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

Apartment in Oakland

Central Maine Apartment offering 4 Seasons of Fun.
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
Jan 21 - Jan 22
Central Maine Apartment offering 4 Seasons of Fun.
2 bedrooms, WiFi, bed sheets

Apartment in Oakland

The heart of the Belgrade Lakes
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 1 - Feb 2
The heart of the Belgrade Lakes
Exterior

Vacation Home in Oakland

Discover Oakland charm near Colby College 10 min
2.0 star property
10.0 out of 10, Exceptional, (6 reviews)
"New, clean and had everything we needed. "
United States
Lara B.
The price is ￥14,088
￥40,692 total
includes taxes & fees
Jan 21 - Jan 22
Discover Oakland charm near Colby College 10 min
Exterior

Vacation Home in Oakland

Cozy getaway: farmhouse with wood stove & jacuzzi tub
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 21 - Jan 22
Cozy getaway: farmhouse with wood stove & jacuzzi tub
TV

Cabin in Oakland

NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
The price is ￥22,769
￥46,534 total
includes taxes & fees
Jan 21 - Jan 22
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
Exterior

Cabin in Skowhegan

The Cabin 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
Jan 21 - Jan 22
The Cabin Skowhegan
Interior

Apartment in Hallowell

High End Apartment in Downtown 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 21 - Jan 22
High End Apartment in Downtown Hallowell
Property grounds

Cabin in Madison

Private cabin on 30 acres, close to skiing, snowmobile & amenities
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is ￥19,765
￥53,773 total
includes taxes & fees
Jan 21 - Jan 22
Private cabin on 30 acres, close to skiing, snowmobile & amenities
Outdoor dining

Apartment in Waterville

Minutes to Colby
8.8 out of 10, Excellent, (22 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is ￥17,235
￥29,989 total
includes taxes & fees
Jan 21 - Jan 22
Minutes to Colby
Exterior

Condo in Pittsfield

Angel Mist Retreat Garage Apartment
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
Jan 21 - Jan 22
Angel Mist Retreat Garage Apartment
Exterior

Vacation Home in Madison

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
9.0 out of 10, Wonderful, (4 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is ￥19,212
￥24,389 total
includes taxes & fees
Feb 2 - Feb 3
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Interior

Cottage in Belgrade

Ice Fishing, Dog Friendly, Lake Great Pond
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 ￥24,115
￥54,724 total
includes taxes & fees
Jan 26 - Jan 27
Ice Fishing, Dog Friendly, Lake Great Pond
Property grounds

Vacation Home in Manchester

Cozy Cottage on water's edge of Lake Cobbosseecontee
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
Jan 21 - Jan 22
Cozy Cottage on water's edge of Lake Cobbosseecontee
Dining

Vacation Home in Sidney

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

Vacation Home in Belgrade

Family's Paradise: 3BR/2BA,Game Room & Lake Access
2.0 star property
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is ￥37,474
￥138,225 total
includes taxes & fees
Jan 21 - Jan 22
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Outdoor dining

Cottage in Manchester

Lighthouse Lane
10.0 out of 10, Exceptional, (70 reviews)
"Very nice stay Beautiful lake views "
United States
Karen G.
The price is ￥35,577
￥49,292 total
includes taxes & fees
Jan 21 - Jan 22
Lighthouse Lane
Property grounds

Vacation Home in Wayne

Every window has a spectacular lake view Low fees
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 ￥32,019
￥59,375 total
includes taxes & fees
Jan 21 - Jan 22
Every window has a spectacular lake view Low fees
On the beach

Vacation Home in Burnham

The Maine Lake House with an Amazing Sand Beach!
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 ￥31,387
￥81,598 total
includes taxes & fees
Jan 21 - Jan 22
The Maine Lake House with an Amazing Sand Beach!
Outdoor spa tub

Apartment in Whitefield

Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
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
￥44,639 total
includes taxes & fees
Jan 21 - Jan 22
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior detail

Aparthotel in wilton

Spacious King Room with AC, WiFi in Peaceful Wilton
The price is ￥27,039
￥33,781 total
includes taxes & fees
Jan 21 - Jan 22
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 12 hours 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:

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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.