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Compare 125 Vacation Homes in Oakland with updated reviews, rates, and availability.

Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
View of house from lake
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
10.0 out of 10, Exceptional, (236)
"Had a nice quiet getaway here in the off-season. Enjoyed the hot tub and peace and quiet looking out on the lake. Very spacious and as advertised. Dog friendly for our small dog. Easy to check-in/out. Would definitely consider again if we were coming up to this area."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Avoid steep stairs that tire you out, our grounds slope gently to the lake!
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
10.0 out of 10, Exceptional, (14)
"Awesome"
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
9.0 out of 10, Wonderful, (4)
"We hosted a clinic and brought staff up from across the country. All the hotels were sold out so we rented the house. The staff now told us they don’t ever want to stay at the hotel again. This house all the way!"
The Three Cornered Pond Retreat | House in Augusta with kayaks & dock access
Charming Wilton Vacation Rental w/ Fire Pit
Wilton Vacation Rental | 4BR | 2BA | 2,300 Sq Ft | 2 Steps to Enter
Charming Wilton Vacation Rental w/ Fire Pit
10.0 out of 10, Exceptional, (4)
"This was an excellent rental property and we had a lovely stay here. The house was exactly as described and very well furnished. It was a comfortable place to the relax for the weekend and a very easy place to stay with dogs. I’d happily stay here again."
Charming Wilton Vacation Rental w/ Fire Pit
Veedon Fleece on the Lake
Exterior
Veedon Fleece on the Lake
10.0 out of 10, Exceptional, (14)
"Really nice stay. Area is beautiful. Right on the water. Excellent communication with the owner. A little dated and sitting room furniture is quite uncomfortable for sitting around and visiting. But overall a nice place to stay. "
Veedon Fleece on the Lake
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.0 out of 10, Very Good, (15)
"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
9.0 out of 10, Wonderful, (18)
"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."
Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK
Lakefront, Stunning Home only 30 min to Sugarloaf!
Living Room with Electric Fireplace
Lakefront, Stunning Home only 30 min to Sugarloaf!
10.0 out of 10, Exceptional, (25)
"Beautiful peaceful spot on the pond/lake. We could not have enjoyed our stay more! Clean, well equipped and tremendous view of the pond and mountains. We are already discussing going back next year. Special place!"
Lakefront, Stunning Home only 30 min to Sugarloaf!
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
Exterior
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
10.0 out of 10, Exceptional, (56)
"Super cozy place. Use a silver popper on the pond"
Light-Filled Log Home, 4 Wooded Acres, & Lake Access. The water is 0.4 mi away.
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Exterior
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
10.0 out of 10, Exceptional, (4)
"The house had a lot of room. This would be a great family getaway place. The host was available and very attentive. I would recommend this house. "
5BED HOUSE-HOT TUB, SAUNA, POOL TABLE, FIRE PIT, 3+ LG TV, PRIVATE LAKE FRONTAGE
Cozy Long Pond Cottage: private mooring & shared dock
Come enjoy this warm cottage!
Cozy Long Pond Cottage: private mooring & shared dock
9.8 out of 10, Exceptional, (8)
"The stay was a very nice place and we will be coming back with the whole family next time. "
Cozy Long Pond Cottage: private mooring & shared dock
Lovely dog-friendly lakefront abode with firepit, swimming dock, and fast WiFi
Lovely dog-friendly lakefront abode with firepit, swimming dock, and fast WiFi
8.8 out of 10, Excellent, (13)
"The place was cool, nice and clean. The place was a safe neighborhood, the places of interest are just nearby. I love to be back again. Thanks for the lovely experienced."
Lovely dog-friendly lakefront abode with firepit, swimming dock, and fast WiFi
Find Your Bliss at this Private and Captivating Lakeside Retreat
Exterior
Find Your Bliss at this Private and Captivating Lakeside Retreat
10.0 out of 10, Exceptional, (19)
"This place was great! Large, private, right on the water. Filled with nature vibes. We had a larger group and felt there was plenty of space- Dan the property manager was super helpful! "
Find Your Bliss at this Private and Captivating Lakeside Retreat
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]
Property grounds
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]
10.0 out of 10, Exceptional, (42)
"Second year at this home. Will exceed all expectations. Water access, scenery, privacy, comfort, etc."
