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Holiday homes in Windham You’ll Love

Top-Rated Windham Holiday homes for Every Budget and Style!

Looking for a holiday home in Windham (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Windham.

We found 39 Holiday-homes in Windham and the surrounding area (within 20 miles)

Snow Nirvana in Hunter, USA

Snow Nirvana

Villa in Hunter near Windham, Florida , 34 Eagles Nest Road
11 miles from Catskill State Park in Hunter, Snow Nirvana features accommodations with access to a sauna and hot tub.
  • Parking
  • Pets allowed
  • Bar
  • Sauna
  • Family rooms

no reviews

from $68.00 Show details »

Hunter Hideaway with Yard and Deck 3 Mi to Ski Slopes in Hunter, USA

Hunter Hideaway with Yard and Deck 3 Mi...

Holiday home in Hunter near Windham, Florida
Hunter Hideaway with Yard and Deck 3 Mi to Ski Slopes offers accommodations in Hunter, 29 miles from Hudson Athens Lighthouse and 2.8 miles from Hunte...
  • Parking
  • Spa and wellness centre

Fabulous 3 Reviews 9.0

from $346.68 Show details »

Charming Home with Majestic View in Hunter, USA

Charming Home with Majestic View

Holiday home in Hunter near Windham, Florida , 8741 New York 23A
Charming Home with Majestic View is located in Hunter, just 28 miles from Hudson Athens Lighthouse and 3.3 miles from Hunter Mountain.

Exceptional 1 Reviews 10.0

from $294.05 Show details »

Hunter Mt Amazing Views Catskills! 5 Bedrooms! Best Choice! in Hunter, USA

Hunter Mt Amazing Views Catskills! 5 Bed...

Holiday home in Hunter near Windham, Florida , 26 Ford Hill Road
Hunter Mt Amazing Views Catskills! 5 Bedrooms!
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 2 Reviews 10.0

from $472.40 Show details »

Stream-Side Atrium Home with Side Rooms & Pool Table in Hunter, USA

Stream-Side Atrium Home with Side Rooms...

Holiday home in Hunter near Windham, Florida , 10019 New York 23A
Stream-Side Atrium Home with Side Rooms & Pool Table is located in Hunter, just 6.4 miles from Hunter Mountain and 28 miles from Delaware Ulster Railr...
  • Pets allowed

Passable 1 Reviews 5.0

from $1.177.68 Show details »

Beautiful mountain home with gorgeous meadow views in Hunter, USA

Beautiful mountain home with gorgeous me...

Holiday home in Hunter near Windham, Florida , 71 Lawrence Road
Beautiful mountain home with gorgeous meadow views offers accommodations in Hunter, 5.7 miles from Hunter Mountain.
  • Parking
  • Family rooms

Passable 2 Reviews 5.5

from $433.95 Show details »

Maplewood Manor 8BR, Hot Tub, Gym, Fire Pit in Jewett, USA

Maplewood Manor 8BR, Hot Tub, Gym, Fire...

Holiday home in Jewett near Windham, Florida , 3913 County Road 23C
Maplewood Manor 8BR, Hot Tub, Gym, Fire Pit is a recently renovated vacation home in Jewett where guests can make the most of the garden and terrace.
  • Parking
  • Family rooms

Very good 2 Reviews 8.5

from $957.56 Show details »

Private Retreat Minutes from Town & Both Mountains in Jewett, USA

Private Retreat Minutes from Town & Both...

Holiday home in Jewett near Windham, Florida , 10 Tahoe Road
Private Retreat Minutes from Town & Both Mountains offers accommodations in Jewett, 6.7 miles from Hunter Mountain.
  • Pets allowed

Exceptional 1 Reviews 10.0

from $56.00 Show details »

Jewett Cabin with Viewing Deck - 10 Mins to Skiing! in Jewett, USA

Jewett Cabin with Viewing Deck - 10 Mins...

Holiday home in Jewett near Windham, Florida
Jewett Cabin with Viewing Deck - 10 Mins to Skiing! offers accommodations in Jewett, 6.8 miles from Hunter Mountain.
  • Parking

Very good 1 Reviews 8.0

from $264.57 Show details »

Dog-Friendly Mountain Hideaway in Jewett, USA

Dog-Friendly Mountain Hideaway

Holiday home in Jewett near Windham, Florida , 4513 County Road 23C
Dog-Friendly Mountain Hideaway offers accommodations in Jewett, 31 miles from Delaware Ulster Railroad.
  • Parking
  • Pets allowed

Fabulous 1 Reviews 9.0

from $439.47 Show details »

Country Escape Overlooking Hunter & Windham Mts in Jewett, USA

Country Escape Overlooking Hunter & Wind...

