House vacation rentals in Oakland
Find and book unique houses on Airbnb
Top-rated house rentals in Oakland
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Turner
4.84 out of 5 average rating, 70 reviewsThe Getaway- River Paradise
every thing was great. I had to get in touch with David when we first arrived and he got back to me immediately. Everybody like it. We will certainly get in touch with David when we come back to Maine. The only thing I would do If I were David is put the house numbers on the mailbox, we were concerned we were going to the right house but really no problem
Home in Liberty
4.87 out of 5 average rating, 55 reviewsLuxe Liberty: Getaway with Heated Indoor Pool!
Our family gathered at Rebecca's place for our holiday celebration. The home provided a fantastic array of things to do and spaces in which to gather together. We loved the swimming pool, the pool table, and puzzle-making! Great place for a gathering or celebration. Rebecca was incredibly timely with responses to any questions we had, and most accommodating with some last minute requests.
Home in Carrabassett Valley
4.75 out of 5 average rating, 12 reviews*New to Market* 410 Snowflower
Great stay and quick response from the owner. Perfect location for lots of activities and restaurants. I would highly recommend.
Home in Mechanic Falls
5 out of 5 average rating, 19 reviewsLovely home with hot tub and pool
Beautiful Airbnb! Everything in the Airbnb was very well thought out. The host was super nice and always quick to respond. My only regret was not spending more time here!
Home in Rockport
4.96 out of 5 average rating, 52 reviewsDog Friendly Midcoast Cape
BEAUTIFUL Home!! Tons of space to relax and spread out with our family! The beds were very comfortable! We really appreciated all of the bathrooms for our group! The kitchen was huge and so handy for preparing meals! I absolutely loved the style and atmosphere of this wonderful home! We also loved being able to bring our dogs!! We had a lovely time and we would most definitely come back!!! 🥰
Home in Windham
4.73 out of 5 average rating, 11 reviewsGorgeous Maine House Close to Sebago Lake
This was our second stay at Craig's place. It is a perfect home for our two families which include a 2, 4, and 14 year olds. there is plenty of space and the pool area and indoor basketball gym are such an amazing treat! We were happily surprised to find a new mini split in the large game room which cooled the whole downstairs.
Home in Carrabassett Valley
4.83 out of 5 average rating, 64 reviewsSUGARLOAF, TRAILSIDE, 4-BDRM, & AC
Peaceful and quiet. Went to Sugarloaf Resort for a conference for the week. The condo was 2-minute drive. took in sights of the surrounding area. Nice motorcycle riding roads
Home in Dresden
5 out of 5 average rating, 10 reviewsWild Grace Spa
Well, usually I don't write the reviews my wife does a better job than I, but we were only staying two nights, and we were out and about a lot, only regret is time didn't allow for us to use the offerings / amenities that Emily offers, it all looked so inviting! we will be back, and we will plan our time accordingly to utilize what Emilys place offers. thx again Emily!
Weekly house rentals
Home in Brunswick
4.85 out of 5 average rating, 119 reviewsKing beds-Charming Retro 3BR+Office House
This was our first experience with an Air B&B and happy that it was with Spencer. Our main reason for the East Coast trip was to see our grandsons football games at Bowdoin College and it was a perfect location. We stayed for seven weeks and loved the experience.
Home in Waterville
4.92 out of 5 average rating, 121 reviewsSterling House
Cute little place in a quiet residential neighborhood. House was clean, nice bed linens, nice hot shower with lots of towels. If I have any criticisms I’d say the bathroom vanity is a bit too small, and the upper kitchen cabinets are higher than standard, so were a stretch for us to reach even the bottom shelves for dishes, etc. But all told, a descent place and I would not hesitate to stay here again.
Home in Rangeley
4.8 out of 5 average rating, 54 reviewsSnowmobile SKi ATV in Rangeley 3 bedroom home
We’ve stayed here before and enjoy the space and location. Great place to stay for the price. Host is always responsive and friendly.
Home in Belfast
4.9 out of 5 average rating, 147 reviewsYellow Door - One Floor Living Close to Downtown!
Had an amazing stay at Judith’s place! The location is perfect, super close to town and walking distance to the grocery store. She gave us great recommendations for restaurants and was very responsive! If we come back to Belfast, we will definitely stay here again!
Home in Newcastle
4.96 out of 5 average rating, 45 reviewsCozy & quiet on the river... the Captain's House
The hosts were very prompt in communicating. The thoughtfulness they have put into furnishing the property is amazing. It has a very vintage nautical feeling to it. The house is extremely well appointed. We didn’t have any problems at all. The surroundings are off the beaten path which we especially appreciated. It’s a short 10 minute drive to Damariscotta Downtown. I would highly recommend this property.
Home in Dallas Plantation
4.83 out of 5 average rating, 6 reviewsSaddleback Lake Lodge AFrame | Close to Saddleback
The exterior photo didn’t exactly do justice to the house, the A frame is not a beautiful profile but the house is sturdy, attractive, spacious, cozy and clean. Had everything we needed. Beautiful place, Saddleback Lake Lodge!
Home in Naples
4.67 out of 5 average rating, 12 reviewsPinecrest Lakefront, Private 1 Bedroom
Only stayed for one night but it was beautiful very inviting. Cozy with the fireplace and gorgeous Christmas tree. We arrived in the dark so it was wonderful to wake up to the amazing view from the house. Scott was a great host. Will definitely be back
Home in Camden
4.93 out of 5 average rating, 130 reviewsCozy Cottage With River View
We really enjoyed our stay at Jeremy's cottage! The home is charming, cozy, and very well-appointed, with everything we needed – plenty of linens, kitchen supplies, cutlery, and more. The back porch overlooking the river or the breakfast nook were perfect spots for morning coffee, and the kitchen made it easy to cook meals with lots of space. The bedrooms were comfortable and made for a restful night's sleep. The location is fantastic too! Short walk into Camden for great food or shops but also centrally located to visit nearby by towns like Lincolnville, Rockport, and Rockland. Jeremy was a terrific host – friendly, responsive, and helpful. I left my yoga mat behind and he was kind enough to offer to ship back to me. We thoroughly enjoyed our time in Camden and would definitely recommend this cottage!
