Winslow Holiday Rentals

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Holiday Rentals in Winslow

Lighthouse Lane

10.0 out of 10, Exceptional, (59)
"Check in and check out was super easy. Photos are super accurate and the property is beautiful. Thank you for sharing your beautiful with us!"
The price is NZ$978
includes taxes & fees
7 Sept - 8 Sept
Lighthouse Lane

Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

2.0 star property
10.0 out of 10, Exceptional, (5)
"Wonderful hosts, they thought of everything we might need including many nice extra touches! Beautiful quiet spot with the opportunity to paddle boat, kayak, canoe, swim, fish, enjoy campfires, outdoor grilling, observe wildlife (Osprey, Bald Eagle, Deer)"
Maine Cabin Masters Camp completely redone waiting for a Lake loving family !

Large Secluded Cabin on the Lake - NOW SLEEPS 10

10.0 out of 10, Exceptional, (57)
"Would stay there again in a heartbeat, above our expectations "
Large Secluded Cabin on the Lake - NOW SLEEPS 10

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes

9.4 out of 10, Exceptional, (58)
"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

Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

9.0 out of 10, Wonderful, (2)
"Cozy cottage by the lake. Great scenery and wildlife. Great communication with host. "
Charming 3-bedroom waterfront cottage with AC, WiFi and spectacular sunset views

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!

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

9.2 out of 10, Wonderful, (23)
"Great view, clean, central a/c, even the ppl using powerboats (4th of July!) were respectful. Exactly the getaway I needed!"
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (3)
"Great stay. Would stay here again if in the area."
The price is NZ$384
includes taxes & fees
26 Aug - 27 Aug
Sister A-Frame in Woods B

Mountainside cabin "Sasquatch Haven"

9.4 out of 10, Exceptional, (20)
"Wonderful stay!"
Mountainside cabin "Sasquatch Haven"

Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

9.8 out of 10, Exceptional, (32)
"This place was perfect for our 3-night stay. Inside, it hits the sweet spot between well-equipped but uncluttered. The bird-watching overlooking the water was fantastic - from huge bald eagles to petite hummingbirds. "
Weekly discounts avail. Get away at this New house on Lovejoy Pond in Albion

Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House

8.0 out of 10, Very good, (2)
"My husband and his good friend stayed there and absolutely loved everything about the house, location and the host. "
Serene Cabin with Lakefront Access, Cozy Fire Pit, and Bunk House

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

10.0 out of 10, Exceptional, (11)
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

7.6 out of 10, Good, (22)
"We enjoyed this place and will definitely come back again."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Sunset Chalet Lakefront Hot Tub Game Room

10.0 out of 10, Exceptional, (25)
"Very nice quiet location. Loved the game room. Relaxing stay."
The price is NZ$1,274
includes taxes & fees
31 Aug - 1 Sept
Sunset Chalet Lakefront Hot Tub Game Room

Private Dock on Messalonskee Lake: Cozy Cottage!

2.0 star property
9.6 out of 10, Exceptional, (5)
"Great spot right on the lake, True to what was listed. The beds weren’t very comfortable but otherwise everything was great."
Private Dock on Messalonskee Lake: Cozy Cottage!

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

Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit

6.4 out of 10, (7)
"The listing stated there were upstairs tenants. Long story short, on Thanksgiving when they arrived home to me enjoying an outdoor fire, the accused me of using their firewood, I had brought my own. Then another night I left to do an activity with my kids and returned to not being able to park, due to them taking up three spaces with their truck. They were noisy every night until midnight and up every morning by 7a. In have no living family besides my kids and I was looking for a relaxing...
Lakefront Home on Togus Pond with 2 Decks, Great View & Shared Canoe/Firepit

Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

9.0 out of 10, Wonderful, (23)
"We had an amazing week. This is the perfect lake cabin… swimming, boating, tubing, campfires at night… we even used a projector to do an outdoor movie night. The owners are very responsive and helpful. We would definitely stay here again."
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

9.8 out of 10, Exceptional, (27)
"This was an amazing experience and the vision that the owners have is amazing I highly recommend this place"
The price is NZ$264
includes taxes & fees
14 Sept - 15 Sept
Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

Classic and adorable Maine camp on North Pond in the Belgrade Lakes

10.0 out of 10, Exceptional, (31)
"Beautiful cabin in an idyllic location! We always enjoy our week at Blessings and hope to return!"
Classic and adorable Maine camp on North Pond in the Belgrade Lakes
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

Frequently asked questions

Can I find a holiday rental in Winslow?

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

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

Belgrade Lake house with Dock!: This holiday home rental outside of Winslow is located on a lake, and has a garden, a BBQ and laundry facilities to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Winslow?

Explore the area and family-friendly sights such as Maine State Museum, or get out into nature at a spot like Kennebec River. Fort Halifax and Waterville Opera House are a couple of places you'll find in the wider area.

What’s a holiday rental in Winslow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winslow. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for families.