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Windham Vacation Rentals

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56 rentals in Windham.
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Sebago Lake... charming  2 bedroom  WATERFRONT cottage. Dock, mooring, & SUNSETS, vacation rental in Windham
Sebago Lake... charming  2 bedroom  WATERFRONT cottage. Dock, mooring, & SUNSETS, vacation rental in Windham
Sebago Lake... charming  2 bedroom  WATERFRONT cottage. Dock, mooring, & SUNSETS, vacation rental in Windham

Sebago Lake... charming 2 bedroom WATERFRONT cottage. Dock, mooring, & SUNSETS

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Family Reunion/ Retreat Home on Lake Sebago, vacation rental in Windham
Waterfront Family Reunion/ Retreat Home on Lake Sebago, vacation rental in Windham
Waterfront Family Reunion/ Retreat Home on Lake Sebago, vacation rental in Windham

Waterfront Family Reunion/ Retreat Home on Lake Sebago

Rental Home
9 bedrooms
10 bathrooms
Sleeps 22
Match: Sleeps
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Steps from the beach on Sebago Lake Basin, vacation rental in Windham
Steps from the beach on Sebago Lake Basin, vacation rental in Windham
Steps from the beach on Sebago Lake Basin, vacation rental in Windham

Steps from the beach on Sebago Lake Basin

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fun with Family and Friends, vacation rental in Windham
Fun with Family and Friends, vacation rental in Windham
Fun with Family and Friends, vacation rental in Windham

Fun with Family and Friends

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront home w/ private dock, kayaks, canoe & incredible views!, vacation rental in Windham
Lakefront home w/ private dock, kayaks, canoe & incredible views!, vacation rental in Windham
Lakefront home w/ private dock, kayaks, canoe & incredible views!, vacation rental in Windham

Lakefront home w/ private dock, kayaks, canoe & incredible views!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sunny Waterfront Family Friendly Little Sebago Home, vacation rental in Windham
Sunny Waterfront Family Friendly Little Sebago Home, vacation rental in Windham
Sunny Waterfront Family Friendly Little Sebago Home, vacation rental in Windham

Sunny Waterfront Family Friendly Little Sebago Home

Rental Home
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Cozy Year-round House right outside Portland Maine on Highland Lake., vacation rental in Windham
Cozy Year-round House right outside Portland Maine on Highland Lake., vacation rental in Windham
Cozy Year-round House right outside Portland Maine on Highland Lake., vacation rental in Windham

Cozy Year-round House right outside Portland Maine on Highland Lake.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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100 ft of lake front, Little Sebago Lake, Maine, vacation rental in Windham
100 ft of lake front, Little Sebago Lake, Maine, vacation rental in Windham
100 ft of lake front, Little Sebago Lake, Maine, vacation rental in Windham

100 ft of lake front, Little Sebago Lake, Maine

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Sebago Lake Getaway, vacation rental in Windham
Charming Sebago Lake Getaway, vacation rental in Windham
Charming Sebago Lake Getaway, vacation rental in Windham

Charming Sebago Lake Getaway

Rental Home
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth, vacation rental in Windham
Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth, vacation rental in Windham
Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth, vacation rental in Windham

Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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6 Bdrm Little Sebago Lakefront Home - Sandy Beach, Amazing Sunsets, New kitchen!, vacation rental in Windham
6 Bdrm Little Sebago Lakefront Home - Sandy Beach, Amazing Sunsets, New kitchen!, vacation rental in Windham
6 Bdrm Little Sebago Lakefront Home - Sandy Beach, Amazing Sunsets, New kitchen!, vacation rental in Windham

6 Bdrm Little Sebago Lakefront Home - Sandy Beach, Amazing Sunsets, New kitchen!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Beautiful new  home in the gateway to the lake region!, vacation rental in Windham
Beautiful new  home in the gateway to the lake region!, vacation rental in Windham
Beautiful new  home in the gateway to the lake region!, vacation rental in Windham

