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Winslow Holiday Rentals

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50 rentals in Winslow.
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Loon Loft on Pattee's Pond - Kayaks & Canoes - Fall 2020 Dates Available, holiday rental in Winslow
Loon Loft on Pattee's Pond - Kayaks & Canoes - Fall 2020 Dates Available, holiday rental in Winslow
Loon Loft on Pattee's Pond - Kayaks & Canoes - Fall 2020 Dates Available, holiday rental in Winslow

Loon Loft on Pattee's Pond - Kayaks & Canoes - Fall 2020 Dates Available

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Immaculate View On Webber Pond With Boat Rental Option, holiday rental in Winslow
Immaculate View On Webber Pond With Boat Rental Option, holiday rental in Winslow
Immaculate View On Webber Pond With Boat Rental Option, holiday rental in Winslow

Immaculate View On Webber Pond With Boat Rental Option

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home, holiday rental in Winslow
Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home, holiday rental in Winslow
Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home, holiday rental in Winslow

Teaberry Cottage! Quiet Setting On The Lake, All The Modern Comforts Of Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
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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Clean, new Eco-friendly Camp: Hidden Treasure on Golden Pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakeside house on Webber Pond with small beach and wonderful views.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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3 Bedroom year round lakefront home on Three Mile Pond in South China, ME

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Luxury Family Home / Retreat Center on Great Pond, holiday rental in Winslow
Luxury Family Home / Retreat Center on Great Pond, holiday rental in Winslow
Luxury Family Home / Retreat Center on Great Pond, holiday rental in Winslow

Luxury Family Home / Retreat Center on Great Pond

Holiday Rental House
7 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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Peaceful, Private Cottage on Lovejoy Pond, near Unity, with A/C, WiFi, kayak, holiday rental in Winslow
Peaceful, Private Cottage on Lovejoy Pond, near Unity, with A/C, WiFi, kayak, holiday rental in Winslow
Peaceful, Private Cottage on Lovejoy Pond, near Unity, with A/C, WiFi, kayak, holiday rental in Winslow

Peaceful, Private Cottage on Lovejoy Pond, near Unity, with A/C, WiFi, kayak

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Updated Oakland Cottage w/Deck on McGrath Pond!, holiday rental in Winslow
Updated Oakland Cottage w/Deck on McGrath Pond!, holiday rental in Winslow
Updated Oakland Cottage w/Deck on McGrath Pond!, holiday rental in Winslow

Updated Oakland Cottage w/Deck on McGrath Pond!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Webber Pond Lakefront Cottage - 2 bed, 1 bath, holiday rental in Winslow
Beautiful Webber Pond Lakefront Cottage - 2 bed, 1 bath, holiday rental in Winslow
Beautiful Webber Pond Lakefront Cottage - 2 bed, 1 bath, holiday rental in Winslow

Beautiful Webber Pond Lakefront Cottage - 2 bed, 1 bath

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Majestic View On Webber Pond With Boat Rental Option, holiday rental in Winslow
Majestic View On Webber Pond With Boat Rental Option, holiday rental in Winslow
Majestic View On Webber Pond With Boat Rental Option, holiday rental in Winslow

Majestic View On Webber Pond With Boat Rental Option

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Classic and adorable Maine camp on North Pond in the Belgrade Lakes, holiday rental in Winslow
Classic and adorable Maine camp on North Pond in the Belgrade Lakes, holiday rental in Winslow
Classic and adorable Maine camp on North Pond in the Belgrade Lakes, holiday rental in Winslow

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beautifully renovated cottage on quiet lake, holiday rental in Winslow
Beautifully renovated cottage on quiet lake, holiday rental in Winslow
Beautifully renovated cottage on quiet lake, holiday rental in Winslow

Beautifully renovated cottage on quiet lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The WATERFALL COTTAGE:  Best fishing, sunsets & only steps from quaint town., holiday rental in Winslow
The WATERFALL COTTAGE:  Best fishing, sunsets & only steps from quaint town., holiday rental in Winslow
The WATERFALL COTTAGE:  Best fishing, sunsets & only steps from quaint town., holiday rental in Winslow

The WATERFALL COTTAGE: Best fishing, sunsets & only steps from quaint town.

