Winn Holiday Rentals

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Holiday Rentals in Winn

Lakefront home with something to enjoy for every season!
TV, video games, DVD player, table football

Lakefront home with something to enjoy for every season!

9.8 out of 10, Exceptional, (162)
"James provided my friend and I with the perfect accommodations for a long weekend getaway! Checkin was very easy, the house was clean, and everything was very thoughtful. The kitchen was so well stocked with cookware and all of the small appliances (coffeemaker, toaster oven, air fryer, slow cooker, you name it). The beds were comfortable and there were plenty of towels. We LOVED the quadruple sliding glass doors that let us lounge in the living room but still feel connected to the outdoors!...
Lakefront home with something to enjoy for every season!
Schlafmans Hollow Solar Cabins
Cookware/dishes/utensils, dining tables

Schlafmans Hollow Solar Cabins

3.0 star property
9.8 out of 10, Exceptional, (10)
"Scott was a fantastic host! Everything was clean and comfortable, he was very accommodating and super friendly! Would definitely stay here again!!"
Schlafmans Hollow Solar Cabins
Rustic Cabin on Penobscot River (Pet-Friendly!)
Miscellaneous

Rustic Cabin on Penobscot River (Pet-Friendly!)

9.8 out of 10, Exceptional, (35)
"Awesome water views, quiet and peaceful. I would just mention the steep stairs to loft. Otherwise, very satisfied. Would definitely book again!"
The price is AU$283
includes taxes & fees
2 Dec - 3 Dec
Rustic Cabin on Penobscot River (Pet-Friendly!)
Maine Lakeside Retreat
Snow and ski sports

Maine Lakeside Retreat

10.0 out of 10, Exceptional, (31)
"We loved our little hideaway!!! It was perfect for our needs & we are definitely talking about next time! "
Maine Lakeside Retreat
Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!
Miscellaneous

Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!

9.8 out of 10, Exceptional, (26)
"It was good. Peaceful"
Welcome to our Waterfront Cabin in Northern, Maine. A great place to relax!!
House close to Mt. Kathadin, Baxter State Park
Property grounds

House close to Mt. Kathadin, Baxter State Park

8.4 out of 10, Very good, (30)
"Home was just as listed. Perfect size for 3-4 people. Quiet neighborhood, comfortable accomodations close to Baxter State Park. Property manager very gracious and accomodating when I made an error in our departure date. I would definitely stay again."
House close to Mt. Kathadin, Baxter State Park
Lakeside Getaway on Upper Coldstream Pond
Miscellaneous

Lakeside Getaway on Upper Coldstream Pond

9.6 out of 10, Exceptional, (12)
"We loved the location of this property. We have our own kayaks and we loved how easy it was to get them in and out of the water. We also enjoyed sitting on the wraparound porch where there is a nice breeze coming off of the other lake across the street. The kitchen is recently renovated and the bedrooms are nice and cozy. I have also never seen a place so well stocked with firewood. Property managers are ver friendly and helpful. 10/10."
Lakeside Getaway on Upper Coldstream Pond
Lake House
Fridge, microwave, oven, stovetop

Lake House

10.0 out of 10, Exceptional, (35)
"Another awesome company retreat in the mountains of Maine. As always, the house was absolutely fantastic. Everything was clean and in working order. Communication with host was quick and efficient. Thank you so much for letting us use your home we absolutely love it. Hope to be back again next year."
Lake House
Log Cabin On Quiet Wilderness Lake In Downeast Lakes Region Of Maine
Interior

Log Cabin On Quiet Wilderness Lake In Downeast Lakes Region Of Maine

10.0 out of 10, Exceptional, (20)
"Wonderful property, beautiful lake, nice house but it needs some improvements. It need to be cleaner. I know it is a wilderness camp but it needs a through cleaning. All food items should be removed after each guest departs. Food items attract mice and the house is infested with mice. We caught over a dozen while we were there. No one has cleaned behind the washer dryer in the last year. The throw on the couch was filthy. It needs a thorough cleaning. The stairs to the 2nd floor need to be...
Log Cabin On Quiet Wilderness Lake In Downeast Lakes Region Of Maine
Lake Side Cottage, Central Maine, Private dock, Great Sunsets. Very Calming.
Pool

Lake Side Cottage, Central Maine, Private dock, Great Sunsets. Very Calming.

9.4 out of 10, Exceptional, (20)
"It was an older cabin but very comfortable and everything we needed. Was very quiet but close to town so we could run and get pizza and things we need only 15 minutes to Pat's enjoyed the kayaksPizza in Lincoln."
Lake Side Cottage, Central Maine, Private dock, Great Sunsets. Very Calming.
New Peaceful Home located on Mattanawcook Pond, Lincoln
Exterior

New Peaceful Home located on Mattanawcook Pond, Lincoln

10.0 out of 10, Exceptional, (13)
"Well appointed, clean, private, excellent value….loons peacefully calling across the beautiful waters will long remain in our memories. We will return next year. "
New Peaceful Home located on Mattanawcook Pond, Lincoln
Lake House Oasis on Cold Stream
Terrace/patio

