Photo by Marc Maheu

Oakland Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Oakland

Fridge, oven, stovetop, dishwasher
Classy AF Home Steps from Colby and Trails

Classy AF Home Steps from Colby and Trails

Oakland
10.0 out of 10, Exceptional, (49)
"Clean, comfortable and incredibly close to campus for a college visit."
United States
Patricia R.
Classy AF Home Steps from Colby and Trails
Outdoor dining
Cozy Long Pond Cottage: private mooring & shared dock.

Cozy Long Pond Cottage: private mooring & shared dock.

Rome
9.8 out of 10, Exceptional, (20)
"We had a great time kayaking on the lake and enjoying the beach. The house had plenty of room to get together with family for dinners. The house is well equipped and very comfortable."
United States
Jim U.
Cozy Long Pond Cottage: private mooring & shared dock.
Exterior
Sister A-Frame in Woods B

Sister A-Frame in Woods B

Oakland
10.0 out of 10, Exceptional, (8)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$939
HK$1,779 total
includes taxes & fees
2 Dec - 3 Dec
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)
"The place was clean, very spacious and comfortable. Having the laundry was helpful, so I didn’t have to worry about doing laundry when I got home late (also, I spilled coffee on the way there, so I’m glad the stain was gone)."
United States
Keeko
The price is HK$817
HK$1,918 total
includes taxes & fees
2 Dec - 3 Dec
Central Maine Apartment offering 4 Seasons of Fun.
Interior
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Oakland
9.2 out of 10, Wonderful, (26)
"Adorable cabin well stocked with plenty of space. Beautiful view! Nice and Clean. Needed help with the door lock and they were quick to respond and help. "
United States
Angela
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Front of property
My Valhalla Farm

My Valhalla Farm

3.5 star property
Oakland
The price is HK$1,752
HK$2,688 total
includes taxes & fees
2 Dec - 3 Dec
My Valhalla Farm
Property grounds
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2.0 star property
Oakland
10.0 out of 10, Exceptional, (4)
"We had an excellent stay on the lake. The property is beautiful and the house has everything, with great views from all 3 levels. We would love to stay again! "
United States
Ashley L.
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
Fridge, microwave, stovetop, coffee/tea maker
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 HK$1,212
HK$2,433 total
includes taxes & fees
2 Dec - 3 Dec
NEW Cozy Cabin located in Oakland tucked away in a peaceful wooded scene.
TV
Spacious Country Home w/ Hot Tub, near Colby/Thomas

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

Sidney
9.8 out of 10, Exceptional, (35)
"Very nice hot tub, quite and beautiful area! Air quality amazing and AC works fantasticly!"
United States
Nathan
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Property grounds
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
Readfield
10.0 out of 10, Exceptional, (7)
"It was a wonderful week. The cabin is very well appointed. We lacked for nothing! Thank you "
United States
Gigi A.
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !
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, (137)
"Very relaxing!"
United States
Bradford B.
The price is HK$701
HK$933 total
includes taxes & fees
2 Dec - 3 Dec
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
8.6 out of 10, Excellent, (18)
"Check in was a breeze. Right on the lake. House was just the right size for me and my 3 adult sons. Was lovely to paddle, canoe or swim just walking down the porch stairs"
United States
Heather A.
The price is HK$1,016
HK$2,482 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Cottage on water's edge of Lake Cobbosseecontee
Fridge, microwave, oven, stovetop
Large Secluded Cabin on the Lake - Now booking 2+ night stays

Large Secluded Cabin on the Lake - Now booking 2+ night stays

Smithfield
10.0 out of 10, Exceptional, (66)
"Great vacation with 3 generations of our family. House was beautiful, lake clean with great swimming and fishing. Hope to return for years to come. "
United States
David M.
Large Secluded Cabin on the Lake - Now booking 2+ night stays
Fridge, microwave, oven, stovetop
Lakefront Cabin

Lakefront Cabin

China
10.0 out of 10, Exceptional, (27)
"Very clean, great view, quiet, serene location right on the lake."
United States
katherine b.
Lakefront Cabin
Property grounds
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
9.8 out of 10, Exceptional, (86)
"Absolutely amazing property, everything we were looking for and an amazing host too! Highly recommend! "
United States
samantha c.
Private and Calming Waterfront to the Rescue!
Outdoor spa tub
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly

Manchester
10.0 out of 10, Exceptional, (254)
"We had a fantastic time! The lake is beautiful and the house has everything you need to enjoy it. "
United States
Dave S.
Spectacular Cobbossee Lakefront with Hot Tub & Dog Friendly
Property grounds
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards

Whitefield
9.8 out of 10, Exceptional, (30)
"We stayed in this cabin for two nights with our dog and it was very peaceful and fun! The cabin has a campfire, lots of batteries for charging, lights, battery fans, etc. There were many long walking trails with fun activities; like kayaking, axe throwing, a pizza oven… Exactly what we were looking for! Would stay again! "
United States
Ben R.
The price is HK$1,168
HK$1,748 total
includes taxes & fees
2 Dec - 3 Dec
Tiny Cabin with Private Hot Tub on 100 Acres Kayaks, Canoes & Paddleboards
Terrace/patio
The Cabin Skowhegan

The Cabin Skowhegan

Skowhegan
9.8 out of 10, Exceptional, (50)
"Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money."
United States
Sue
The price is HK$779
HK$1,638 total
includes taxes & fees
2 Dec - 3 Dec
The Cabin Skowhegan
Dining
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Albion
9.8 out of 10, Exceptional, (37)
"Nice place, great fishing. "
United States
Bryan W.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Interior
NEW! Long Pond Lake View Getaway w/HOT TUB, ME

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

Mount Vernon
10.0 out of 10, Exceptional, (2)
"This house was absolutely stunning! Had absolutely everything that you needed the house offered everything that one would need and plenty of space for everybody! The game room was so fun! The hot tub was a great bonus! Everyone had an amazing time while staying."
United States
Rachael L.
NEW! Long Pond Lake View Getaway w/HOT TUB, ME
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
"Everything was wonderful. An improvement would be to have a small trash bin in the bathroom to throw hiny wipes away without walking across the entire bedroom. Plus people shouldn’t flush them. Makes sense to me."
Stephen 1-night trip
Posted 6 days 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!

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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?

Classy AF Home Steps from Colby and Trails: This highly rated holiday home rental in Oakland offers a private garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Our travellers also rate Cozy Long Pond Cottage: private mooring & shared dock 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.