Daybreak at lake, United States, Maine, Oakland

Oakland Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Oakland holiday rentals

Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is HK$776
HK$1,648 total
includes taxes & fees
9 Jul - 10 Jul
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, (47 reviews)
"Great hiking - nice views."
United States
Norbert A.
The price is HK$823
HK$1,922 total
includes taxes & fees
15 Jun - 16 Jun
Central Maine Apartment offering 4 Seasons of Fun.
Outdoor dining

Pool, fire pit & minutes to Messalonskee Lake!

Pool, fire pit & minutes to Messalonskee Lake!
Oakland
10.0 out of 10, Exceptional, (12 reviews)
"It was a great stay. The house is very comfortable"
United States
Benjamin C.
The price is HK$1,959
HK$3,329 total
includes taxes & fees
21 Jun - 22 Jun
Pool, fire pit & minutes to Messalonskee Lake!
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
13 Jul - 14 Jul
The heart of the Belgrade Lakes
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, (22 reviews)
"Location is amazing "
United States
Laura Q.
The price is HK$1,293
HK$2,836 total
includes taxes & fees
14 Jun - 15 Jun
Cozy Cottage on water's edge of Lake Cobbosseecontee
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$2,412 total
includes taxes & fees
14 Jun - 15 Jun
Angel Mist Retreat Garage Apartment
On the beach

The Getaway- A Cozy Lakeside Cabin

The Getaway- A Cozy Lakeside Cabin
Burnham
10.0 out of 10, Exceptional, (6 reviews)
"Such a great cabin and location. Super clean and a perfect getaway, we can’t wait to go back!"
United States
Sara D.
The price is HK$1,461
HK$3,647 total
includes taxes & fees
14 Jun - 15 Jun
The Getaway- A Cozy Lakeside Cabin
Interior

Readfield Retreat w/ Lake Maranacook Views!

Readfield Retreat w/ Lake Maranacook Views!
3.0 star property
Readfield
The price is HK$1,677
HK$3,891 total
includes taxes & fees
6 Jul - 7 Jul
Readfield Retreat w/ Lake Maranacook Views!
TV

The Hideout Cabin | Steps to the Beach

The Hideout Cabin | Steps to the Beach
Burnham
10.0 out of 10, Exceptional, (9 reviews)
"Perfect for relaxing"
United States
Diana W.
The price is HK$1,590
HK$3,783 total
includes taxes & fees
16 Jun - 17 Jun
The Hideout Cabin | Steps to the Beach
Property grounds

Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Madison
10.0 out of 10, Exceptional, (44 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$1,167
HK$2,878 total
includes taxes & fees
24 Jun - 25 Jun
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Property grounds

Great Pond Waterfront: Dog-friendly Home Near Colby College

Great Pond Waterfront: Dog-friendly Home Near Colby College
Belgrade
9.8 out of 10, Exceptional, (37 reviews)
"Fantastic rental in all respects, highly recommended."
United States
John S.
Great Pond Waterfront: Dog-friendly Home Near Colby College
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, (55 reviews)
"House was very comfortable and neat! Great location!"
United States
Brian D.
The price is HK$1,638
HK$3,237 total
includes taxes & fees
24 Jun - 25 Jun
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
Exterior

Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!

Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Strong
9.4 out of 10, Exceptional, (141 reviews)
"Nice little cottage at a good price, thank you! "
United States
Jacob Z.
The price is HK$945
HK$1,201 total
includes taxes & fees
18 Jun - 19 Jun
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
On the beach

The Retreat- A Relaxing Beachside Bungalow

The Retreat- A Relaxing Beachside Bungalow
Burnham
10.0 out of 10, Exceptional, (3 reviews)
"Great cabin and location "
United States
John V.
The price is HK$1,299
HK$3,189 total
includes taxes & fees
14 Jun - 15 Jun
The Retreat- A Relaxing Beachside Bungalow
On the beach

The Maine Lake House with an Amazing Sand Beach!

The Maine Lake House with an Amazing Sand Beach!
Burnham
9.0 out of 10, Wonderful, (7 reviews)
"Comfortable & clean!"
United States
Jaime W.
The price is HK$1,658
HK$4,151 total
includes taxes & fees
14 Jun - 15 Jun
The Maine Lake House with an Amazing Sand Beach!
Private kitchen

Wilson Lake Inn

Wilson Lake Inn
2.0 star property
Wilton
The price is HK$1,230
HK$1,341 total
includes taxes & fees
24 Jun - 25 Jun
Wilson Lake Inn
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$846
HK$2,289 total
includes taxes & fees
20 Jun - 21 Jun
Island Aframe Adventure in 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$1,410
HK$2,195 total
includes taxes & fees
24 Jun - 25 Jun
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Exterior

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Winthrop
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay"
United States
Michael Y.
The price is HK$2,292
HK$6,760 total
includes taxes & fees
25 Jun - 26 Jun
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather
Exterior

The Cabin Skowhegan

The Cabin Skowhegan
Skowhegan
9.8 out of 10, Exceptional, (53 reviews)
"Beautifully furnished cozy cabin and great hospitality from Larry and Lisa! Nice and toasty when we arrived and every detail was expertly crafted for a pleasant stay. Thank you so much for hosting our weekend in Skowhegan."
United States
Josh W.
The price is HK$784
HK$1,640 total
includes taxes & fees
13 Jul - 14 Jul
The Cabin Skowhegan
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

The Elmwood

The Elmwood

8/10 Good
"Basic, clean hotel. No frills, was as basic as it comes, good clean rooms, good beds, no loud guest or outside interference."
Dee 4-night trip
Posted 8 hours ago
The Elmwood

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. Our travellers also rate Pool, fire pit & minutes to Messalonskee Lake! 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 Kennebec Ice Arena, 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.