Beautiful new home in the gateway to the lake region!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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JUNE 24 -JULY 1st SILL AVAILABLE !!, vacation rental in Windham
JUNE 24 -JULY 1st SILL AVAILABLE !!, vacation rental in Windham
JUNE 24 -JULY 1st SILL AVAILABLE !!, vacation rental in Windham

JUNE 24 -JULY 1st SILL AVAILABLE !!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Sprawling Sebago Lake Estate, vacation rental in Windham
Sprawling Sebago Lake Estate, vacation rental in Windham
Sprawling Sebago Lake Estate, vacation rental in Windham

Sprawling Sebago Lake Estate

Rental Home
6 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Frye Island Waterfront House - Large Private Beach With Beautiful Sunset Views., vacation rental in Windham
Frye Island Waterfront House - Large Private Beach With Beautiful Sunset Views., vacation rental in Windham
Frye Island Waterfront House - Large Private Beach With Beautiful Sunset Views., vacation rental in Windham

Frye Island Waterfront House - Large Private Beach With Beautiful Sunset Views.

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Lake Front Cottage with Private Sandy Beach & Beautiful Sunsets, vacation rental in Windham
Lake Front Cottage with Private Sandy Beach & Beautiful Sunsets, vacation rental in Windham
Lake Front Cottage with Private Sandy Beach & Beautiful Sunsets, vacation rental in Windham

Lake Front Cottage with Private Sandy Beach & Beautiful Sunsets

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Breathtaking Lake Views, vacation rental in Windham
Breathtaking Lake Views, vacation rental in Windham
Breathtaking Lake Views, vacation rental in Windham

Breathtaking Lake Views

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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2300 SF, 3 Bdrm, 3.5 Bath Vacation Home Steps from Highland Lake, vacation rental in Windham
2300 SF, 3 Bdrm, 3.5 Bath Vacation Home Steps from Highland Lake, vacation rental in Windham
2300 SF, 3 Bdrm, 3.5 Bath Vacation Home Steps from Highland Lake, vacation rental in Windham

2300 SF, 3 Bdrm, 3.5 Bath Vacation Home Steps from Highland Lake

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Planning a Classic Maine Vacation?  This is the house for you!, vacation rental in Windham
Planning a Classic Maine Vacation?  This is the house for you!, vacation rental in Windham
Planning a Classic Maine Vacation?  This is the house for you!, vacation rental in Windham

Planning a Classic Maine Vacation? This is the house for you!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WEST SIDE WATER VIEW,SUNSETS, SCREENED PORCH, POOL TABLE, SPACIUOS, vacation rental in Windham
WEST SIDE WATER VIEW,SUNSETS, SCREENED PORCH, POOL TABLE, SPACIUOS, vacation rental in Windham
WEST SIDE WATER VIEW,SUNSETS, SCREENED PORCH, POOL TABLE, SPACIUOS, vacation rental in Windham

WEST SIDE WATER VIEW,SUNSETS, SCREENED PORCH, POOL TABLE, SPACIUOS

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!, vacation rental in Windham
Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!, vacation rental in Windham
Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!, vacation rental in Windham

Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sebago Lake Home with Mountain & Lake Views, vacation rental in Windham
Sebago Lake Home with Mountain & Lake Views, vacation rental in Windham
Sebago Lake Home with Mountain & Lake Views, vacation rental in Windham

Sebago Lake Home with Mountain & Lake Views

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Highland Lake Front Cottage, vacation rental in Windham
Highland Lake Front Cottage, vacation rental in Windham
Highland Lake Front Cottage, vacation rental in Windham

Highland Lake Front Cottage

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Paradise on Sebago Lake, vacation rental in Windham
Paradise on Sebago Lake, vacation rental in Windham
Paradise on Sebago Lake, vacation rental in Windham

