A lake surrounded by trees with autumn leaves.

Oakland Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Oakland holiday rentals

A wooden cabin with a porch, a door, and a green chair.

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (13 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is HK$706
HK$1,667 total
includes taxes & fees
10 Nov - 11 Nov
Sister A-Frame in Woods B
A wooden deck with outdoor furniture, a large potted plant, and string lights.

2. Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Oakland
10.0 out of 10, Exceptional, (18 reviews)
"We loved staying at the farm! My kids enjoyed meeting the horse and donkey on property. It was perfect for our family!"
United States
Shana S.
The price is HK$1,854
HK$2,174 total
includes taxes & fees
6 Nov - 7 Nov
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Property grounds

3. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (50 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is HK$816
HK$1,856 total
includes taxes & fees
8 Nov - 9 Nov
Central Maine Apartment offering 4 Seasons of Fun.
A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

4. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.2 out of 10, Wonderful, (11 reviews)
"Host was very accommodating "
United States
Maureen
The price is HK$902
HK$1,753 total
includes taxes & fees
19 Nov - 20 Nov
The heart of the Belgrade Lakes
A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

5. Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.
Waterville
9.6 out of 10, Exceptional, (65 reviews)
"Clean and Cozy! Always perfect for our stay "
United States
Rebecca B.
The price is HK$1,161
HK$1,898 total
includes taxes & fees
8 Nov - 9 Nov
Cozy House in the heart of Waterville Maine.
A modern kitchen with a black refrigerator, dark cabinets, and a wooden dining table with a bench.

6. Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Smithfield
10.0 out of 10, Exceptional, (4 reviews)
"A lovely spot. It is extremely clean. The hostess has thought of everything! There are plenty of nice towels and facecloths and bedding. The bed is very comfortable. We have enjoyed our stay"
Canada
Sherrie
The price is HK$941
HK$1,129 total
includes taxes & fees
19 Nov - 20 Nov
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
A room with a sliding glass door leading to a deck, a wooden table, and a chair.

7. 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, (58 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is HK$1,198
HK$2,877 total
includes taxes & fees
9 Nov - 10 Nov
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond
A modern RV kitchen with a built-in stove, sink, and refrigerator, a seating area, and a large window.

8. Fabulous 3-bedroom RV with direct access to the Sebasticook River!

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.6 out of 10, Exceptional, (8 reviews)
"Everything was so clean and nice!! Beautiful spot! Had everything we needed for our stay! Host was responsive to questions. Would come again for sure!!!"
United States
Hannah
The price is HK$600
HK$928 total
includes taxes & fees
30 Nov - 1 Dec
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

9. 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, (96 reviews)
"Cute place, quiet neighborhood close to downtown."
United States
Melissa F.
The price is HK$883
HK$1,681 total
includes taxes & fees
8 Nov - 9 Nov
Two bedroom Mid Century Modern apartment in Downtown Hallowell
A modern kitchen with dark cabinets, a black refrigerator, and a wooden dining table with bar stools.

10. Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield

Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
Smithfield
8.0 out of 10, Very good, (1 review)
"Very clean and centrally located for the Belgrade Lakes. Nice people and I will definitely stay again."
United States
Mike F.
The price is HK$941
HK$1,129 total
includes taxes & fees
19 Nov - 20 Nov
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
A spacious living area with a large wooden dining table, a built-in kitchen island, and a view of the outdoors through large windows.

11. A soul soothing escape. Artistically built and lovingly maintained.

A soul soothing escape. Artistically built and lovingly maintained.
New Sharon
10.0 out of 10, Exceptional, (31 reviews)
"Loved the cabin and the view!! Had a great stay, thank you to our host!! Would love to stay again "
United States
Matt W.
The price is HK$2,013
HK$3,160 total
includes taxes & fees
14 Nov - 15 Nov
A soul soothing escape. Artistically built and lovingly maintained.
A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

12. 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
9.0 out of 10, Wonderful, (4 reviews)
"Very nice property, great location, nice decor, pet friendly, and good kitchen area."
United States
Laura M.
The price is HK$1,373
HK$2,318 total
includes taxes & fees
6 Nov - 7 Nov
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
A cozy cabin interior with a wooden floor, a sofa, a table, and a television mounted on the wall.

13. Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
8.6 out of 10, Excellent, (9 reviews)
"The cabin was perfect for our two night stay. It was very clean and it felt just like being at home. Misty was a responsive host and I would definitely rent here again."
United States
Tonilynne D.
The price is HK$745
HK$1,069 total
includes taxes & fees
5 Dec - 6 Dec
Charming cabin in the birches right on the atv trail!
A stone fire pit with a red Adirondack chair and a picnic table with a striped umbrella in a grassy outdoor area.

14. 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, (45 reviews)
"Really neat cabin that has been added onto. The backstory was really cool to read. Highly recommend this cabin. Extremely peaceful and private. Highly recommend this host and staying here!"
United States
Blake B.
The price is HK$1,052
HK$2,515 total
includes taxes & fees
3 Dec - 4 Dec
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
A modern kitchen with dark blue cabinets, a black refrigerator, and a wooden table with black cushioned benches.

15. Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.

Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
Smithfield
9.4 out of 10, Exceptional, (3 reviews)
"The stay was nice, it was cute place and priced reasonably. The horses across the street were a fun surprise in the morning."
United States
Hailey M.
The price is HK$941
HK$1,129 total
includes taxes & fees
19 Nov - 20 Nov
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
A modern building with a black exterior and a large glass entrance.

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.4 out of 10, Exceptional, (10 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is HK$1,024
HK$1,159 total
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

17. China Lake, Dog Friendly, Lots of space for family gatherings

China Lake, Dog Friendly, Lots of space for family gatherings
China
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for family gatherings Home was very clean and well stocked Host responded quickly to all messages Love that it is pet friendly"
United States
Anne S.
The price is HK$1,809
HK$4,896 total
includes taxes & fees
8 Nov - 9 Nov
China Lake, Dog Friendly, Lots of space for family gatherings
A covered porch with wicker furniture, a white door, and a welcome mat.

18. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (9 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
The price is HK$816
HK$1,377 total
includes taxes & fees
12 Nov - 13 Nov
Cozy cottage in the Winthrop Lakes Area
A large, red, two-story house with a balcony and a tower, surrounded by a fence and trees.

19. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Very quiet and lovely apartment. The host was very accommodating and attentive to my questions."
United States
Ruth W.
The price is HK$1,101
HK$2,312 total
includes taxes & fees
7 Nov - 8 Nov
Angel Mist Retreat Garage Apartment
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
"The hotel was clean breakfast was excellent the location was super convenient to my son’s college and the rooms were very clean"
David 2-night trip
Posted 1 day 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
  • 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?

Stunning Belgrade Lakes Waterfront Retreat – Dock, Kayaks & Breathtaking Views!: This highly rated holiday home rental in Oakland offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Some other top choices in Oakland are Cozy Long Pond Cottage: community access, private mooring & shared dock. and Charming Lakeview House with Deck, Cozy Fireplace and firepit.

How many holiday rentals will I find in Oakland?

Choose from 31 Expedia holiday rentals in Oakland for a memorable holiday.

What can I see and do in Oakland?

Belgrade Lakes Chain and Messalonskee Lake are a couple of lovely local spots to get outside and enjoy nature. East Pond and Great Pond are other places to visit while you're in town.

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.