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Winslow Holiday Rentals

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Bedrooms

Bathrooms

Amenities

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Property type

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Distance from

5 mi
50 rentals in Winslow.
All The Comforts of Home, holiday rental in Winslow
All The Comforts of Home, holiday rental in Winslow
All The Comforts of Home, holiday rental in Winslow

All The Comforts of Home

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The following properties within 20 miles of Winslow match all your filters:
Get away from it all at this cottage on East pond in Oakland Maine, holiday rental in Winslow
Get away from it all at this cottage on East pond in Oakland Maine, holiday rental in Winslow
Get away from it all at this cottage on East pond in Oakland Maine, holiday rental in Winslow

Get away from it all at this cottage on East pond in Oakland Maine

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront home on McGrath Pond - once featured on Maine Cabin Masters, holiday rental in Winslow
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters, holiday rental in Winslow
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters, holiday rental in Winslow

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Quiet, Lakefront home with private sandy beach, holiday rental in Winslow
Quiet, Lakefront home with private sandy beach, holiday rental in Winslow
Quiet, Lakefront home with private sandy beach, holiday rental in Winslow

Quiet, Lakefront home with private sandy beach

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps
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Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok, holiday rental in Winslow
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok, holiday rental in Winslow
Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok, holiday rental in Winslow

Lakefront home with water-view deck, kayaks, gas grill, & washer/dryer - dogs ok

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet setting 1 minute drive to China lake boat launch and ATV trail, holiday rental in Winslow
Quiet setting 1 minute drive to China lake boat launch and ATV trail, holiday rental in Winslow
Quiet setting 1 minute drive to China lake boat launch and ATV trail, holiday rental in Winslow

Quiet setting 1 minute drive to China lake boat launch and ATV trail

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes, holiday rental in Winslow
Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes, holiday rental in Winslow
Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes, holiday rental in Winslow

Modern lakeside log cabin on pristine East Pond Oakland Maine's Belgrade Lakes

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Full home, 7mins to lakes, 10mins to WTVL/Augusta w/ Hottub, holiday rental in Winslow
Full home, 7mins to lakes, 10mins to WTVL/Augusta w/ Hottub, holiday rental in Winslow
Full home, 7mins to lakes, 10mins to WTVL/Augusta w/ Hottub, holiday rental in Winslow

Full home, 7mins to lakes, 10mins to WTVL/Augusta w/ Hottub

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Classy AF Home Steps from Colby and Trails, holiday rental in Winslow
Classy AF Home Steps from Colby and Trails, holiday rental in Winslow
Classy AF Home Steps from Colby and Trails, holiday rental in Winslow

Classy AF Home Steps from Colby and Trails

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Get away at this new house on Lovejoy Pond in Albion Maine, holiday rental in Winslow
Get away at this new house on Lovejoy Pond in Albion Maine, holiday rental in Winslow
Get away at this new house on Lovejoy Pond in Albion Maine, holiday rental in Winslow

Get away at this new house on Lovejoy Pond in Albion Maine

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gramp's Camp, holiday rental in Winslow
Gramp's Camp, holiday rental in Winslow
Gramp's Camp, holiday rental in Winslow

Gramp's Camp

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 2
Match: Sleeps
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Wendell Cottage, holiday rental in Winslow
Wendell Cottage, holiday rental in Winslow
Wendell Cottage, holiday rental in Winslow

Wendell Cottage

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
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Mystic Bungalow, holiday rental in Winslow
Mystic Bungalow, holiday rental in Winslow
Mystic Bungalow, holiday rental in Winslow

Mystic Bungalow

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 3
Match: Sleeps
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Hidden Cove Camp, holiday rental in Winslow
Hidden Cove Camp, holiday rental in Winslow
Hidden Cove Camp, holiday rental in Winslow

Hidden Cove Camp

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront ground floor apartment on Snow Pond, close to Colby and Thomas College, holiday rental in Winslow
Lakefront ground floor apartment on Snow Pond, close to Colby and Thomas College, holiday rental in Winslow
Lakefront ground floor apartment on Snow Pond, close to Colby and Thomas College, holiday rental in Winslow

Lakefront ground floor apartment on Snow Pond, close to Colby and Thomas College

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy lakeshore cottage, sunset, sunrise views mid Maine near coast, wifi, holiday rental in Winslow
Cozy lakeshore cottage, sunset, sunrise views mid Maine near coast, wifi, holiday rental in Winslow
Cozy lakeshore cottage, sunset, sunrise views mid Maine near coast, wifi, holiday rental in Winslow

Cozy lakeshore cottage, sunset, sunrise views mid Maine near coast, wifi

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Lavender Haze Cottage in the Woods, holiday rental in Winslow
Lavender Haze Cottage in the Woods, holiday rental in Winslow
Lavender Haze Cottage in the Woods, holiday rental in Winslow

Lavender Haze Cottage in the Woods

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access, holiday rental in Winslow
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access, holiday rental in Winslow
Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access, holiday rental in Winslow

Lakefront, dog-friendly cottage with screened porch, firepit, WiFi & lake access

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Farmhouse Oasis: Renovated Apt Near Downtown, holiday rental in Winslow
Farmhouse Oasis: Renovated Apt Near Downtown, holiday rental in Winslow
Farmhouse Oasis: Renovated Apt Near Downtown, holiday rental in Winslow

Farmhouse Oasis: Renovated Apt Near Downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Cottage on Ellis Pond-Cabin #2 at Kozy Cove, holiday rental in Winslow
Cozy Cottage on Ellis Pond-Cabin #2 at Kozy Cove, holiday rental in Winslow
Cozy Cottage on Ellis Pond-Cabin #2 at Kozy Cove, holiday rental in Winslow

Cozy Cottage on Ellis Pond-Cabin #2 at Kozy Cove

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Quaint Oakland Getaway on East Pond Lake!, holiday rental in Winslow
Quaint Oakland Getaway on East Pond Lake!, holiday rental in Winslow
Quaint Oakland Getaway on East Pond Lake!, holiday rental in Winslow

Quaint Oakland Getaway on East Pond Lake!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Central Maine Apartment offering 4 Seasons of Fun., holiday rental in Winslow
Central Maine Apartment offering 4 Seasons of Fun., holiday rental in Winslow
Central Maine Apartment offering 4 Seasons of Fun., holiday rental in Winslow

Central Maine Apartment offering 4 Seasons of Fun.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Belgrade Lakes Salmon Waterfront cottage, holiday rental in Winslow
Belgrade Lakes Salmon Waterfront cottage, holiday rental in Winslow
Belgrade Lakes Salmon Waterfront cottage, holiday rental in Winslow

Belgrade Lakes Salmon Waterfront cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Large open concept Apartment in downtown Waterville.  Completely renovated, holiday rental in Winslow
Large open concept Apartment in downtown Waterville.  Completely renovated, holiday rental in Winslow
Large open concept Apartment in downtown Waterville.  Completely renovated, holiday rental in Winslow

Large open concept Apartment in downtown Waterville. Completely renovated

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Little Cottage, holiday rental in Winslow
Quaint Little Cottage, holiday rental in Winslow
Quaint Little Cottage, holiday rental in Winslow

Quaint Little Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New- Golf, Fishing, Kayaks & Waterfront - Private Cottage, holiday rental in Winslow
New- Golf, Fishing, Kayaks & Waterfront - Private Cottage, holiday rental in Winslow
New- Golf, Fishing, Kayaks & Waterfront - Private Cottage, holiday rental in Winslow

New- Golf, Fishing, Kayaks & Waterfront - Private Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy House in the heart of Waterville Maine., holiday rental in Winslow
Cozy House in the heart of Waterville Maine., holiday rental in Winslow
Cozy House in the heart of Waterville Maine., holiday rental in Winslow

Cozy House in the heart of Waterville Maine.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Maine Lakefront Cabin near Colby College, holiday rental in Winslow
Cozy Maine Lakefront Cabin near Colby College, holiday rental in Winslow
Cozy Maine Lakefront Cabin near Colby College, holiday rental in Winslow

Cozy Maine Lakefront Cabin near Colby College

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Get away from it all at this cottage on Lovejoy pond in Albion Maine, holiday rental in Winslow
Get away from it all at this cottage on Lovejoy pond in Albion Maine, holiday rental in Winslow
Get away from it all at this cottage on Lovejoy pond in Albion Maine, holiday rental in Winslow

Get away from it all at this cottage on Lovejoy pond in Albion Maine

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cottage on Ellis Pond-Cabin #1 at Kozy Cove, holiday rental in Winslow
Cozy Cottage on Ellis Pond-Cabin #1 at Kozy Cove, holiday rental in Winslow
Cozy Cottage on Ellis Pond-Cabin #1 at Kozy Cove, holiday rental in Winslow

Cozy Cottage on Ellis Pond-Cabin #1 at Kozy Cove

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rustic & Cozy Cabin – Steps away from beautiful Salmon Lake, holiday rental in Winslow
Rustic & Cozy Cabin – Steps away from beautiful Salmon Lake, holiday rental in Winslow
Rustic & Cozy Cabin – Steps away from beautiful Salmon Lake, holiday rental in Winslow

Rustic & Cozy Cabin – Steps away from beautiful Salmon Lake

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Half-House Monthly Rental: Lovely Historic Waterfront Home on Kennebec River, holiday rental in Winslow
Half-House Monthly Rental: Lovely Historic Waterfront Home on Kennebec River, holiday rental in Winslow
Half-House Monthly Rental: Lovely Historic Waterfront Home on Kennebec River, holiday rental in Winslow

Half-House Monthly Rental: Lovely Historic Waterfront Home on Kennebec River

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Belgrade Lakes McGrath Pond, holiday rental in Winslow
Belgrade Lakes McGrath Pond, holiday rental in Winslow
Belgrade Lakes McGrath Pond, holiday rental in Winslow

Belgrade Lakes McGrath Pond

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe, holiday rental in Winslow
Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe, holiday rental in Winslow
Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe, holiday rental in Winslow

Modern Lakefront Camp on East Pond - cozy fire pit, 3 kayaks, canoe

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Cottage 3BR Mid Maine, China Lake, Belgrade close to coast, wifi, holiday rental in Winslow
Lakefront Cottage 3BR Mid Maine, China Lake, Belgrade close to coast, wifi, holiday rental in Winslow
Lakefront Cottage 3BR Mid Maine, China Lake, Belgrade close to coast, wifi, holiday rental in Winslow

Lakefront Cottage 3BR Mid Maine, China Lake, Belgrade close to coast, wifi

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Belgrade lakes waterfront on Messalonskee 4 bedroom cabin, holiday rental in Winslow
Belgrade lakes waterfront on Messalonskee 4 bedroom cabin, holiday rental in Winslow
Belgrade lakes waterfront on Messalonskee 4 bedroom cabin, holiday rental in Winslow

Belgrade lakes waterfront on Messalonskee 4 bedroom cabin

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!, holiday rental in Winslow
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!, holiday rental in Winslow
Cozy Open Concept Lake House with Large Deck & Waterfront, perfect for families!, holiday rental in Winslow

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Midcoast Vacation Rental Near Waterville!, holiday rental in Winslow
Cozy Midcoast Vacation Rental Near Waterville!, holiday rental in Winslow
Cozy Midcoast Vacation Rental Near Waterville!, holiday rental in Winslow

Cozy Midcoast Vacation Rental Near Waterville!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Screen Porch with see thru roof, BQ, 30' from sandy beach,  canoe and 3 kayaks, holiday rental in Winslow
Screen Porch with see thru roof, BQ, 30' from sandy beach,  canoe and 3 kayaks, holiday rental in Winslow
Screen Porch with see thru roof, BQ, 30' from sandy beach,  canoe and 3 kayaks, holiday rental in Winslow

Screen Porch with see thru roof, BQ, 30' from sandy beach, canoe and 3 kayaks

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW LISTING ♥ Lake-House on Water, East Lake, Belgrade Lakes, holiday rental in Winslow
NEW LISTING ♥ Lake-House on Water, East Lake, Belgrade Lakes, holiday rental in Winslow
NEW LISTING ♥ Lake-House on Water, East Lake, Belgrade Lakes, holiday rental in Winslow

NEW LISTING ♥ Lake-House on Water, East Lake, Belgrade Lakes

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Lake Front with Amazing Sunsets on McGrath Pond, holiday rental in Winslow
Lake Front with Amazing Sunsets on McGrath Pond, holiday rental in Winslow
Lake Front with Amazing Sunsets on McGrath Pond, holiday rental in Winslow

Lake Front with Amazing Sunsets on McGrath Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing year round destination home, East Pond Oakland Maine, holiday rental in Winslow
Amazing year round destination home, East Pond Oakland Maine, holiday rental in Winslow
Amazing year round destination home, East Pond Oakland Maine, holiday rental in Winslow

Amazing year round destination home, East Pond Oakland Maine

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Listing! Lakeside Cabin Retreat w/Private Waterfront, Dock, Kayaks & More!, holiday rental in Winslow
New Listing! Lakeside Cabin Retreat w/Private Waterfront, Dock, Kayaks & More!, holiday rental in Winslow
New Listing! Lakeside Cabin Retreat w/Private Waterfront, Dock, Kayaks & More!, holiday rental in Winslow

New Listing! Lakeside Cabin Retreat w/Private Waterfront, Dock, Kayaks & More!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterville Home Rental w/ Private Yard + Deck!, holiday rental in Winslow
Waterville Home Rental w/ Private Yard + Deck!, holiday rental in Winslow
Waterville Home Rental w/ Private Yard + Deck!, holiday rental in Winslow

Waterville Home Rental w/ Private Yard + Deck!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Sidney Getaway w/ Private Dock!, holiday rental in Winslow
Waterfront Sidney Getaway w/ Private Dock!, holiday rental in Winslow
Waterfront Sidney Getaway w/ Private Dock!, holiday rental in Winslow

Waterfront Sidney Getaway w/ Private Dock!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Sunny, spacious and updated lake cottage - amazing views & steps from the water!, holiday rental in Winslow
Sunny, spacious and updated lake cottage - amazing views & steps from the water!, holiday rental in Winslow
Sunny, spacious and updated lake cottage - amazing views & steps from the water!, holiday rental in Winslow

Sunny, spacious and updated lake cottage - amazing views & steps from the water!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Lakefront home near Colby College and Thomas College, holiday rental in Winslow
Lakefront home near Colby College and Thomas College, holiday rental in Winslow
Lakefront home near Colby College and Thomas College, holiday rental in Winslow

Lakefront home near Colby College and Thomas College

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Sweet Retreat 1: 3 BDR Stylish & Cozy Min To Colby, holiday rental in Winslow
Sweet Retreat 1: 3 BDR Stylish & Cozy Min To Colby, holiday rental in Winslow
Sweet Retreat 1: 3 BDR Stylish & Cozy Min To Colby, holiday rental in Winslow

Sweet Retreat 1: 3 BDR Stylish & Cozy Min To Colby

Condo/Apartment
8 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Directly across the street from China Lake and boat launch, holiday rental in Winslow
Directly across the street from China Lake and boat launch, holiday rental in Winslow
Directly across the street from China Lake and boat launch, holiday rental in Winslow

Directly across the street from China Lake and boat launch

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Sweet Retreat 2: Stylish & Cozy Home Mins to Colby, holiday rental in Winslow
Sweet Retreat 2: Stylish & Cozy Home Mins to Colby, holiday rental in Winslow
Sweet Retreat 2: Stylish & Cozy Home Mins to Colby, holiday rental in Winslow

Sweet Retreat 2: Stylish & Cozy Home Mins to Colby

Condo/Apartment
7 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Winslow