Paradise on Sebago Lake

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Planning a Classic Maine Vacation?  This is the house for you!, vacation rental in Windham
Planning a Classic Maine Vacation?  This is the house for you!, vacation rental in Windham
Planning a Classic Maine Vacation?  This is the house for you!, vacation rental in Windham

Planning a Classic Maine Vacation? This is the house for you!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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6 bedroom waterfront cabin -enjoy beautiful sunsets!, vacation rental in Windham
6 bedroom waterfront cabin -enjoy beautiful sunsets!, vacation rental in Windham
6 bedroom waterfront cabin -enjoy beautiful sunsets!, vacation rental in Windham

6 bedroom waterfront cabin -enjoy beautiful sunsets!

Rental Home
6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Lakefront  Cabin Portland - Windham Area, vacation rental in Windham
Cozy Lakefront  Cabin Portland - Windham Area, vacation rental in Windham
Cozy Lakefront  Cabin Portland - Windham Area, vacation rental in Windham

Cozy Lakefront Cabin Portland - Windham Area

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront cabin on beautiful Sebago Lake, vacation rental in Windham
Waterfront cabin on beautiful Sebago Lake, vacation rental in Windham
Waterfront cabin on beautiful Sebago Lake, vacation rental in Windham

Waterfront cabin on beautiful Sebago Lake

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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K2 Lake Paradise, vacation rental in Windham
K2 Lake Paradise, vacation rental in Windham
K2 Lake Paradise, vacation rental in Windham

K2 Lake Paradise

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Lake View Lodge, vacation rental in Windham
Lake View Lodge, vacation rental in Windham
Lake View Lodge, vacation rental in Windham

Lake View Lodge

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage with Screened Deck, Great Lake View, WiFi & Shared Firepit!, vacation rental in Windham
Lakefront Cottage with Screened Deck, Great Lake View, WiFi & Shared Firepit!, vacation rental in Windham
Lakefront Cottage with Screened Deck, Great Lake View, WiFi & Shared Firepit!, vacation rental in Windham

Lakefront Cottage with Screened Deck, Great Lake View, WiFi & Shared Firepit!

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Peaceful House on Sebago Lake, vacation rental in Windham
Peaceful House on Sebago Lake, vacation rental in Windham
Peaceful House on Sebago Lake, vacation rental in Windham

Peaceful House on Sebago Lake

Rental Home
6 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Lakefront house located on Little Sebago lake ~ 2,500 Sf. Ft., vacation rental in Windham
Lakefront house located on Little Sebago lake ~ 2,500 Sf. Ft., vacation rental in Windham
Lakefront house located on Little Sebago lake ~ 2,500 Sf. Ft., vacation rental in Windham

Lakefront house located on Little Sebago lake ~ 2,500 Sf. Ft.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Your home away from home - cozy cabin on Sebago Lake in quiet Jordan Bay region, vacation rental in Windham
Your home away from home - cozy cabin on Sebago Lake in quiet Jordan Bay region, vacation rental in Windham
Your home away from home - cozy cabin on Sebago Lake in quiet Jordan Bay region, vacation rental in Windham

Your home away from home - cozy cabin on Sebago Lake in quiet Jordan Bay region

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Lakefront Family Compound With Dock And Moorings: Stunning Sunsets!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Lake View Lodge Unit #2 Can be rented w/ Unit # 1, vacation rental in Windham
Lake View Lodge Unit #2 Can be rented w/ Unit # 1, vacation rental in Windham
Lake View Lodge Unit #2 Can be rented w/ Unit # 1, vacation rental in Windham

Lake View Lodge Unit #2 Can be rented w/ Unit # 1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Lakefront Home-Hot Tub-Great for Families-Large Yard-Quiet-Shallow Entry, vacation rental in Windham
Private Lakefront Home-Hot Tub-Great for Families-Large Yard-Quiet-Shallow Entry, vacation rental in Windham
Private Lakefront Home-Hot Tub-Great for Families-Large Yard-Quiet-Shallow Entry, vacation rental in Windham

