House
10.0(64 Reviews)
2 Bedrooms
6 Guests
Parking
Ocean View
Balcony/Terrace
View
US $449/Night
7 Nights - US $3,144
Windham Holiday Rentals
We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Holiday Rentals, Villas & Resorts in Windham
10.0
House
9.5(4 Reviews)
2 Bedrooms
6 Guests
Breakfast- Parking
Skiing
Air Conditioner
US $312/Night
7 Nights - US $2,184
US $300/Night
7 Nights - US $2,098
Apartment
10.0(5 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $217/Night
7 Nights - US $1,522
US $141/Night
7 Nights - US $987
Apartment
10.0(4 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
Internet
Pet Friendly
US $506/Night
7 Nights - US $3,540
Cottage
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $221/Night
7 Nights - US $1,549
Cottage
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $472/Night
7 Nights - US $3,307
Cottage
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $243/Night
7 Nights - US $1,704
Luxury Holiday Rentals in Windham
Over 109+ Luxury Holiday Rentals in or Near Windham
House
10.0(66 Reviews)
4 Bedrooms
9 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,681/Night
7 Nights - US $11,765
House
9.8(27 Reviews)
5 Bedrooms
12 Guests
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $1,341/Night
7 Nights - US $9,387
House
10.0(85 Reviews)
5 Bedrooms
16 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,161/Night
7 Nights - US $8,127
New
Cottage
10.0(8 Reviews)
5 Bedrooms
12 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $1,104/Night
7 Nights - US $7,727
House
6 Bedrooms
12 Guests
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $1,078/Night
7 Nights - US $7,546
House
9.4(6 Reviews)
5 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $973/Night
7 Nights - US $6,814
House
9.6(13 Reviews)
4 Bedrooms
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $934/Night
7 Nights - US $6,535
House
9.4(17 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $799/Night
7 Nights - US $5,593
New
House
2 Bedrooms
11 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $765/Night
7 Nights - US $5,353
Top-Rated Holiday Rentals with a Pool in Windham
Over 3+ The Best Private Villas and Holiday Rentals in Windham with a Pool
Other
10.0(34 Reviews)
4 Bedrooms
8 Guests
- Parking
Pool- Ocean View
- Balcony/Terrace
US $458/Night
7 Nights - US $3,203
House
9.8(15 Reviews)
4 Bedrooms
10 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $728/Night
7 Nights - US $5,099
Pet-Friendly Holiday Rentals in Windham
Over 38+ Pet-Friendly Holiday Rentals in or Near Windham
Cottage
9.4(13 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $445/Night
7 Nights - US $3,117
US $540/Night
7 Nights - US $3,780
Cottage
8.0(1 Review)
2 Bedrooms
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $241/Night
7 Nights - US $1,684
US $391/Night
7 Nights - US $2,737
Cabin
7.6(7 Reviews)
2 Bedrooms
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $450/Night
7 Nights - US $3,147
House
10.0(42 Reviews)
4 Bedrooms
14 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $415/Night
7 Nights - US $2,907
Cabin
10.0(30 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $566/Night
7 Nights - US $3,965
House
10.0(27 Reviews)
6 Bedrooms
15 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $699/Night
7 Nights - US $4,891
House
10.0(4 Reviews)
4 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $643/Night
7 Nights - US $4,500
Large Holiday Rentals and Private Villas in Windham
Over 20+ Large Holiday Rentals and Private Villas in or Near Windham
House
10.0(5 Reviews)
3 Bedrooms
11 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $661/Night
7 Nights - US $4,625
US $407/Night
7 Nights - US $2,849
House
9.8(43 Reviews)
5 Bedrooms
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $750/Night
7 Nights - US $5,249
House
9.8(37 Reviews)
5 Bedrooms
14 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $702/Night
7 Nights - US $4,917
House
6 Bedrooms
12 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $654/Night
7 Nights - US $4,576
House
5 Bedrooms
10 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $537/Night
7 Nights - US $3,762
House
10.0(4 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $886/Night
