A lake surrounded by trees with autumn leaves.

Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (12 reviews)
"Very cute. Clean. Good location for an event at Bowl in the Pines."
United States
Lisa
The price is NZ$454
includes taxes & fees
16 Sept - 17 Sept
Sister A-Frame in Woods B

2. Central Maine Apartment offering 4 Seasons of Fun.

Central Maine Apartment offering 4 Seasons of Fun.
Oakland
10.0 out of 10, Exceptional, (48 reviews)
"Apartment was comfortable and as described. I had a nice stay."
United States
kathy e.
The price is NZ$462
includes taxes & fees
22 Sept - 23 Sept
Central Maine Apartment offering 4 Seasons of Fun.

3. The heart of the Belgrade Lakes

The heart of the Belgrade Lakes
Oakland
9.0 out of 10, Wonderful, (10 reviews)
"Host was very accommodating "
United States
Maureen
The price is NZ$404
includes taxes & fees
16 Sept - 17 Sept
The heart of the Belgrade Lakes

4. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (17 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is NZ$451
includes taxes & fees
20 Sept - 21 Sept
Discover Oakland charm near Colby College 10 min

5. 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, (16 reviews)
"Kathleen was a wonderful host. My family and I found the property welcoming and relaxing. Great place to stay if you are looking for a laid back atmosphere and peaceful time in the country."
United States
Jared
The price is NZ$652
includes taxes & fees
16 Sept - 17 Sept
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes

6. Private Dock on Messalonskee Lake: Cozy Cottage!

Private Dock on Messalonskee Lake: Cozy Cottage!
3.0 star property
Augusta
10.0 out of 10, Exceptional, (1 review)
"Great little lake cabin. Had everything we needed. Clean, comfortable, quite. Beautiful area and views. We had a wonderful stay and would stay again."
United States
John
The price is NZ$561
includes taxes & fees
16 Sept - 17 Sept
Private Dock on Messalonskee Lake: Cozy Cottage!

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, (56 reviews)
"Great place, quiet neighborhood off the lake, very comfortable. Would definitely stay again!"
United States
Steve C.
The price is NZ$558
includes taxes & fees
16 Sept - 17 Sept
Boat launch and Trailer parking, Dog Friendly, Lake Great Pond

8. 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, (3 reviews)
"WE were delighted in our accommodations. The apartment was lovely and very clean. Lynne was very responsive to my numerous questions. The location was centralized to hiking and biking trails and a quick jaunt to Augusta for the triathlon. I have to say that I slept like a baby too which is not a normal occurence for me. The mattress was so very comfortable. We would not hesitate to book here again. Thank you for a lovely visit."
United States
Cheri A.
The price is NZ$264
includes taxes & fees
16 Sept - 17 Sept
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine

9. 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 Host was great, I highly recommend this spot, everything was super smooth and the cabin was beautiful. "
United States
Jason B.
The price is NZ$297
includes taxes & fees
16 Sept - 17 Sept
Charming cabin in the birches right on the atv trail!

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is NZ$245
includes taxes & fees
27 Sept - 28 Sept
Fabulous 3-bedroom RV with direct access to the Sebasticook River!

11. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (26 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is NZ$439
includes taxes & fees
21 Sept - 22 Sept
Minutes to Colby

12. 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, (92 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
The price is NZ$436
includes taxes & fees
23 Sept - 24 Sept
Two bedroom Mid Century Modern apartment in Downtown Hallowell

13. Hammock Haven Island Dome

Hammock Haven Island Dome
Monmouth
9.4 out of 10, Exceptional, (6 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 NZ$260
includes taxes & fees
16 Sept - 17 Sept
Hammock Haven Island Dome

14. 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, (9 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is NZ$250
includes taxes & fees
23 Sept - 24 Sept
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

15. Pet-Friendly Island A-Frame w/ Lake Access

Pet-Friendly Island A-Frame w/ Lake Access
Monmouth
10.0 out of 10, Exceptional, (7 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 NZ$290
includes taxes & fees
20 Sept - 21 Sept
Pet-Friendly Island A-Frame w/ Lake Access

16. 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
9.8 out of 10, Exceptional, (46 reviews)
"Great experience"
United States
Chase D.
The price is NZ$594
includes taxes & fees
16 Sept - 17 Sept
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.

17. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (7 reviews)
"The property was lovely, and the host was wonderful!"
United States
Treseanne A.
The price is NZ$322
includes taxes & fees
27 Sept - 28 Sept
Cozy cottage in the Winthrop Lakes Area

18. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (2 reviews)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is NZ$301
includes taxes & fees
16 Sept - 17 Sept
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

19. Angel Mist Retreat Garage Apartment

Angel Mist Retreat Garage Apartment
Pittsfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay. Very comfortable, roomy, clean and good overall value."
United States
Rob K.
The price is NZ$523
includes taxes & fees
16 Sept - 17 Sept
Angel Mist Retreat Garage Apartment

20. Perfectly Located 1 Bedroom, newly remodeled

Perfectly Located 1 Bedroom, newly remodeled
Augusta
10.0 out of 10, Exceptional, (4 reviews)
"I’ve stayed in many rental properties and this one is by far the cleanest and nicest. Everything was exactly as described and there was even a second ac unit in the bedroom. It’s on a nice quiet street and convenient to many things. You truly can’t go wrong choosing to stay here."
United States
Lisa G.
The price is NZ$481
includes taxes & fees
16 Sept - 17 Sept
Perfectly Located 1 Bedroom, newly remodeled
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

Find out more about Oakland

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakland. Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakland short-term rentals, that won’t be hard to do.

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 Lakeview House with Deck, Cozy Fireplace and firepit as a favourite home for rent in Oakland.

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.