Oakland Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Oakland holiday rentals

Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$945
HK$1,791 total
includes taxes & fees
15 Apr - 16 Apr
Sister A-Frame in Woods B
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$776
HK$1,632 total
includes taxes & fees
15 Apr - 16 Apr
Discover Oakland charm near Colby College 10 min
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 HK$901
HK$1,845 total
includes taxes & fees
26 Apr - 27 Apr
The heart of the Belgrade Lakes
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 HK$823
HK$1,931 total
includes taxes & fees
5 Apr - 6 Apr
Central Maine Apartment offering 4 Seasons of Fun.
Exterior

Charming 3 bedroom guest house on farm

Charming 3 bedroom guest house on farm
Oakland
10.0 out of 10, Exceptional, (11 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 HK$1,647
HK$3,159 total
includes taxes & fees
12 Apr - 13 Apr
Charming 3 bedroom guest house on farm
Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (52 reviews)
"Very quiet and relaxing - just what we wanted."
United States
Mary D.
The price is HK$784
HK$1,640 total
includes taxes & fees
9 Apr - 10 Apr
The Cabin Skowhegan
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.2 out of 10, Wonderful, (7 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
The price is HK$882
HK$1,346 total
includes taxes & fees
17 Apr - 18 Apr
Charming cabin in the birches right on the atv trail!
TV

Two bedroom Mid Century Modern apartment in Downtown Hallowell

Two bedroom Mid Century Modern apartment in Downtown Hallowell
Hallowell
10.0 out of 10, Exceptional, (83 reviews)
"Great apartment, close to town, very clean, comfortable beds. Loved the little extras too.. coffee, creamer, etc! Will definitely stay again. "
United States
Rebekah B.
The price is HK$1,019
HK$1,905 total
includes taxes & fees
15 Apr - 16 Apr
Two bedroom Mid Century Modern apartment in Downtown Hallowell
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 HK$1,100
HK$2,438 total
includes taxes & fees
5 Apr - 6 Apr
Angel Mist Retreat Garage Apartment
Property grounds

Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.

Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is HK$1,019
HK$2,640 total
includes taxes & fees
12 Apr - 13 Apr
Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.
Terrace/patio

Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.6 out of 10, Exceptional, (4 reviews)
"Lovely cottage! Everything we needed. The hosts were gracious and communicated well."
United States
Joshua
The price is HK$815
HK$1,444 total
includes taxes & fees
10 Apr - 11 Apr
Cozy cottage in the Winthrop Lakes Area
Exterior

Island Aframe Adventure in Maine

Island Aframe Adventure in Maine
Monmouth
10.0 out of 10, Exceptional, (6 reviews)
"A very pleasant, peaceful place to stay. The hosts were very proactive about making sure we had a great stay and did everything to could to make it as stress-free as possible."
United States
Robert
The price is HK$894
HK$2,341 total
includes taxes & fees
3 May - 4 May
Island Aframe Adventure in Maine
Interior

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (52 reviews)
"Great location!"
United States
Gail D.
The price is HK$1,132
HK$2,610 total
includes taxes & fees
8 Apr - 9 Apr
Ice Fishing, Dog Friendly, Lake Great Pond
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 HK$1,411
HK$2,187 total
includes taxes & fees
6 Apr - 7 Apr
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Property grounds

Cozy Cottage on water's edge of Lake Cobbosseecontee

Cozy Cottage on water's edge of Lake Cobbosseecontee
Manchester
8.8 out of 10, Excellent, (21 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 HK$1,136
HK$2,640 total
includes taxes & fees
10 Apr - 11 Apr
Cozy Cottage on water's edge of Lake Cobbosseecontee
Exterior

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.2 out of 10, Wonderful, (5 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is HK$952
HK$1,209 total
includes taxes & fees
16 Apr - 17 Apr
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Terrace/patio

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

Family's Paradise: 3BR/2BA,Game Room & Lake Access
Belgrade
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay."
United States
Tyson W.
The price is HK$1,364
HK$6,237 total
includes taxes & fees
5 Apr - 6 Apr
Family's Paradise: 3BR/2BA,Game Room & Lake Access
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is HK$952
HK$1,209 total
includes taxes & fees
5 Apr - 6 Apr
Spacious modern living in a quite neighborhood
Exterior

Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.

Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
Strong
9.4 out of 10, Exceptional, (138 reviews)
"Nice little cottage at a good price, thank you! "
United States
Jacob Z.
The price is HK$839
HK$1,085 total
includes taxes & fees
27 Apr - 28 Apr
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
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 HK$1,404
HK$2,718 total
includes taxes & fees
10 Apr - 11 Apr
Every window has a spectacular lake view Low fees
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Good"
Vilmarie 1-night trip
Posted 10 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Oakland has to offer?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Oakland are Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views! and Peaceful Farmhouse Retreat- Pets welcome.

How many holiday rentals will I find in Oakland?

Choose from 30 Expedia holiday rentals in Oakland for a memorable holiday.

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 wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.