Oakland vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Oakland
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oakland vacation rentals
Other great vacation rentals in Oakland
Home in Oakland
5.0 out of 5 average rating, 54 reviewsCute 2-bedroom home in convenient central location
Nov 8 – 15
Home in Oakland
4.94 out of 5 average rating, 88 reviewsThe Modern Maine Retreat
May 3 – 10
Apartment in Oakland
5.0 out of 5 average rating, 27 reviewsCentral Maine Loft Offering 4 Seasons of Fun
May 2 – 9
Cottage in Oakland
4.91 out of 5 average rating, 33 reviewsLakefront cottage in Belgrade Lakes
Oct 13 – 20
Tiny home in Oakland
4.78 out of 5 average rating, 18 reviewsLavender Haze Cottage in Woods
Nov 3 – 10
Home in Oakland
4.99 out of 5 average rating, 75 reviewsCall of the Loon-Snow Pond (Messalonskee Lake)
May 6 – 13
Apartment in Skowhegan
5.0 out of 5 average rating, 18 reviewsCozy, cute, new, tiny duplex
Aug 4 – 11
Home in Fairfield
4.88 out of 5 average rating, 33 reviewsCozy home in Fairfield
May 6 – 13
Other great vacation rentals in Oakland
Apartment in Fayette
5.0 out of 5 average rating, 12 reviewsLimberlost East
Jul 14 – 21
Home in Oakland
5.0 out of 5 average rating, 14 reviewsPeaceful 5 bedroom 4.5 bath waterfront house
Jan 28 – Feb 4
Home in Starks
4.93 out of 5 average rating, 61 reviewsBeautiful Springtime Farm With Onsite Chef
Jan 1 – 8
Guest suite in Chesterville
4.93 out of 5 average rating, 97 reviewsRustic Ridge
Aug 17 – 24
Home in Oakland
4.88 out of 5 average rating, 85 reviewsLake-House on water, East Lake, Belgrade Lakes
Sep 13 – 20
Home in Oakland
4.93 out of 5 average rating, 57 reviewsClassy AF Home Steps from Colby and Trails
Sep 24 – Oct 1
Home in Waterville
4.92 out of 5 average rating, 87 reviewsSterling House
Sep 2 – 9
Apartment in Unity
4.98 out of 5 average rating, 42 reviewsThe Heron's Nest Cozy apartment in the woods.
Nov 17 – 24
Quick stats about vacation rentals in Oakland
Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$50 before taxes and fees
Frequently Asked Questions
Are there pet-friendly vacation rentals in Oakland?
Four-legged friends are welcome in Oakland. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Oakland?
Yes! Work meets play with ease at over 20 vacation rentals in Oakland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Oakland?
Oakland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oakland?
Experience the best of Oakland with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oakland have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Oakland. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Oakland have wireless internet?
Absolutely! We offer over 10 cottage rentals with wireless internet in Oakland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oakland have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Oakland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oakland?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with wireless internet, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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