Oakland vacation rentals
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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
Apartment in Oakland
5.0 out of 5 average rating, 27 reviewsCentral Maine Loft Offering 4 Seasons of Fun
May 15 – 22
Cottage in Oakland
4.91 out of 5 average rating, 35 reviewsLakefront cottage in Belgrade Lakes
Oct 8 – 15
Home in Oakland
4.94 out of 5 average rating, 89 reviewsThe Modern Maine Retreat
Nov 5 – 12
Tiny home in Oakland
4.78 out of 5 average rating, 18 reviewsLavender Haze Cottage in Woods
Nov 29 – Dec 6
Home in Oakland
4.99 out of 5 average rating, 75 reviewsCall of the Loon-Snow Pond (Messalonskee Lake)
Oct 9 – 16
Apartment in Skowhegan
5.0 out of 5 average rating, 19 reviewsCute, new, modern duplex in renovated schoolhouse
Aug 16 – 23
Home in Oakland
4.88 out of 5 average rating, 85 reviewsLake-House on water, East Lake, Belgrade Lakes
Jun 2 – 9
Home in Fairfield
4.88 out of 5 average rating, 33 reviewsCozy home in Fairfield
Sep 1 – 8
Other great vacation rentals in Oakland
Guest suite in Hallowell
5.0 out of 5 average rating, 53 reviewsWelcome to the Brown House! Hallowell studio
Sep 7 – 14
Apartment in Skowhegan
4.93 out of 5 average rating, 14 reviewsUpstairs apartment
Dec 12 – 19
Guest suite in Chesterville
4.93 out of 5 average rating, 97 reviewsRustic Ridge
Aug 22 – 29
Home in Oakland
5.0 out of 5 average rating, 9 reviewsQuiet, 6 bedroom lakefront home with sandy beach
Dec 7 – 14
Cabin in Starks
4.88 out of 5 average rating, 58 reviewsPrivate tiny cabin on six acres of trees
Apr 7 – 14
Camper/RV in Fairfield
4.89 out of 5 average rating, 9 reviewsSpacious Camper
Jul 23 – 30
Cottage in Belgrade
4.82 out of 5 average rating, 22 reviewsCozy Cottage on Ellis Pond-Cabin #1 at Kozy Cove
Aug 22 – 29
Cottage in Belgrade
4.84 out of 5 average rating, 25 reviewsBelgrade Lakes Salmon Waterfront
May 19 – 26
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
€ 47 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 cottage rentals in Oakland?
Experience the best of Oakland with our cottage rentals, starting at about $110 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 house rentals in Oakland have wireless internet?
Absolutely! We offer over 20 house 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 a bbq area, over 10 homes with air conditioning, over 20 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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