Pines Cottage

8.8 / 10.0

Excellent(1,002 Ratings)

Microtel Inn & Suites By Wyndham Windham

Hotel

3star

2 guests · 1 bedroom · 1 bath

Pool · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Hotel in Windham has everything you need for a rejuvenating stay. Treat yourself to Microtel Inn & Suites By Wyndham Windham's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

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8.8 / 10.0

Excellent(1,013 Ratings)

Microtel Inn & Suites By Wyndham Windham

Hotel

3star

1 queen bed

Pool · Air conditioner · Internet / Wifi

Enjoy the best of Windham in our Hotel, Microtel Inn & Suites By Wyndham Windham. A stunning property with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

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10.0 / 10.0

Outstanding(68 Ratings)

Sunny Waterfront Family Friendly Little Sebago Home

16 guests · 5 bedrooms · 4 baths

Pets allowed · Kitchen or Kitchenette · Internet / Wifi

House in Windham, for $1,273 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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9.8 / 10.0

Outstanding(60 Ratings)

SEBAGO LAKE HOME WITH WALK OUT SANDY BEACH

12 guests · 5 bedrooms · 3 baths

Garden · Pool · Kitchen or Kitchenette

House in Windham, for $787 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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10.0 / 10.0

Outstanding(54 Ratings)

Simonson Lakeside 4 Bedrooms

in Falmouth

8 guests · 4 bedrooms · 3 baths

Kitchen or Kitchenette · Internet / Wifi · Parking

Are you ready to indulge in a relaxing getaway? Our House in Windham has everything you need for a rejuvenating stay. Treat yourself to Simonson Lakeside 4 Bedrooms's exceptional amenities, such as Dishwasher, Fireplace and Internet / Wifi.

$$$$

Beachfront

No ratings yet

JORDAN BAY GETAWAY LIMIT 8 home

in Standish

Pool · Kitchen or Kitchenette · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Windham, at $117 per night for your next great vacation.

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9.7 / 10.0

Outstanding(58 Ratings)

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

7 guests · 3 bedrooms · 2 baths

Garden · Pool · Kitchen or Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Windham, at $354 per night for your next great vacation.

$$$$

10.0 / 10.0

Outstanding(53 Ratings)

Steps from the beach on Sebago Lake Basin

6 guests · 2 bedrooms · 2 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Most favorited

This House for $536 in Windham, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

9.5 / 10.0

Outstanding(2 Ratings)

Overlook at Highland Lake

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This House for $115 in Windham, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

10.0 / 10.0

Outstanding(45 Ratings)

Authentic ME 4 BR log cabin on flat land, sandy beach, Little Sebago waterfront

Cabin

in Raymond

12 guests · 4 bedrooms · 2 baths

Garden · Kitchen or Kitchenette · Internet / Wifi

Looking to create some memories in Windham? Look no further than our Cabin, Authentic ME 4 BR log cabin on flat land, sandy beach, Little Sebago waterfront. Enjoy top-rated amenities including Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$

9.9 / 10.0

Outstanding(34 Ratings)

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

12 guests · 5 bedrooms · 4 baths

Garden · Pool · Kitchen or Kitchenette

Looking for a memorable stay in Windham? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$

No ratings yet

Cozy cottage

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our House in Windham has everything you need for a rejuvenating stay. Treat yourself to Cozy cottage's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

$$$$

9.6 / 10.0

Outstanding(31 Ratings)

Beautiful Lakefront Family Compound With Dock And Moorings: Stunning Sunsets!

