Holiday rentals in Oakland

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Popular amenities for Oakland holiday rentals

Stay near Oakland's top sights

Colby College17 locals recommend
Colby Museum of Art45 locals recommend
Quarry Road Trails11 locals recommend
Buen Apetito9 locals recommend
Tree Spirits9 locals recommend
Belgrade Boat Shop6 locals recommend

Other great holiday rentals in Oakland

Superhost
Home in Carrabassett Valley
5 out of 5 average rating, 4 reviews

The Epic Sugarloaf Family Getaway!

KarenRating, 5 stars1 month ago
This place was very convenient to the mountain with a lift nearby and it was very clean and incredibly spacious. David is very accommodating and helpful. We sorely missed having coffee available in the morning but really that was our fault for not bringing it as it was not advertised that there would be any I just assumed for the price there would be a little coffee. Overall though great stay and very nice place - thank you!
Top guest favourite
Cottage in Belgrade
5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

SarahRating, 5 stars5 months ago
This property was awesome we were all very happy with the location, amenities, price and host. Hillary was polite and very helpful. This trip almost didn’t happen as our previous reservation was canceled 12 hours before check in from a different host. Luckily Hillary saved the week with her quick response time and answering questions about sleeping situations etc. would stay here again in a heart beat highly recommend!
Top guest favourite
Home in Gray
4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.
Guest favourite
Home in Dallas Plantation
4.93 out of 5 average rating, 29 reviews

Ski/snowmobile retreat-hot tub

HilaryRating, 5 stars1 month ago
This house is OUTSTANDING! The location is perfect, the house is spotlessly clean, top of the line kitchen. Our stay could not have been more perfect.
Superhost
Home in Hartland
5 out of 5 average rating, 3 reviews

The Great Moose in Stunning Maine Swim, Fish & Ka

KevinRating, 5 stars7 months ago
My kids and I had an amazing time during our Labor Day weekend stay. The neighbors were so friendly and nice. The house was beautiful and had everything we needed. A market nearby for quick things. Beautiful area, access to water was great. We even got to enjoy the Harmony Free Fair and fireworks! Great weekend thank you!
Guest favourite
Cabin in Moscow
4.95 out of 5 average rating, 92 reviews

Cabins/Sporting camps-great location

EricRating, 5 stars6 months ago
This is a gem of a place. Very close to where we wanted to bird hunt. Access to ATV trails (be respectful and drive slow on access/shared roads). All that you need is in this place. We stayed in Cabin #1. As she mentioned just bring a towel and toiletries. We ate out all the time. Breakfast and lunch at Bingham General Store. Dinner at Patrick’s Pub one night, next night at Kennebec River Brewing. We’ll be back for sure.
Top guest favourite
Home in Bath
5 out of 5 average rating, 101 reviews

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars1 month ago
The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.
Guest favourite
Cabin in Belgrade
5 out of 5 average rating, 7 reviews

Great Pond Getaway|Lakefront|Dock|Sunset Views

ElizabethRating, 5 stars7 months ago
Wonderful weekend stay w our adult children. Kitchen had everything we needed to make dinner. Views of the lake were stunning. We all enjoyed a swim and paddle in the kayaks.

Quick stats about holiday rentals in Oakland

  • Total rentals

    70 properties

  • Nightly prices starting at

    £38 before taxes and fees

  • Total number of reviews

    2.1K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Oakland