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

Charming Wilton Vacation Rental w/ Fire Pit
Microwave, dishwasher, toaster, highchair
Charming Wilton Vacation Rental w/ Fire Pit
10.0 out of 10, Exceptional, (2)
"The property was exactly as advertised, well equipped and accommodating. Our family enjoyed the scenery, and splendor the area offered!!"
Charming Wilton Vacation Rental w/ Fire Pit
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
Property grounds
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
10.0 out of 10, Exceptional, (10)
"We were introduced to the Belgrade Lakes 15 years ago when our daughter went to summer camp in the area. We've been going back ever since because of all the incredible Mainers we met over the years and because Maine really is its own kind of vacationland. The Guest House where we had stayed closed and we always wanted to rent our own place to continue visiting and to share with family and friends. This lake house was absolutely perfect for us. It was exceptionally clean upon arrival, all...
Modern 4 BR Waterfront Lake House, beautiful Belgrade Lakes Area, Mt. Vernon, ME
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
Property grounds
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
2.0 star property
8.8 out of 10, Excellent, (3)
"Our son is an only child, and his favorite things to do are anything water-related… swimming, snorkeling, hot tubbing, kayaking, water trampoline… luckily this sweet little hidden gem had it ALL!!! We surprised him with a very much needed spontaneous overnight getaway, and the whole thing couldn’t have gone better. The owners were so lovely and made certain we were able to find the place easily. I followed her directions exactly, and they were perfect, no problems finding it! This home is...
4-bedroom Waterfront LAKEHOUSE in Maine. Hot tub, firepit, deck & private dock.
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Exterior
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
10.0 out of 10, Exceptional, (25)
"Everything is amazing: the property is new, clean, has everything one needs, everything works perfectly; the setting is on the water, quiet but yet close to things; very easy check in and check out steps. We really enjoyed our stay. Thank you. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Pool
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
10.0 out of 10, Exceptional, (231)
"We had a great time at the house! The owner was very communicative and the check in process was a breeze. The house had everything you’d want for a stay (except for grill tools! We couldn’t find them). The house was immaculate when we arrived too. Lake was gorgeous so we spent most of our time outside or on the porch!"
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Fridge, microwave, oven, stovetop
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.0 out of 10, Very Good, (14)
"Beautiful place. Loons, eagles, Ospreys, and good fishing. No A/C made a couple of days miserable when heat and humidity was in the mid-nineties. Many fans available, though. Would be more ethical to let people know before booking that tap water is not drinkable. Saying a kayak is available is a bit of a stretch (small plastic boat)."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Lakefront, Stunning Home only 30 min to Sugarloaf!
View from property
Lakefront, Stunning Home only 30 min to Sugarloaf!
10.0 out of 10, Exceptional, (22)
"Loved the house / views / lake side hangout. Property was amazing and absolutely would consider going back. "
Lakefront, Stunning Home only 30 min to Sugarloaf!
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
Property grounds
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
10.0 out of 10, Exceptional, (3)
"Great time!"
5 BED HOUSE + HOT TUB, SAUNA AND 600’ OF PRIVATE SHORELINE.
Private and Calming Waterfront to the Rescue!
Property grounds
Private and Calming Waterfront to the Rescue!
9.8 out of 10, Exceptional, (71)
"My husband and I plus our adult son, our daughter, son-in-law and our two young grandsons stayed at the lake house the last two weeks of August. What a beautiful, peaceful place. We loved hearing the loons calling every evening. We enjoyed using the provided paddle boat and kayaks. The outside of the house could use a little updating, specifically the front door deck, but the inside was renovated recently and very clean. We had a small family reunion on the Sunday after we checked in. The...
Private and Calming Waterfront to the Rescue!