Private house rentals
Home in Belfast
5 out of 5 average rating, 33 reviewsIn-town, 1870’s Spacious Home
We cannot say enough wonderful things about this lovely property. Lee and Charlie were so fantastic to work with, and the home was spacious, fully stocked and beautifully decorated. We would definitely come back and highly recommend it! Communication was terrific!
Home in Bristol
5 out of 5 average rating, 30 reviewsOcean-side home on 24 acres (w/ EV+Tesla charger)
This is an amazing property with a very cool house. Check-in was easy, Tyler is a very responsive host, and we were able to find everything we needed and wanted. We especially enjoyed the wood-fired sauna during sunrise, and the fire pit in the evenings.
Home in Auburn
4.88 out of 5 average rating, 74 reviewsScandinavian Lakehouse - King Bed - Pet friendly
This lake house was absolutely perfect! Comfortable, clean, and thoughtfully maintained, it felt like a true home away from home. The house was fully stocked with all the supplies we could possibly need, making the stay incredibly convenient and stress-free. The peaceful setting, paired with its unbeatable location, made it an exceptional getaway. We loved how everything was designed to ensure a relaxing and seamless experience. Can’t wait to come back and stay here again—it was everything we hoped for and more! Top notch.
Home in Belfast
5 out of 5 average rating, 11 reviews4bed Full House on Private Dr. w/ Large Yard
Our family was able to come together to relax, cook, enjoy Belfast and celebrate our own little Christmas. We were super comfortable and really enjoyed the space. The house had everything we needed!
Home in Naples
4.99 out of 5 average rating, 98 reviewsLUX Designer Private Waterfront
What a beautiful weekend getaway! We loved how cozy this home was. Jon was very responsive and helpful for getting us everything we needed during our stay. Definitely recommend this home for anyone looking for a nice private retreat. We stayed in the winter, but I'm sure it's great any time of year!
Home in Belgrade
4.92 out of 5 average rating, 13 reviews5Bed- Hot Tub - Sauna-Pool Table -Lake Front, Pets
Chris and Alanna have an incredible property. The house is large, but at the same time very cozy. It's great for entertaining guests. The beds are incredibly comfortable, and the heat pumps are fantastic. Being right on the water with 600' of sandy frontage was amazing. It was incredibly simple to use the mooring for the boat we rented as well. I can't say enough positive things about the property, and that goes the same for the owners. They have to be the best hosts we've ever found through a vacation service. They were responsive, friendly, helpful, and really just always wanting to go above and beyond to make sure my family had the best vacation ever. We will intend on going back for many years, it was a dream!
Home in Cushing
4.97 out of 5 average rating, 29 reviewsMaine-Coast Reunions & Retreats: Studio/Dock/Pets
We stayed at Jonathan’s place for my bachelorette trip to Maine and it was absolutely perfect for a quiet ladies weekend with beautiful surroundings. The house had nearly everything we needed, and everything we weren’t able to bring or find at the house could easily be purchased at the nearby Fales Store that Jonathan recommended. The kitchen was impressively well-stocked and we had more than enough blankets, towels, etc. to accommodate 11 women. Jonathan’s place provided a halfway point between Portland and Acadia National Park where we spent part of our weekend in peak fall color. It’s also a short 30min drive from Camden Harbor where we chartered a sailboat before coming back to a cozy fire in the wood burning fireplace and a gas firepit in the backyard. The house had plenty of space for all of us to sleep and to socialize. Jonathan was very responsive at check-in and check-out. We felt so welcome - 10/10 would recommend, we had an incredible weekend!
Home in Cornville
4.94 out of 5 average rating, 36 reviewsHilltop Rentals LLC-Tranquil Country Home in Maine
Great host, beautiful home full of interesting antiques. Loved the library. Very warm and cozy place to stay. Very neat and clean.
Quick stats about house rentals in Oakland
Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Portland Vacation rentals
- Bar Harbor Vacation rentals
- Old Orchard Beach Vacation rentals
- Bangor Vacation rentals
- China Vacation rentals
- Acadia National Park Pond Vacation rentals
- Montreal Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Cape Cod Vacation rentals
- Québec Vacation rentals
- Québec City Vacation rentals
- Guesthouse rentals United States
- Earth house rentals United States
- Lighthouse rentals United States
- Townhouse rentals United States
- House rentals United States
- Lakehouse rentals Maine
- Beach house rentals Maine
- Treehouse rentals Maine
- Guesthouse rentals Maine
- Tiny house rentals Maine
- Townhouse rentals Maine
- House rentals Maine
- Townhouse rentals Portland
- Beach house rentals Portland
- House rentals Portland
- House rentals Bar Harbor
- Townhouse rentals Bar Harbor
- Guesthouse rentals Bar Harbor
- Pet-friendly rentals Oakland
- Rentals with a washer and dryer Oakland
- Monthly Rentals Oakland
- Rentals with outdoor seating Oakland
- Rentals with a kayak Oakland
- Rentals with lake access Oakland
- Rentals with a fireplace Oakland
- Rentals with a fire pit Oakland
- Rentals with a patio Oakland
- Family-friendly rentals Oakland
- Waterfront rentals Oakland
- Kid-friendly rentals Oakland
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes