Book Holiday Homes in Winslow

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Featured Holiday Homes in Winslow

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

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

Mount Vernon
With a stay at this vacation home in Mount Vernon, you'll be on the waterfront, and 5.1 mi (8.2 km) from Belgrade Lakes Chain and 6.5 mi (10.4 km) from Maranacook ...
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting
Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Augusta
Located in Augusta, this vacation home is on the waterfront, within a 15-minute drive of VA Maine Healthcare System - Togus and Old Fort Western.
Private and Calming Waterfront to the Rescue!
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

Beautiful lakeside 4 bedroom retreat with private dock and walkout basement

2 out of 5
Oakland
Located in Oakland, this vacation home is on the waterfront, a 1-minute drive from Belgrade Lakes Chain and 6 minutes from Tree Spirits.
Beautiful lakeside 4 bedroom retreat with private dock and walkout basement
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Idyllic Washington Retreat w/ Fire Pit & Yard

Idyllic Washington Retreat w/ Fire Pit & Yard

Washington
When you stay at this vacation home in Washington, you'll be 13 minutes by car from Morse's Sauerkraut.
Idyllic Washington Retreat w/ Fire Pit & Yard
The Modern Maine Retreat

The Modern Maine Retreat

Oakland
With a stay at this vacation home in Oakland, you'll be within a 5-minute drive of Belgrade Lakes Chain and Tree Spirits.
The Modern Maine Retreat
Brand New Waterfront Lake House (completed July 2021)

Brand New Waterfront Lake House (completed July 2021)

Belgrade
Located in Belgrade, this vacation home is on a lake, within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Brand New Waterfront Lake House (completed July 2021)
Charming 4-bedroom log home with WiFi and AC in pleasant Liberty

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

Liberty
Located in Liberty, this vacation home is a 4-minute drive from St George Lake and 8 minutes from Lake Saint George State Park.
Charming 4-bedroom log home with WiFi and AC in pleasant Liberty
Cozy House in the heart of Waterville Maine.

Cozy House in the heart of Waterville Maine.

Waterville
With a stay at this vacation home in Waterville, you'll be within a 5-minute drive of Redington Museum and Common Street Arts.
Cozy House in the heart of Waterville Maine.
Spectacular Location  Reasonably Priced

Spectacular Location Reasonably Priced

Belgrade
Located in Belgrade, this vacation home is on the waterfront, within a 15-minute drive of Belgrade Lakes Chain and Belgrade Lakes Golf.
Spectacular Location Reasonably Priced
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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.

Winslow Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winslow vacation homes are the perfect way for you to wing it.

Holiday houses in Winslow let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winslow in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winslow adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winslow with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winslow vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winslow Holiday Homes essential information

Accommodation
117 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$249
Popular accommodation
Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting, Private and Calming Waterfront to the Rescue!, Beautiful lakeside 4 bedroom retreat with private dock and walkout basement, Idyllic Washington Retreat w/ Fire Pit & Yard, The Modern Maine Retreat, Brand New Waterfront Lake House (completed July 2021), Charming 4-bedroom log home with WiFi and AC in pleasant Liberty, Cozy House in the heart of Waterville Maine., Spectacular Location Reasonably Priced

Top trending hotels in Winslow

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is AU$243 per night from 13 Apr to 14 Apr
AU$243
includes taxes & fees
13 Apr - 14 Apr
A stay at Maine Evergreen Hotel, Ascend Hotel Collection places you in the heart of Augusta, within a 10-minute drive of Augusta Civic Center and Capitol ...
Maine Evergreen Hotel, Ascend Hotel Collection
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 out of 5
332 Main St, Waterville, ME
Fully refundable
The price is AU$201 per night from 13 Apr to 14 Apr
AU$201
includes taxes & fees
13 Apr - 14 Apr
With a stay at Holiday Inn Express & Suites Waterville - North by IHG in Waterville, you'll be within a 5-minute drive of First Congregational Church and Kennebec ...
Holiday Inn Express & Suites Waterville - North by IHG
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 13 Apr to 14 Apr
AU$249
includes taxes & fees
13 Apr - 14 Apr
Located in Augusta, Senator Inn & Spa is in a shopping district, within a 5-minute drive of Turnpike Mall and Blaine House.
Senator Inn & Spa
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Best Western Plus Waterville Grand Hotel

Best Western Plus Waterville Grand Hotel

3 out of 5
375 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 6 Apr to 7 Apr
AU$237
includes taxes & fees
6 Apr - 7 Apr
Located in Waterville, Best Western Plus Waterville Grand Hotel is within a 5-minute drive of First Congregational Church and Kennebec River.
Best Western Plus Waterville Grand Hotel
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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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^Subject to availability and chosen travel dates.