A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Oakland vacation rentals

Exterior

1. Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (10 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 443
AED 959 total
includes taxes & fees
24 Aug - 25 Aug
Sister A-Frame in Woods B
2 bedrooms, WiFi, bed sheets

2. 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 AED 422
AED 865 total
includes taxes & fees
24 Aug - 25 Aug
The heart of the Belgrade Lakes
Exterior

3. Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (15 reviews)
"House very clean and convenient location for what we had going on. "
United States
Tammy W.
The price is AED 518
AED 965 total
includes taxes & fees
20 Sep - 21 Sep
Discover Oakland charm near Colby College 10 min
Outdoor dining

4. 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 AED 868
AED 1,717 total
includes taxes & fees
2 Sep - 3 Sep
Fall Getaway at My Valhalla Farm- close to Waterville and minutes to lakes
Living area

5. Amazing Lake House On Great Pond! Stunning Sunsets & Renovated Bunkhouse Bar

Amazing Lake House On Great Pond! Stunning Sunsets & Renovated Bunkhouse Bar
Belgrade
The price is AED 1,286
AED 1,593 total
includes taxes & fees
7 Sep - 8 Sep
Amazing Lake House On Great Pond! Stunning Sunsets & Renovated Bunkhouse Bar
Smart TV

6. 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 AED 413
AED 631 total
includes taxes & fees
1 Sep - 2 Sep
Charming cabin in the birches right on the atv trail!
Paper towels

7. 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, (2 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 AED 477
AED 601 total
includes taxes & fees
31 Aug - 1 Sep
Cozy newly built 1-bedroom unit 2 Kentucky Bay in charming Smithfield Maine
Cottage (2 Bedrooms) | Front of property

8. 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 AED 419
AED 1,191 total
includes taxes & fees
16 Sep - 17 Sep
Private Dock on Messalonskee Lake: Cozy Cottage!
Outdoor dining

9. Minutes to Colby

Minutes to Colby
Waterville
8.8 out of 10, Excellent, (25 reviews)
"Close to our event, great communication, clean, comfortable & cozy"
United States
Shelly B.
The price is AED 584
AED 933 total
includes taxes & fees
2 Sep - 3 Sep
Minutes to Colby
Interior

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful camper and property! We loved it!"
United States
Tracy D.
The price is AED 331
AED 520 total
includes taxes & fees
26 Aug - 27 Aug
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Living area

11. Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath

Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
Smithfield
The price is AED 551
AED 689 total
includes taxes & fees
2 Sep - 3 Sep
Country setting close to lake 1 bedroom queen bed sofa, full kitchens and bath
TV

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, (91 reviews)
"House and community was amazing love the vibe of house experience was far and above expectations "
United States
Mike W.
The price is AED 433
AED 849 total
includes taxes & fees
2 Sep - 3 Sep
Two bedroom Mid Century Modern apartment in Downtown Hallowell
Exterior

13. 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, (8 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is AED 413
AED 530 total
includes taxes & fees
30 Aug - 31 Aug
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Interior

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
10.0 out of 10, Exceptional, (1 review)
"Great place and great host. Right in the water and close to New York and Canada"
United States
Anthony R.
The price is AED 522
AED 653 total
includes taxes & fees
31 Aug - 1 Sep
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Property grounds

15. The Love Nest - a Cozy Lakefront Log Cabin

The Love Nest - a Cozy Lakefront Log Cabin
Farmington,
9.6 out of 10, Exceptional, (8 reviews)
"One-of-a-kind Nirvana If you are looking for peace beauty simplicity a d restoration at a soul level look no further. Everything you need and nothing you don't. Host, cabin, setting, amenities all superb. Thank you beyond words! "
United States
Tracy Ann L.
The Love Nest - a Cozy Lakefront Log Cabin
Exterior

16. 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 AED 516
AED 1,147 total
includes taxes & fees
24 Aug - 25 Aug
Angel Mist Retreat Garage Apartment
Terrace/patio

17. Cozy cottage in the Winthrop Lakes Area

Cozy cottage in the Winthrop Lakes Area
Winthrop
9.8 out of 10, Exceptional, (7 reviews)
"My only regret is that we were only there for one night & didn’t have time to enjoy the surroundings."
United States
Nicole B.
The price is AED 382
AED 685 total
includes taxes & fees
31 Aug - 1 Sep
Cozy cottage in the Winthrop Lakes Area
Exterior

18. 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 AED 588
AED 1,029 total
includes taxes & fees
25 Aug - 26 Aug
Perfectly Located 1 Bedroom, newly remodeled
Property grounds

19. 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)
"Great experience"
United States
Chase D.
The price is AED 547
AED 1,369 total
includes taxes & fees
3 Sep - 4 Sep
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Interior

20. 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 AED 661
AED 1,169 total
includes taxes & fees
31 Aug - 1 Sep
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
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
"Gorgeous place staff is beyond awesome! We love it here!!"
Rachel 1-night trip
Posted 7 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, there are vacation rentals close to popular sights in Oakland, or you can go with a secluded option if you want a relaxing place to 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 vacation rentals in Oakland?

Cozy Long Pond Cottage: community access, private mooring & shared dock.: This Oakland vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate Charming Lakeview House with Deck, Cozy Fireplace and firepit as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 32 Expedia vacation rentals in Oakland for a memorable vacation.

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. Great Pond and Tree Spirits are other places to visit while you're in town.

What are vacation rentals like in Oakland?

Vacation rentals are private accommodations you can stay in for several days or more in Oakland. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family gatherings.