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 7
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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Picturesque Lakefront Retreat in Belgrade Lakes, holiday rental in Winslow
Picturesque Lakefront Retreat in Belgrade Lakes, holiday rental in Winslow
Picturesque Lakefront Retreat in Belgrade Lakes, holiday rental in Winslow

Picturesque Lakefront Retreat in Belgrade Lakes

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Maine Cabin on the Water, holiday rental in Winslow
Maine Cabin on the Water, holiday rental in Winslow
Maine Cabin on the Water, holiday rental in Winslow

Maine Cabin on the Water

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Lake Front Chalet on Great Pond, holiday rental in Winslow
Lake Front Chalet on Great Pond, holiday rental in Winslow
Lake Front Chalet on Great Pond, holiday rental in Winslow

Lake Front Chalet on Great Pond

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region, holiday rental in Winslow
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region, holiday rental in Winslow
Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region, holiday rental in Winslow

Timeless Lakefront Cottage with private dock- East Pond Belgrade Lakes Region

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Cottage With Double Decks On The Water And Incredible 180 Degree View, holiday rental in Winslow
Beautiful Cottage With Double Decks On The Water And Incredible 180 Degree View, holiday rental in Winslow
Beautiful Cottage With Double Decks On The Water And Incredible 180 Degree View, holiday rental in Winslow

Beautiful Cottage With Double Decks On The Water And Incredible 180 Degree View

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Camp Betty' Lakeside Retreat, holiday rental in Winslow
Camp Betty' Lakeside Retreat, holiday rental in Winslow
Camp Betty' Lakeside Retreat, holiday rental in Winslow

Camp Betty' Lakeside Retreat

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Little Beans Cottage, holiday rental in Winslow
Little Beans Cottage, holiday rental in Winslow
Little Beans Cottage, holiday rental in Winslow

Little Beans Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Under construction Lakefront home near Colby College, holiday rental in Winslow
Under construction Lakefront home near Colby College, holiday rental in Winslow
Under construction Lakefront home near Colby College, holiday rental in Winslow

Under construction Lakefront home near Colby College

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Twin Oaks on Great Pond, holiday rental in Winslow
Twin Oaks on Great Pond, holiday rental in Winslow
Twin Oaks on Great Pond, holiday rental in Winslow

Twin Oaks on Great Pond

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
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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'Not-A-Pine Lane COTTAGE' is a family treasure enjoyed generations, holiday rental in Winslow
'Not-A-Pine Lane COTTAGE' is a family treasure enjoyed generations, holiday rental in Winslow
'Not-A-Pine Lane COTTAGE' is a family treasure enjoyed generations, holiday rental in Winslow

'Not-A-Pine Lane COTTAGE' is a family treasure enjoyed generations

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Afterglow Cottage on Great Pond, holiday rental in Winslow
Afterglow Cottage on Great Pond, holiday rental in Winslow
Afterglow Cottage on Great Pond, holiday rental in Winslow

Afterglow Cottage on Great Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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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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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Great Pond Waterfront: Dog-friendly Home Near Colby College, holiday rental in Winslow
Great Pond Waterfront: Dog-friendly Home Near Colby College, holiday rental in Winslow
Great Pond Waterfront: Dog-friendly Home Near Colby College, holiday rental in Winslow

Great Pond Waterfront: Dog-friendly Home Near Colby College

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Pond- Rustic, charming Log Cabin, holiday rental in Winslow
Great Pond- Rustic, charming Log Cabin, holiday rental in Winslow
Great Pond- Rustic, charming Log Cabin, holiday rental in Winslow

Great Pond- Rustic, charming Log Cabin

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming waterfront studio in Belgrade, Maine!, holiday rental in Winslow
Charming waterfront studio in Belgrade, Maine!, holiday rental in Winslow
Charming waterfront studio in Belgrade, Maine!, holiday rental in Winslow

Charming waterfront studio in Belgrade, Maine!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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 Sunset (McGrath Pond), holiday rental in Winslow
Lake Front with Amazing Sunset (McGrath Pond), holiday rental in Winslow
Lake Front with Amazing Sunset (McGrath Pond), holiday rental in Winslow

Lake Front with Amazing Sunset (McGrath Pond)

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Pond Shoreline- Charming Log Cabin, holiday rental in Winslow
Great Pond Shoreline- Charming Log Cabin, holiday rental in Winslow
Great Pond Shoreline- Charming Log Cabin, holiday rental in Winslow

Great Pond Shoreline- Charming Log Cabin

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet Lakefront Camp, holiday rental in Winslow
Quiet Lakefront Camp, holiday rental in Winslow
Quiet Lakefront Camp, holiday rental in Winslow

Quiet Lakefront Camp

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Large New Rustic Cottage with Central a/c, holiday rental in Winslow
Large New Rustic Cottage with Central a/c, holiday rental in Winslow
Large New Rustic Cottage with Central a/c, holiday rental in Winslow

Large New Rustic Cottage with Central a/c

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
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Front Enclosed Screen Porch Facing Lake Has A See Thru Roof, holiday rental in Winslow
Front Enclosed Screen Porch Facing Lake Has A See Thru Roof, holiday rental in Winslow
Front Enclosed Screen Porch Facing Lake Has A See Thru Roof, holiday rental in Winslow

Front Enclosed Screen Porch Facing Lake Has A See Thru Roof

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious New Modern Home, holiday rental in Winslow
Spacious New Modern Home, holiday rental in Winslow
Spacious New Modern Home, holiday rental in Winslow

Spacious New Modern Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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BELGRADE LAKES  MAINE ** GREAT POND **  2 BEDROOM COTTAGE 15 FEET FROM WATER, holiday rental in Winslow
BELGRADE LAKES  MAINE ** GREAT POND **  2 BEDROOM COTTAGE 15 FEET FROM WATER, holiday rental in Winslow
BELGRADE LAKES  MAINE ** GREAT POND **  2 BEDROOM COTTAGE 15 FEET FROM WATER, holiday rental in Winslow

BELGRADE LAKES MAINE ** GREAT POND ** 2 BEDROOM COTTAGE 15 FEET FROM WATER

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New to the rental market! Lakefront Summer House on Webber Pond, holiday rental in Winslow
New to the rental market! Lakefront Summer House on Webber Pond, holiday rental in Winslow
New to the rental market! Lakefront Summer House on Webber Pond, holiday rental in Winslow

New to the rental market! Lakefront Summer House on Webber Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home, Sandy Beach, Belgrade Lakes Maine, holiday rental in Winslow
Waterfront Home, Sandy Beach, Belgrade Lakes Maine, holiday rental in Winslow
Waterfront Home, Sandy Beach, Belgrade Lakes Maine, holiday rental in Winslow

Waterfront Home, Sandy Beach, Belgrade Lakes Maine

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Star Point on Snow Pond in the Belgrade Lakes, holiday rental in Winslow
Star Point on Snow Pond in the Belgrade Lakes, holiday rental in Winslow
Star Point on Snow Pond in the Belgrade Lakes, holiday rental in Winslow

Star Point on Snow Pond in the Belgrade Lakes

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Home on Great Pond, holiday rental in Winslow
Waterfront Home on Great Pond, holiday rental in Winslow
Waterfront Home on Great Pond, holiday rental in Winslow

Waterfront Home on Great Pond

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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an apartment in rural maine, holiday rental in Winslow
an apartment in rural maine, holiday rental in Winslow
an apartment in rural maine, holiday rental in Winslow

an apartment in rural maine

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Great Pond Lake House, holiday rental in Winslow
Great Pond Lake House, holiday rental in Winslow
Great Pond Lake House, holiday rental in Winslow

Great Pond Lake House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Pond Waterfront: Spacious, Dog-friendly Home, Near Colby College, holiday rental in Winslow
Great Pond Waterfront: Spacious, Dog-friendly Home, Near Colby College, holiday rental in Winslow
Great Pond Waterfront: Spacious, Dog-friendly Home, Near Colby College, holiday rental in Winslow

Great Pond Waterfront: Spacious, Dog-friendly Home, Near Colby College

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lakeside Cottage with Hot tub in Belgrade Lakes, holiday rental in Winslow
Lakeside Cottage with Hot tub in Belgrade Lakes, holiday rental in Winslow
Lakeside Cottage with Hot tub in Belgrade Lakes, holiday rental in Winslow

Lakeside Cottage with Hot tub in Belgrade Lakes

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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