7 Nights - US $6,203
Cottage
10.0(4 Reviews)
6 Bedrooms
11 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $409/Night
7 Nights - US $2,861
House
10.0(1 Review)
4 Bedrooms
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $709/Night
7 Nights - US $4,962
Windham Private Villas and Holiday Homes Under $200
Over 10+ Windham Private Villas and Holiday Homes Under $200
House
9.8(68 Reviews)
2 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $91/Night
7 Nights - US $635
US $106/Night
7 Nights - US $740
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $147/Night
7 Nights - US $1,030
US $54/Night
7 Nights - US $378
House
2 Bedrooms
6 Guests
- Parking
- Kitchen
- Internet
Bedding/Linens
US $190/Night
7 Nights - US $1,330
House
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $122/Night
7 Nights - US $854
Cottage
4.0(3 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $188/Night
7 Nights - US $1,316
Apartment
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pet Friendly
US $199/Night
7 Nights - US $1,393
House
3 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $150/Night
7 Nights - US $1,050
Instantly Bookable Holiday Homes in Windham
Over 39+ Instantly Bookable Holiday Homes in or Near Windham
House
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $747/Night
7 Nights - US $5,228
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $409/Night
7 Nights - US $2,860
Cabin
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Parking
- Kitchen
- Internet
- Laundry
US $470/Night
7 Nights - US $3,293
Cottage
9.8(73 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $353/Night
7 Nights - US $2,468
Cottage
9.4(6 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $296/Night
7 Nights - US $2,070
House
9.4(3 Reviews)
3 Bedrooms
8 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Pet Friendly
US $748/Night
7 Nights - US $5,234
Cabin
8.8(54 Reviews)
3 Bedrooms
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $369/Night
7 Nights - US $2,585
House
3 Bedrooms
- Internet
- Child Friendly
- Laundry
- Bedding/Linens
US $432/Night
7 Nights - US $3,026
New
Cottage
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $654/Night
7 Nights - US $4,575
Book a Last Minute Place to Stay in Windham
About Casai's Private Villas and Holiday Rentals in Windham
Discover more than 118 vacation rentals available in Windham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windham.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windham. On average, places to stay near Windham offer 650.08 ft², with nightly prices averaging US $462.
With Casai, finding and comparing holiday rentals in Windham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Windham, ME
There are 118 Windham, ME Holiday Rentals
- Prices for a holiday home in Windham start at US $54
- Top rated vacation home in Windham is Sunny Waterfront Family Friendly Little Sebago Home
- Most popular short term in Windham is Dormir
- Cheapest place to stay in Windham is Anglers apartment
- Most expensive holiday rental in Windham is SEBAGO LAKE HOME WITH 2 WALK OUT SANDY ASSOC BEACH
Recently Booked Holiday Rentals in Windham
Frequently Asked Questions About Windham?
What are the top holiday rentals in Windham?
With numerous options available in Windham, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windham:
- Sunny Waterfront Family Friendly Little Sebago Home
- SEBAGO LAKE HOME WITH 2 WALK OUT SANDY ASSOC BEACH
- Steps from the beach on Sebago Lake Basin
- Lakefront House
- Family & dog friendly historic 4BR farmhouse near Sebago Lake w/boat launch!
- Cozy Lakefront Cabin Portland - Windham area
- Cozy 100-year-old Maine camp, steps to Little Sebago Lake
- Rise & Shine - Breathtaking Sebago Lake view
- Rosebud on Little Sebago Lake
- Lakefront newly renovated 3-bedroom house with two Kitchens in tranquil Windham
Which holiday homes in Windham are best for families?
If you're searching for a family-friendly holiday home in Windham, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windham:
How many Casai.nz holiday rentals are available in Windham?
As of 2026, Casai boasts over 118 properties listed in the Windham area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windham.
