A lake surrounded by trees with autumn leaves.

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Oakland vacation rentals

Exterior

Sister A-Frame in Woods B

Sister A-Frame in Woods B
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"Great stay. Would stay here again if in the area."
United States
Amanda M.
The price is AED 443
AED 951 total
includes taxes & fees
15 Jul - 16 Jul
Sister A-Frame in Woods B
Exterior

Discover Oakland charm near Colby College 10 min

Discover Oakland charm near Colby College 10 min
Oakland
9.8 out of 10, Exceptional, (13 reviews)
"Very clean and comfy. A pleasure to stay there. "
United States
Vicki W.
The price is AED 371
AED 773 total
includes taxes & fees
29 Jul - 30 Jul
Discover Oakland charm near Colby College 10 min
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 AED 422
AED 869 total
includes taxes & fees
12 Jul - 13 Jul
The heart of the Belgrade Lakes
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, (48 reviews)
"Fantastic quiet location and beautiful property.Everything you could possibly need has been supplied and the property is absolutely spotless.The hosts communicated perfectly, including facilitating an extremely late check-in.We would highly recommend this property - and we are hoping to return in the summer.Thank you for a wonderful stay!"
United States
Stephen R.
Central Maine Apartment offering 4 Seasons of Fun.
Outdoor dining

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
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 AED 1,138
AED 1,824 total
includes taxes & fees
2 Aug - 3 Aug
Peaceful retreat on farm minutes to lake. Bring kayak or canoe!
Miscellaneous

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

Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Benton
The price is AED 281
AED 466 total
includes taxes & fees
16 Jul - 17 Jul
Fabulous 3-bedroom RV with direct access to the Sebasticook River!
Smart TV

Charming cabin in the birches right on the atv trail!

Charming cabin in the birches right on the atv trail!
Fairfield
9.2 out of 10, Wonderful, (7 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 314
AED 522 total
includes taxes & fees
5 Jul - 6 Jul
Charming cabin in the birches right on the atv trail!
WiFi, bed sheets

The StarGazer Floating Dome

The StarGazer Floating Dome
Monmouth
The price is AED 300
AED 827 total
includes taxes & fees
8 Jul - 9 Jul
The StarGazer Floating Dome
Exterior

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

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
Madison
9.2 out of 10, Wonderful, (5 reviews)
"Excellent service and perfect for our stay. Would book again!"
United States
Scott
The price is AED 466
AED 588 total
includes taxes & fees
7 Jul - 8 Jul
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine
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 AED 496
AED 621 total
includes taxes & fees
14 Jul - 15 Jul
Paddle, float, fish, or rope swing into the lake. Direct ATV trail access too!
Exterior

Wilson Lake Inn

Wilson Lake Inn
3.0 star property
Wilton
The price is AED 572
AED 623 total
includes taxes & fees
9 Jul - 10 Jul
Wilson Lake Inn
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 AED 547
AED 1,349 total
includes taxes & fees
15 Jul - 16 Jul
Cabin,30 acres, privacy, Fire pit, picnic table, BBQ, trails & close to town.
Cottage (2 Bedrooms) | Front of property

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 540
AED 1,323 total
includes taxes & fees
29 Jul - 30 Jul
Private Dock on Messalonskee Lake: Cozy Cottage!
Fridge, microwave, oven, stovetop

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
The price is AED 551
AED 685 total
includes taxes & fees
5 Jul - 6 Jul
Whitsendsport unit 4 1 bedroom & queen pull out couch on 50 acres Smithfield
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, (7 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 AED 621
AED 969 total
includes taxes & fees
5 Jul - 6 Jul
Cabin Style Studio Apt with Private Hot tub on 100 Acres Kayaks, Canoes & SUP
Interior

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

River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
Hallowell
The price is AED 519
AED 650 total
includes taxes & fees
6 Jul - 7 Jul
River View Retreat, Hot Tub, Balcony, Kayaks & Bikes
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 AED 516
AED 1,131 total
includes taxes & fees
11 Jul - 12 Jul
Angel Mist Retreat Garage Apartment
Terrace/patio

The Beach Bum | Modern Cabin on the Sand

The Beach Bum | Modern Cabin on the Sand
Burnham
10.0 out of 10, Exceptional, (2 reviews)
"Nice cottage. Perfect location. Everything you need for a quiet beach stay on Unity pond. "
United States
Albert
The price is AED 933
AED 1,899 total
includes taxes & fees
6 Jul - 7 Jul
The Beach Bum | Modern Cabin on the Sand
Interior

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
The price is AED 654
AED 1,145 total
includes taxes & fees
7 Jul - 8 Jul
Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters
Paper towels

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
10.0 out of 10, Exceptional, (1 review)
"Clean and new."
United States
erik s.
The price is AED 551
AED 685 total
includes taxes & fees
5 Jul - 6 Jul
Cozy new 1 bedroom, queen bed, and queen sofa bed, washer/dryers. Radiant heat.
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

Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

10/10 Excellent
"The room was clean. The staff was friendly."
Brian 1-night trip
Posted 12 hours ago
Fireside Inn & Suites Waterville

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?

Peaceful retreat on farm minutes to lake. Bring kayak or canoe!: This Oakland vacation home rental is located in a rural location and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Cozy Long Pond Cottage: community access, private mooring & shared dock. as a favorite home for rent in Oakland.

How many vacation rentals will I find in Oakland?

Choose from 35 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. Tree Spirits and East Pond 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.