Oakland Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Oakland holiday rentals

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$629
HK$1,495 total
includes taxes & fees
18 Feb - 19 Feb
The heart of the Belgrade Lakes
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$943
HK$1,786 total
includes taxes & fees
3 Mar - 4 Mar
Sister A-Frame in Woods B
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$821
HK$1,900 total
includes taxes & fees
1 Mar - 2 Mar
Central Maine Apartment offering 4 Seasons of Fun.
Exterior

Cozy getaway: farmhouse with wood stove & jacuzzi tub

Cozy getaway: farmhouse with wood stove & jacuzzi tub
Oakland
10.0 out of 10, Exceptional, (9 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$1,524
HK$2,865 total
includes taxes & fees
23 Feb - 24 Feb
Cozy getaway: farmhouse with wood stove & jacuzzi tub
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$696
HK$1,986 total
includes taxes & fees
1 Mar - 2 Mar
Discover Oakland charm near Colby College 10 min
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$782
HK$1,653 total
includes taxes & fees
1 Mar - 2 Mar
The Cabin Skowhegan
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, (82 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$938
HK$1,797 total
includes taxes & fees
22 Feb - 23 Feb
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.0 out of 10, Wonderful, (6 reviews)
"Very neat cabin. Spacious all utilities and a fire pit"
United States
Lisa O.
The price is HK$703
HK$1,150 total
includes taxes & fees
1 Mar - 2 Mar
Charming cabin in the birches right on the atv trail!
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$1,097
HK$2,355 total
includes taxes & fees
9 Mar - 10 Mar
Angel Mist Retreat Garage Apartment
Property grounds

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

Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Everything was amazing"
United States
Antwan B.
The price is HK$1,196
HK$2,922 total
includes taxes & fees
18 Feb - 19 Feb
Private cabin, 30 acres, 40 min to Sugarloaf. Can snowmobile, ATV and hike paths
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, (19 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$1,133
HK$2,632 total
includes taxes & fees
19 Feb - 20 Feb
Cozy Cottage on water's edge of Lake Cobbosseecontee
Interior

Ice Fishing, Dog Friendly, Lake Great Pond

Ice Fishing, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (50 reviews)
"Great location!"
United States
Gail D.
Ice Fishing, Dog Friendly, Lake Great Pond
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 HK$950
HK$1,205 total
includes taxes & fees
19 Feb - 20 Feb
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
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$1,446
HK$2,215 total
includes taxes & fees
20 Feb - 21 Feb
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is HK$950
HK$1,205 total
includes taxes & fees
18 Feb - 19 Feb
Spacious modern living in a quite neighborhood
Terrace/patio

The Escape | Steps to the Sand

The Escape | Steps to the Sand
Burnham
The price is HK$1,296
HK$3,198 total
includes taxes & fees
18 Feb - 19 Feb
The Escape | Steps to the Sand
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$1,477
HK$6,365 total
includes taxes & fees
18 Feb - 19 Feb
Family's Paradise: 3BR/2BA,Game Room & Lake Access
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$1,449
HK$2,772 total
includes taxes & fees
18 Feb - 19 Feb
Every window has a spectacular lake view Low fees
Outdoor dining

Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (22 reviews)
"Easy check in and spacious apartment. Excellent location- within minutes of Colby and downtown restaurants. Super comfy living room to relax in after a full day of Parents Weekend:"
United States
Jodie M.
The price is HK$860
HK$1,499 total
includes taxes & fees
24 Feb - 25 Feb
Minutes to Colby
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

Comfort Inn & Suites Wilton

Comfort Inn & Suites Wilton

10/10 Excellent
"Clean room and friendly staff"
James 1-night trip
Posted 2 days ago
Comfort Inn & Suites Wilton

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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  • 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!

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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. Our travellers also rate Cozy getaway: farmhouse with wood stove & jacuzzi tub as a favourite home for rent in Oakland.

How many holiday rentals will I find in Oakland?

Choose from 29 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.