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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 121 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, (237)
"Everything that was promised was fulfilled. Host & caretaker were available and great to deal with. House was welcoming and comfortable in this cold-weather visit. We’d love to return in summer, the lake access clearly is wonderful."
Spectacular Cobbossee Lakefront with Hot Tub&Dog Friendly
Cozy House in the heart of Waterville Maine.
Living area

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (37)
"A lovely cozy house, well situated close to downtown and easy access to stores. The house was very clean and tidy. Cozy and felt like home, and worked out well for our Thanksgiving break with our college students. Would use againnif dates worked out."
Cozy House in the heart of Waterville Maine.
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Spacious dining room for your meals, game night, or remote office. (1)

Spacious Country Home w/ Hot Tub, near Colby/Thomas

9.8 out of 10, Exceptional, (16)
"The house was great in every way. "
Spacious Country Home w/ Hot Tub, near Colby/Thomas
Luxurious lakefront home with 750' of spectacular frontage on Great Pond
Property grounds

Luxurious lakefront home with 750' of spectacular frontage on Great Pond

10.0 out of 10, Exceptional, (3)
"Property was exactly as listed - view of the lake from the deck and living rooms was beautiful. Host was very available and responsive. We had a wonderful time - there were 3 generations of our family with up to 14 members staying at the home. We also hosted a larger family get-together with an additional 10 people for an afternoon with permission from the host. Everyone was impressed with the house, property, lake views, deck and dock. Four of our young adult cousins stayed in the log cabin...
Luxurious lakefront home with 750' of spectacular frontage on Great Pond
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

9.8 out of 10, Exceptional, (81)
"Great property, third tine here, excellent stocked kitchen"
3 Bedroom year round lakefront home on Three Mile Pond in South China, ME
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, (26)
"Great property!!"
The price is AED 893
AED 1,799 total
includes taxes & fees
19 Feb - 20 Feb
Lakefront, Stunning Home only 30 min to Sugarloaf!
Private and Calming Waterfront to the Rescue!
40 foot dock for boating, fishing and swimming

Private and Calming Waterfront to the Rescue!

9.6 out of 10, Exceptional, (76)
"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "
Private and Calming Waterfront to the Rescue!
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, (11)
"We headed up north to ring in the new year with friends who live in the area. We had an excellent stay. Enough space for all of the kids to visit and play and the adults to catch up! Lots of games and toys kept everyone busy and happy. Only negative is we didn’t get any snow…I love snow !! . Would definitely stay again. Owner just a text away for any questions/concerns very responsive. "
Cozy Long Pond Cottage: private mooring & shared dock
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
Cozy Keyes Cottage- Rare Lakefront Getaway

Cozy Keyes Cottage- Rare Lakefront Getaway

10.0 out of 10, Exceptional, (9)
"A perfect 5 weeks! Owner was always available and very quick to respond to all requests.a perfect experience in all ways!"
Cozy Keyes Cottage- Rare Lakefront Getaway
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.
Spacious 5-bedroom waterfront house in lovely Sidney with WiFi, AC
Property grounds

Spacious 5-bedroom waterfront house in lovely Sidney with WiFi, AC

Spacious 5-bedroom waterfront house in lovely Sidney with WiFi, AC
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME
Exterior

Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME

2.0 star property
10.0 out of 10, Exceptional, (2)
"We were just there for the weekend but if I could have stayed longer I would have . The house was clean and had plenty of space for everyone it was just my husband and me and our two grandkids but we had so much room and we did not even use the one room or the loft . The kitchen had everything you needed and then some I enjoyed the mint tea the owner had left for everyone. . They have soaps, bags,, spices, it all the little touches that make this place special. Can’t wait to go back."
Wildewood Haven - Charming 3-bedroom home located on Long Pond, Rome, ME
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard

Dog-friendly house with water sports gear, firepit, grill, & enclosed yard

2.0 star property
2.0 out of 10, (1)
Dog-friendly house with water sports gear, firepit, grill, & enclosed yard
Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan
Living area

Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan

2.0 star property
10.0 out of 10, Exceptional, (2)
"This house was perfect for our stay. We could host our family for meals and meetings. We could enjoy quiet evenings by ourselves and Walmart and grocery were close enough to walk to. "
Charming 2-bedroom house with AC, WiFi in enchanting Skowhegan
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
Beautiful view of Belgrade Stream from the private dock.

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very nice property that is clean and well managed "
Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock
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
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.
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, (33)
"Had a great stay over Xmas holiday seeing the family. ) "
The price is AED 386
AED 857 total
includes taxes & fees
25 Jan - 26 Jan
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, (11)
"We headed up north to ring in the new year with friends who live in the area. We had an excellent stay. Enough space for all of the kids to visit and play and the adults to catch up! Lots of games and toys kept everyone busy and happy. Only negative is we didn’t get any snow…I love snow !! . Would definitely stay again. Owner just a text away for any questions/concerns very responsive. "
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.