SkyView Treehouse- Luxury Waterfront Retreat
Interior
SkyView Treehouse- Luxury Waterfront Retreat
10.0 out of 10, Exceptional, (3)
"Absolutely stunning home and location. From all the little details in the house and the host always made sure we had everything we needed and that he was just a text away if we needed anything at all. We had use of the kayaks and I would definitely suggest that because the scenery is just beautiful. Feras and his family are great hosts and I highly recommend them. "
The price is ￥62,601
￥120,620 total
includes taxes & fees
Sep 29 - Sep 30
SkyView Treehouse- Luxury Waterfront Retreat
Find Your Bliss at this Private and Captivating Lakeside Retreat
Smart TV, video games, foosball, table tennis
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
Cozy Cottage on water's edge of Lake Cobbosseecontee
View from property
Cozy Cottage on water's edge of Lake Cobbosseecontee
8.6 out of 10, Excellent, (9)
"Very nice, quiet and peaceful. The view every morning was wonderful."
Cozy Cottage on water's edge of Lake Cobbosseecontee
A soul soothing escape. Artistically built and lovingly maintained.
Exterior
A soul soothing escape. Artistically built and lovingly maintained.
10.0 out of 10, Exceptional, (27)
"10/10. We had a wonderful stay last week. The house had everything we needed and more. It is located in beautiful location and has stunning views! We can’t wait to come back."
The price is ￥40,505
￥65,437 total
includes taxes & fees
Oct 14 - Oct 15
A soul soothing escape. Artistically built and lovingly maintained.
A Belgrade Lakes Destination, Very Private, Tranquil [Handicap Accessible]
View from property
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]
Lake House Wooded Vacation Retreat and Nature Escape
Lake House Wooded Vacation Retreat and Nature Escape
9.8 out of 10, Exceptional, (45)
"This is such a perfect place to enjoy the tranquility of Clearwater Pond, with a well-appointed house in a great location. Will definitely return."
Lake House Wooded Vacation Retreat and Nature Escape
Peaceful Pleasant Point - Waterfront Maine Getaway
Pool
Peaceful Pleasant Point - Waterfront Maine Getaway
10.0 out of 10, Exceptional, (36)
"Peaceful, relaxing, great fishing, kayaking and hiking near by."
Peaceful Pleasant Point - Waterfront Maine Getaway
Pet-friendly, peaceful lakeside retreat on Cobboseecontee Lake peninsula
Lake
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 with Amazing Sunsets on McGrath Pond
Lake
Lake Front with Amazing Sunsets on McGrath Pond
10.0 out of 10, Exceptional, (16)
"Everything about the property and house is nothing short of perfection. Amenities galore. Close to Waterville and the highway. We didn’t want to leave. Will be returning next year if it’s available!"
Lake Front with Amazing Sunsets on McGrath Pond
Waterfront Sidney Getaway w/ Private Dock!
Interior
Waterfront Sidney Getaway w/ Private Dock!
Waterfront Sidney Getaway w/ Private Dock!
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard
Fridge, microwave, oven, stovetop
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard
2.0 star property
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard
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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

Central Maine Apartment offering 4 Seasons of Fun.
Smart TV
Central Maine Apartment offering 4 Seasons of Fun.
9.8 out of 10, Exceptional, (30)
"This property is Fantastic! All the comforts of home, with amenities we did not expect. Some food items in cupboard(soup, oatmeal,pancake mix…) Eggs, butter, milk, water, apple sauce in fridge! A fully stocked kitchen with silverware, pots, pans, and all kinds kitchen appliances. Even a bottle of wine! Comfy bed and bathroom was stocked with all necessities, in case you forgot anything! Plush bath towels, body wash, shampoo, and conditioner. Hosts were very fast to respond to all questions. They...
The price is ￥15,216
￥36,329 total
includes taxes & fees
Sep 30 - Oct 1
Central Maine Apartment offering 4 Seasons of Fun.
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Exterior
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
9.6 out of 10, Exceptional, (47)
"Very pretty spot. Nice lake, good for kayaking.we enjoyed the fire pit. "
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Fridge, microwave, oven, stovetop
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
8.8 out of 10, Excellent, (12)
"Everything we had hoped for. :)"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
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.