Lake House Oasis on Cold Stream

9.8 out of 10, Exceptional, (8)
"Great lake setting. Nicely appointed. Rooms and beds were great. You have to be ok for multi bedrooms accessing the one bathroom located in the master. The lofted singles being accessed via a pull down attic ladder was an issue. Overall it is a great property, but has a couple of quirks. If you are a smaller group, it likely won't have any impact. We appreciate all of the excellent responses and service from Jason in preparation for our stay. "
Lake House Oasis on Cold Stream
Beautiful Family Getaway on Private Lakefront
3 bedrooms, iron/ironing board, travel cot, free WiFi

Beautiful Family Getaway on Private Lakefront

10.0 out of 10, Exceptional, (6)
"We stay in a lot of VRBO homes and this was a great experience. Many little and appreciated touches that a lot of owners do not think of. Plenty of room for the whole fam. My college aged kids loved the space to spread out and really enjoyed getting out on the lake. The kitchen had everything we needed to make meals. Both my husband and I had to work a bit and the internet did not fail us. My husband is from Lincoln and thought the location was great, especially since we were running into...
Beautiful Family Getaway on Private Lakefront
Schlafman's Hollow Solar Cabin 1
Property grounds

Schlafman's Hollow Solar Cabin 1

10.0 out of 10, Exceptional, (1)
"Nice and clean. All renewable energy sources. Beautiful area. Peaceful, could do my work and focus."
Schlafman's Hollow Solar Cabin 1
Cabin on the water!
Property grounds

Cabin on the water!

9.4 out of 10, Exceptional, (17)
"Great location to the local trails for ATV riding."
Cabin on the water!
Waterfront Lincoln Home w/ 2 Decks & Fire Pit
Terrace/patio

Waterfront Lincoln Home w/ 2 Decks & Fire Pit

6.0 out of 10, (1)
Waterfront Lincoln Home w/ 2 Decks & Fire Pit
Bear's Den 1 Bed/1 Bath Charming Rustic Log Cabin
Property grounds

Bear's Den 1 Bed/1 Bath Charming Rustic Log Cabin

10.0 out of 10, Exceptional, (6)
"The cabin was cozy and well equipped and the River view was beautiful. I recommend this place to anyone looking to get away and explore Baxter State Park. "
Bear's Den 1 Bed/1 Bath Charming Rustic Log Cabin
Quiet cabin on Center Pond.
Property grounds

Quiet cabin on Center Pond.

10.0 out of 10, Exceptional, (1)
"Open on pond. Everyday a different view. This is a traditional fish camp cabin."
Quiet cabin on Center Pond.
Moose's Lair 1 Bed/1 Bath Charming Rustic Log Cabin
Property grounds

Moose's Lair 1 Bed/1 Bath Charming Rustic Log Cabin

9.4 out of 10, Exceptional, (8)
"Property was great. FYI the one of the pictures makes it look like the river runs right to lawn but there is a steep incline to access river which if I had known I wouldn’t have brought my kayak. Otherwise the pictures are good representation of the property."
Moose's Lair 1 Bed/1 Bath Charming Rustic Log Cabin
The Loon House is on beautiful, clean spring fed Silver lake.
Smart TV, DVD player, books

The Loon House is on beautiful, clean spring fed Silver lake.

10.0 out of 10, Exceptional, (22)
"The house was beautiful and very comfortable. It was very well stocked. The lake and dock had nice easy access with sandy beach. The view was incredible and the Loons and we even had a Bald Eagle fly over. Great memories made with our Daughters and grandkids"
The Loon House is on beautiful, clean spring fed Silver lake.
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 types of properties in Winn you may be interested in

Gateway Inn
Lobby sitting area

Gateway Inn

2.5 star property
8.4 out of 10, Very good, (353)
"Right in a location where I needed a motel."
The price is AU$168
includes taxes & fees
28 Nov - 29 Nov
Gateway Inn
Briarwood Motor Inn
Classic Room, 2 Queen Beds

Briarwood Motor Inn

2.5 star property
9.0 out of 10, Wonderful, (152)
"They accommodated my late arrival. Flight was delayed and wouldn’t have made it in time for check in. Room was spacious and clean. Really quiet as well. When we come back we will stay here again. "
The price is AU$195
includes taxes & fees
16 Dec - 17 Dec
Briarwood Motor Inn
Rustic Cabin on Penobscot River (Pet-Friendly!)
Miscellaneous

Rustic Cabin on Penobscot River (Pet-Friendly!)

9.8 out of 10, Exceptional, (35)
"Awesome water views, quiet and peaceful. I would just mention the steep stairs to loft. Otherwise, very satisfied. Would definitely book again!"
The price is AU$283
includes taxes & fees
2 Dec - 3 Dec
Rustic Cabin on Penobscot River (Pet-Friendly!)
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Frequently asked questions

Can I find a holiday rental in Winn?

Yes, there are holiday rentals close to the most popular sights in Winn, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winn has to offer?

House close to Mt. Kathadin, Baxter State Park: This holiday home rental outside of Winn is located on a river, and has a garden, a selection of games and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Winn?

While exploring the area, visit the sights like Lincoln Memorial Library, Mt. Jefferson and Jato Highlands Golf Course.

What’s a holiday rental in Winn like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winn. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip.