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Vacation Homes in Winslow

Our top choices for Winslow vacation homes

Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

9.2 out of 10, Wonderful, (21)
"The house & deck were very nice with beautiful view of the lake. It could use some typical amenities like tissues, hair dryer, etc. The main problem is getting to the house. It’s a 3/4 mile drive down a narrow stone road riddled with potholes and bumps. I was afraid I was going to do damage to the rental car and that’s driving at or lower than the 15mph speed limit! "
Lakefront home on Long Pond with private dock, firepit & woodstove- dog-friendly

New Waterfront Lake House - completed 2021

10.0 out of 10, Exceptional, (27)
"We enjoyed our stay at this charming Belgrade lake house. The house was beautifully decorated, immaculate, and cozy for our week long stay while attending Colby graduation. Host was super organized, communicative, and provided everything we needed. Would definitely recommend staying here."
New Waterfront Lake House - completed 2021

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

9.8 out of 10, Exceptional, (27)
"This house has everything for a weekend family vacay; you can spend the whole weekend enjoying the house & amenities such as the hot tub!"
Spacious Country Home w/ Hot Tub, near Colby/Thomas

3 Bedroom year round lakefront home on Three Mile Pond with private dock

9.8 out of 10, Exceptional, (90)
"We were very comfortable and enjoyed the lake house. Thank you!"
3 Bedroom year round lakefront home on Three Mile Pond with private dock

Spectacular Location Reasonably Priced

9.6 out of 10, Exceptional, (30)
"Peaceful and scenic location"
Spectacular Location Reasonably Priced

Discover Oakland charm near Colby College 10 min

2.0 star property
10.0 out of 10, Exceptional, (3)
"New, clean and had everything we needed. "
Discover Oakland charm near Colby College 10 min

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

10.0 out of 10, Exceptional, (12)
"Nice time"
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Belgrade Lake house with Dock!

10.0 out of 10, Exceptional, (1)
"This property was so peaceful and quiet. It sits on a large lot with lots of privacy. The walk down to the dock is fun for kids, lots of rocks and it’s a little trail. We spent most of our time down at the dock. The views were spectacular, beautiful reflections in the water each morning, calm quiet lake and the sunset right in front of us each night. It wasn’t buggy and we used the kayak, but wear water shorts bc it does take in some water. We also brought our own paddle board and would highly...
Belgrade Lake house with Dock!

The Modern Maine Retreat

8.8 out of 10, Excellent, (11)
"Multi generation family in town to visit other family. Kitchen adequate for meal prep, "
The Modern Maine Retreat

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

NEW! Long Pond Lake View Getaway w/HOT TUB, ME

The Maine Experience: Where expansive nature meets modern comfort...

The price is AED 890
AED 1,071 total
includes taxes & fees
29 Sep - 30 Sep
The Maine Experience: Where expansive nature meets modern comfort...

Cozy House in the heart of Waterville Maine.

9.6 out of 10, Exceptional, (43)
"Loved the cozy home! We would stay there again in a heartbeat. The only thing that we would have been nice is if there was a tv in the main bedroom, but that’s just a personal preference. "
Cozy House in the heart of Waterville Maine.

Small cottage house, centered on 100 acres surround by hills, lake, and cattle.

2.0 star property
10.0 out of 10, Exceptional, (3)
"The pictures don’t do justice to the great views of trees, hills and a lake in the distance. Really enjoyed our short stay. The two single air mattresses were much appreciated. It was clean and new. We got to see a porcupine, deer, cows and a donkey. "
Small cottage house, centered on 100 acres surround by hills, lake, and cattle.

Charming 4-bedroom log home with WiFi and AC in pleasant Liberty

6.0 out of 10, (1)
"The cabin is located on a hillside with a lovely view of the valley. We were were unable to enjoy the breeze as the door handle to one of the two sets of French doors was broken off. The living room furniture was up close to both sets so the only way to open the other set completely was by moving the living room furniture. We opened the kitchen window (which had a storm window/screen). Unfortunately there were dead flies piled in between the window and the storm screen so we closed it so...
Charming 4-bedroom log home with WiFi and AC in pleasant Liberty

Idyllic Washington Retreat w/ Fire Pit & Yard

9.0 out of 10, Wonderful, (15)
"This place was perfect for our needs. The beds were really comfortable and the 6 of us slept great. Thank you for having us."
Idyllic Washington Retreat w/ Fire Pit & Yard

Charming Lakeview House with Deck, Cozy Fireplace and firepit

10.0 out of 10, Exceptional, (1)
"Nice location, beautiful home. Nicely set up and great detail to comfort, supplies/needs. Didn't need a thing and felt at home in a peaceful place. Highly recommend!!"
Charming Lakeview House with Deck, Cozy Fireplace and firepit

Lovely 1- bedroom rental unit with free parking

Lovely 1- bedroom rental unit with free parking

Cozy Long Pond Cottage: private mooring & shared dock

9.8 out of 10, Exceptional, (17)
"Very nice weekend and great host- very responsive!"
Cozy Long Pond Cottage: private mooring & shared dock

Find Your Bliss at this Private and Captivating Lakeside Retreat

10.0 out of 10, Exceptional, (25)
"Great stay, amazing house and property!"
Find Your Bliss at this Private and Captivating Lakeside Retreat

SkyView Treehouse Lakefront Private Hot Tub

10.0 out of 10, Exceptional, (5)
"We had a fantastic stay at the sky view treehouse. It was beautiful and very clean. Feras’ attention to detail was amazing and it made our stay better than any hotel."
The price is AED 2,332
AED 4,048 total
includes taxes & fees
13 Sep - 14 Sep
SkyView Treehouse Lakefront Private Hot Tub
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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Top Winslow Hotel Reviews