne M.
The price is ￥18,342
￥54,281 total
includes taxes & fees
Feb 1 - Feb 2
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Terrace/patio

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

Family's Paradise: 3BR/2BA,Game Room & Lake Access
2.0 star property
Belgrade
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is ￥35,909
￥136,390 total
includes taxes & fees
Jan 21 - Jan 22
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Outdoor dining

Lighthouse Lane

Lighthouse Lane
Manchester
10.0 out of 10, Exceptional, (70 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is ￥35,577
￥49,120 total
includes taxes & fees
Feb 2 - Feb 3
Lighthouse Lane
Property grounds

Every window has a spectacular lake view Low fees

Every window has a spectacular lake view Low fees
Wayne
9.8 out of 10, Exceptional, (45 reviews)
"Tina was great and very informative with places to visit and place to eat. Will definitely be checking in again "
United States
Nancy
The price is ￥28,047
￥54,367 total
includes taxes & fees
Jan 21 - Jan 22
Every window has a spectacular lake view Low fees
On the beach

The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!
Burnham
8.8 out of 10, Excellent, (6 reviews)
"Great stay, property was a great fit for a few day stay to visit family."
United States
Amy M.
The price is ￥31,401
￥81,634 total
includes taxes & fees
Jan 21 - Jan 22
The Maine Lake House with an Amazing Sand Beach!
Outdoor spa tub

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

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Whitefield
10.0 out of 10, Exceptional, (6 reviews)
"Great getaway! We loved all of the discoveries to be made both in the cabin and on the property. We stayed in Stella. It was adorable, functional, and very welcoming. We also enjoyed an outing to Kennebec Maine Cabin Masters only 20 min away! "
United States
Sandra L.
The price is ￥29,252
￥43,777 total
includes taxes & fees
Feb 1 - Feb 2
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior detail

Spacious King Room with AC, WiFi in Peaceful Wilton

Spacious King Room with AC, WiFi in Peaceful Wilton
wilton
The price is ￥27,039
￥33,781 total
includes taxes & fees
Jan 23 - Jan 24
Spacious King Room with AC, WiFi in Peaceful Wilton
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

Hampton Inn Waterville

Hampton Inn Waterville

10/10 Excellent
"Clean room, great staff!!! Loved coffee in the entry area too, thank you!!"
Cheryl 1-night trip
Posted 1 day ago
Hampton Inn Waterville

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
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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?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This Oakland vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Beautiful lakeside 4 bedroom retreat with private dock and walkout basement as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 28 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.