Private Lakefront Home-Hot Tub-Great for Families-Large Yard-Quiet-Shallow Entry

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Frye Island Paradise - Renovated cabin on Sebago Lake - Just a ferry ride away, vacation rental in Windham
Frye Island Paradise - Renovated cabin on Sebago Lake - Just a ferry ride away, vacation rental in Windham
Frye Island Paradise - Renovated cabin on Sebago Lake - Just a ferry ride away, vacation rental in Windham

Frye Island Paradise - Renovated cabin on Sebago Lake - Just a ferry ride away

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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Frye Island - Sebago Lake Waterfront Rental, vacation rental in Windham
Frye Island - Sebago Lake Waterfront Rental, vacation rental in Windham
Frye Island - Sebago Lake Waterfront Rental, vacation rental in Windham

Frye Island - Sebago Lake Waterfront Rental

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun, vacation rental in Windham
Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun, vacation rental in Windham
Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun, vacation rental in Windham

Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Waterfront Retreat - Large Deck, Close to Portland, vacation rental in Windham
Cozy Waterfront Retreat - Large Deck, Close to Portland, vacation rental in Windham
Cozy Waterfront Retreat - Large Deck, Close to Portland, vacation rental in Windham

Cozy Waterfront Retreat - Large Deck, Close to Portland

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful Waterfront Hideaway with 5 bedrooms!, vacation rental in Windham
Peaceful Waterfront Hideaway with 5 bedrooms!, vacation rental in Windham
Peaceful Waterfront Hideaway with 5 bedrooms!, vacation rental in Windham

Peaceful Waterfront Hideaway with 5 bedrooms!

Rental Home
5 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy 100-year-old Maine camp, steps to Little Sebago Lake, vacation rental in Windham
Cozy 100-year-old Maine camp, steps to Little Sebago Lake, vacation rental in Windham
Cozy 100-year-old Maine camp, steps to Little Sebago Lake, vacation rental in Windham

Cozy 100-year-old Maine camp, steps to Little Sebago Lake

Rental Home
4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Large Lake Access Home Close to Portland, vacation rental in Windham
Large Lake Access Home Close to Portland, vacation rental in Windham
Large Lake Access Home Close to Portland, vacation rental in Windham

Large Lake Access Home Close to Portland

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Cape-Mountain Views & Sebago Lake Access, vacation rental in Windham
Spacious Cape-Mountain Views & Sebago Lake Access, vacation rental in Windham
Spacious Cape-Mountain Views & Sebago Lake Access, vacation rental in Windham

Spacious Cape-Mountain Views & Sebago Lake Access

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakeside Retreat on Big Sebago with Mountain Views, vacation rental in Windham
Lakeside Retreat on Big Sebago with Mountain Views, vacation rental in Windham
Lakeside Retreat on Big Sebago with Mountain Views, vacation rental in Windham

Lakeside Retreat on Big Sebago with Mountain Views

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lake home Paradise, vacation rental in Windham
Lake home Paradise, vacation rental in Windham
Lake home Paradise, vacation rental in Windham

Lake home Paradise

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern camper getaway, in the Sebago Lakes Region!, vacation rental in Windham
Modern camper getaway, in the Sebago Lakes Region!, vacation rental in Windham
Modern camper getaway, in the Sebago Lakes Region!, vacation rental in Windham

Modern camper getaway, in the Sebago Lakes Region!

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Highland Lake House, vacation rental in Windham
Highland Lake House, vacation rental in Windham
Highland Lake House, vacation rental in Windham

Highland Lake House

Rental Home
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Shorefront on Sebago Lake.  Private Sandy Beach, vacation rental in Windham
Shorefront on Sebago Lake.  Private Sandy Beach, vacation rental in Windham
Shorefront on Sebago Lake.  Private Sandy Beach, vacation rental in Windham

Shorefront on Sebago Lake. Private Sandy Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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