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Exterior
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
10.0 out of 10, Exceptional, (27)
"Booked this cozy home in New Vineyard because it was close to the areas we wanted to visit. Perfect stay. Great communication with hosts, clear instructions. Home was spotless, comfortable, warm and well stocked with everything we needed to enjoy a cup of coffee & tea and cook meals. Also enjoyed the fire pit and making smores! Because this house sits a little higher than the others nearby, it gives a great view to all the beautiful fall foliage all around. Another bonus is it is very close...
Peaceful, Cozy Getaway - Near Skiing, fishing, snowmobiling, ATV, UMF, FMH
Charming Historic Lakefront Home w/ Expansive Porches, Kayaks & Spacious Living!
Exterior
Charming Historic Lakefront Home w/ Expansive Porches, Kayaks & Spacious Living!
9.4 out of 10, Exceptional, (3)
"This home is spacious with an antique charm. It offers all the amenities you need. You can enjoy a coffee on the large porch at sunrise while overlooking the water. Or, maybe kayak throughout the day. Our visit was a short stay and this home provided enough for what we needed. "
Charming Historic Lakefront Home w/ Expansive Porches, Kayaks & Spacious Living!
Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula
Exterior
Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula
9.2 out of 10, Wonderful, (16)
"Our family had a great time at the Chin's Lake House. The house inside was modern, the outside rustic which made it interesting. Inside the house it was fairly clean. We did need to go though 2 cabinets and bag food as it was left opened. This made us uncomfortable as there are a lot of ants in critters on the property. Otherwise the rest of the house was clean. The outside is rustic and in need of TLC but a typical Lake house with wear and tear. The Lake and dock were perfect as we are outdoor...
Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Sunrise on the lake
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
9.6 out of 10, Exceptional, (64)
"There for project in the area .. accommodations were all as advertised .. old school camp feel with all the modern amenities .. well appointed with a local flair .. would recommend to all …"
Lake Front House ~ Fire pit ~ Canoes/Kayaks ~ Large Deck ~Grill - Secluded Beach
Lake Front with Amazing Sunsets on McGrath Pond
Enjoy beautiful sunsets every night.
Lake Front with Amazing Sunsets on McGrath Pond
10.0 out of 10, Exceptional, (17)
"Very clean, cute lake house. Owner responsive, everything you need for a rental home. Lake and lake toys were so great! We really enjoyed our stay. Thank you!!! "
Lake Front with Amazing Sunsets on McGrath Pond
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
View of the lake from our dock.
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
2.0 star property
9.0 out of 10, Wonderful, (4)
"We enjoyed this house with plenty of comfortable spaces for our family! It had all the essentials and a nice Hot Tub to enjoy the cooler weather in. The beds were comfortable, plenty of pillows and extra blankets. The space in the basement was lovely. We did have to be mindful of the water pressure so someone could shower 1 at a time. But overall, this was a beautiful home away from home"
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
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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Other property types in Oakland

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
8.6 out of 10, Excellent, (14)
"We were traveling through New England and were looking forward to spending some time exploring the pond. We’d already been at the coast and were headed to more mountains and hiking inland over the rest of the week. We arrived and found they had put the paddleboards and kayaks away for the season. The neighbors on the cove still had lots of water toys set up. When we called, we were told that they put the Paddleboards and kayaks away October 1st. There was no mention of that in the listing and...
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Central Maine Apartment offering 4 Seasons of Fun.
Miscellaneous
Central Maine Apartment offering 4 Seasons of Fun.
10.0 out of 10, Exceptional, (32)
"This clean, spacious, comfortable place was just what we needed for our time spent in Maine. Gary and Irma thought of everything! "
The price is SAR 394
SAR 941 total
includes taxes & fees
25 Nov - 26 Nov
Central Maine Apartment offering 4 Seasons of Fun.
Cozy Long Pond Cottage: private mooring & shared dock
Come enjoy this warm cottage!
Cozy Long Pond Cottage: private mooring & shared dock
9.8 out of 10, Exceptional, (8)
"The stay was a very nice place and we will be coming back with the whole family next time. "
Cozy Long Pond Cottage: private mooring & shared dock
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.