Oakland Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

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$2,046 total
includes taxes & fees
27 Apr - 28 Apr
Sister A-Frame in Woods B
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$1,836 total
includes taxes & fees
2 May - 3 May
The heart of the Belgrade Lakes
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$916
HK$1,793 total
includes taxes & fees
26 Apr - 27 Apr
Discover Oakland charm near Colby College 10 min
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, (44 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is HK$791
HK$1,887 total
includes taxes & fees
7 May - 8 May
Central Maine Apartment offering 4 Seasons of Fun.
Exterior

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway

Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very accommodating host. Loved everything about it. Highly recommend "
United States
Mike M.
The price is HK$1,371
HK$2,602 total
includes taxes & fees
29 Apr - 30 Apr
Pool, fire pit & dogs welcome, close to lakes and trails - Maine Farm Getaway
TV

Cozy home tranquil wooded setting walking trails stream frontage in Wilton WiFi

Cozy home tranquil wooded setting walking trails stream frontage in Wilton WiFi
Wilton
The price is HK$744
HK$1,494 total
includes taxes & fees
27 Apr - 28 Apr
Cozy home tranquil wooded setting walking trails stream frontage in Wilton WiFi
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$783
HK$1,622 total
includes taxes & fees
29 Apr - 30 Apr
The Cabin Skowhegan
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$595
HK$1,981 total
includes taxes & fees
3 May - 4 May
Island Aframe Adventure in Maine
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, (43 reviews)
"The cabin amd property were fantastic! Secluded location, loved the fire pit. Great central location for out door activities. "
United States
Susan Appt E.
The price is HK$1,018
HK$2,698 total
includes taxes & fees
26 Apr - 27 Apr
Cabin on 30 acre of privacy. Fire pit, picnic table, trails & close to town.
Terrace/patio

The Beach Bum | Modern Cabin on the Sand

The Beach Bum | Modern Cabin on the Sand
Burnham
10.0 out of 10, Exceptional, (2 reviews)
"Nice cottage. Perfect location. Everything you need for a quiet beach stay on Unity pond. "
United States
Albert
The price is HK$1,299
HK$3,163 total
includes taxes & fees
26 Apr - 27 Apr
The Beach Bum | Modern Cabin on the Sand
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$881
HK$1,345 total
includes taxes & fees
26 Apr - 27 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)
"We like this property so much—-it was our second time staying! This apartment is spacious and comfortable. It is located in town and walking distance from small shops and quality restaurants. "
United States
jessica b.
The price is HK$1,018
HK$1,912 total
includes taxes & fees
26 Apr - 27 Apr
Two bedroom Mid Century Modern apartment in Downtown Hallowell
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$1,443 total
includes taxes & fees
2 May - 3 May
Cozy cottage in the Winthrop Lakes Area
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$2,411 total
includes taxes & fees
2 May - 3 May
Angel Mist Retreat Garage Apartment
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$740
HK$978 total
includes taxes & fees
28 Apr - 29 Apr
Paddle, float, fish, or rope swing into the near by crystal clear mountain lake.
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$2,638 total
includes taxes & fees
26 Apr - 27 Apr
Cozy Cottage on water's edge of Lake Cobbosseecontee
Exterior detail

Spacious modern living in a quite neighborhood

Spacious modern living in a quite neighborhood
Madison
The price is HK$1,005
HK$1,266 total
includes taxes & fees
26 Apr - 27 Apr
Spacious modern living in a quite neighborhood
Interior

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Winthrop
The price is HK$1,175
HK$2,169 total
includes taxes & fees
26 Apr - 27 Apr
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Interior

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Belgrade
10.0 out of 10, Exceptional, (53 reviews)
"Great location!"
United States
Gail D.
The price is HK$1,068
HK$2,540 total
includes taxes & fees
3 May - 4 May
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Terrace/patio

Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
10.0 out of 10, Exceptional, (3 reviews)
"Could not have asked for a better way to end our vacation than a visit to this island. For being a sustainable space it does not lack in amenities conducive to comfort, and the setting is pristine. I had particular fondness for the rope swing!!"
United States
BlairR
The price is HK$462
HK$1,656 total
includes taxes & fees
3 May - 4 May
Hammock Haven Island Dome
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

4/10 Poor
"Room walls were quite thin. I heard the individual snoring in the room next door and also felt my headboard move as they got into bed in the room next door. Gym is very basic. Staff are excellent and breakfast is not that diverse."
Akshay 2-night trip
Posted 9 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
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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!

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 Charming 3 bedroom guest house on farm as a favourite home for rent in Oakland.

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.