14 guests · 7 bedrooms · 3 baths

Garden · Kitchen or Kitchenette · Air conditioner

House in Windham, for $952 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$

9.7 / 10.0

Outstanding(28 Ratings)

Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth

6 guests · 3 bedrooms · 2 baths

Garden · Pool · Kitchen or Kitchenette

Looking for a Cottage in Windham, this Cottage for $681 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$

9.3 / 10.0

Outstanding(7 Ratings)

And.N Bed & Breakfast

Bed and Breakfast

1 queen bed

Garden · Pets allowed · Air conditioner

Bed and Breakfast in Windham, for $108 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$

9.8 / 10.0

Outstanding(54 Ratings)

And. N B&B

Bed and Breakfast

2 guests · 1 bedroom · 1 bath

Garden · Air conditioner · Internet / Wifi

Looking for a memorable stay in Windham? Our Bed and Breakfast might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Parking, and more during your stay.

$$$$

9.6 / 10.0

Outstanding(54 Ratings)

And. N B&B

Bed and Breakfast

1 queen bed

Garden · Air conditioner · Internet / Wifi

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Windham, at $175 per night for your next great vacation.

$$$$

Start earning One Key rewards

9.8 / 10.0

Outstanding(28 Ratings)

Little Sebago Lakefront: Enjoy simple life & all year fun in SUMMER/FALL/WINTER!

8 guests · 2 bedrooms · 2 baths

Garden · Pool · Pets allowed

Discover the beauty of Windham with a stay at Little Sebago Lakefront: Enjoy simple life & all year fun in SUMMER/FALL/WINTER!, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

8.9 / 10.0

Excellent(39 Ratings)

Lakefront Cottage . Located 20 minutes from Portland

in Widham

6 guests · 2 bedrooms · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our Cottage in Windham has everything you need for a rejuvenating stay. Treat yourself to Lakefront Cottage . Located 20 minutes from Portland's exceptional amenities, such as Air conditioner, Fireplace and Internet / Wifi.

$$$$

9.6 / 10.0

Outstanding(28 Ratings)

Lakefront home with sunrise views, private dock, kayaks, paddle boards, WFH desk

6 guests · 3 bedrooms · 2 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience the best of Windham with this House available for $444. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$

No ratings yet

Waterfront Access with Kayaks Private Deck and a Firepit

Garden · Pets allowed · Kitchen or Kitchenette

The best choice in Windham for House, for $134 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

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Beach nearby, sun loungers, beach towels

10.0 / 10.0

Outstanding(23 Ratings)

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

Farm Stay

8 guests · 4 bedrooms · 2 baths

Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Windham with a stay at Family & dog friendly historic 4BR farmhouse near Sebago Lake w/ boat launch!, a top rated Farm Stay with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$

Start earning One Key rewards

8.4 / 10.0

Excellent(35 Ratings)

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Cabin

7 guests · 3 bedrooms · 2 baths

Garden · Pets allowed · Kitchen or Kitchenette

The best choice in Windham for Cabin, for $396 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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1.0 / 10.0

Terrible(1 Rating)

Highland Playhouse

Garden · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Windham at Highland Playhouse for $115 for your next trip.

$$$$

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9.6 / 10.0

Outstanding(24 Ratings)

BOOK NOW AND SAVE BIG FOR SUMMER 2025

12 guests · 5 bedrooms · 3 baths

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

When traveling to Windham, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $1,899 per night.

$$$$

10.0 / 10.0

Outstanding(21 Ratings)

Lakefront House

10 guests · 4 bedrooms · 2 baths

Garden · Pets allowed · Kitchen or Kitchenette

This inviting House in Windham can fit your needs for many types of vacations, at $1,152 per night.

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9.3 / 10.0

Outstanding(3 Ratings)

Loons Nest Cottage

in Standish

Pets allowed · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Windham? This House offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

9.9 / 10.0

Outstanding(20 Ratings)

Beautiful little camp (seasonal cottage) on Highland Lake in Falmouth, Maine.

in Falmouth

6 guests · 3 bedrooms · 1 bath

Garden · Kitchen or Kitchenette · Air conditioner

Experience vacation in Windham with our Cottage, Beautiful little camp (seasonal cottage) on Highland Lake in Falmouth, Maine.. Enjoy amenities such as Air conditioner, Fireplace and Internet / Wifi, and more.

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