Holiday home in Jewett near Windham, Florida , 124 Acorn Drive
Country Escape Overlooking Hunter & Windham Mts offers accommodations in Jewett, 30 miles from Hudson Athens Lighthouse and 7.1 miles from Hunter Moun...
  • Parking
  • Pets allowed

no reviews

from $1.028.58 Show details »

Private 7-Acre Retreat On-Site Pond, Streams in Jewett, USA

Private 7-Acre Retreat On-Site Pond, Str...

Holiday home in Jewett near Windham, Florida
Private 7-Acre Retreat On-Site Pond, Streams offers accommodations in Jewett, 10 miles from Hunter Mountain and 30 miles from Delaware Ulster Railroad...
  • Parking
  • Pets allowed
  • Spa and wellness centre

Exceptional 1 Reviews 10.0

from $311.35 Show details »

CreeksideHome, 2-5min to Ski,Hiking,Lake,Cafe&Bars in Windham, USA

CreeksideHome, 2-5min to Ski,Hiking,Lake...

Holiday home in Windham, Florida , 14 Maplecrest Road
Providing a garden, CreeksideHome, 2-5min to Ski, Hiking,Lake,Cafe&Bars provides accommodations in Windham.
  • Parking
  • Pets allowed

no reviews

from $58.00 Show details »

Immaculate Windham Getaway Near Skiing and Hiking! in Windham, USA

Immaculate Windham Getaway Near Skiing a...

Holiday home in Windham, Florida
Immaculate Windham Getaway Near Skiing and Hiking! offers accommodations in Windham, 7.2 miles from Catskill State Park and 29 miles from Hudson Athen...
  • Parking

Exceptional 2 Reviews 10.0

from $352.80 Show details »

Chalet, New Hot Tub, 5 min to Windham skiing in Hensonville, USA

Chalet, New Hot Tub, 5 min to Windham sk...

Holiday home in Hensonville near Windham, Florida , 26 Albert Court
Chalet, New Hot Tub, 5 min to Windham skiing offers accommodations in Hensonville, 6.9 miles from Catskill State Park and 29 miles from Hudson Athens ...
  • Parking

no reviews

from $66.00 Show details »

Katskill Chalet Renovated with Endless View in Windham, USA

Katskill Chalet Renovated with Endless V...

Holiday home in Windham, Florida , 12 Reservoir Road
Featuring a garden, Katskill Chalet Renovated with Endless View features accommodations in Windham.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $66.00 Show details »

Mountain Lodge with Hot Tub & Fire Pit in Hensonville, USA

Mountain Lodge with Hot Tub & Fire Pit

Holiday home in Hensonville near Windham, Florida , 30 Chase Drive
Mountain Lodge with Hot Tub & Fire Pit offers accommodations in Hensonville, 28 miles from Hudson Athens Lighthouse and 9 miles from Hunter Mountain.

no reviews

from $59.00 Show details »

Retro Retreat Charming Home with Hot Tub & Fire Pit in Hensonville, USA

Retro Retreat Charming Home with Hot Tub...

Holiday home in Hensonville near Windham, Florida , 29 Chase Drive
Featuring a garden, Retro Retreat Charming Home with Hot Tub & Fire Pit offers accommodations in Hensonville.

no reviews

from $246.37 Show details »

Relaxation Retreat Home with Hot Tub Gym & Sauna in Prattsville, USA

Relaxation Retreat Home with Hot Tub Gym...

Holiday home in Prattsville near Windham, Florida , 12658 New York 23
15 miles from Catskill State Park in Prattsville, Relaxation Retreat Home with Hot Tub Gym & Sauna features accommodations with access to a fitness ce...
  • Fitness centre

no reviews

from $312.68 Show details »

Experience the Wonder of Windham in Windham, USA

Experience the Wonder of Windham

Holiday home in Windham, Florida , 11320 New York 23
Experience the Wonder of Windham offers accommodations in Windham, 11 miles from Hunter Mountain.
  • Pets allowed

no reviews

from $52.00 Show details »

Redwood Retreat in Windham - Pickleball! Tennis! in Windham, USA

Redwood Retreat in Windham - Pickleball!...

Holiday home in Windham, Florida , 44 Quads Way
Redwood Retreat in Windham - Pickleball!
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 22 Reviews 9.4

from $165.77 Show details »

Slope Views Luxe Windham Retreat with Hot Tub! in Windham, USA

Slope Views Luxe Windham Retreat with Ho...

Holiday home in Windham, Florida
Slope Views Luxe Windham Retreat with Hot Tub! offers accommodations in Windham, 30 miles from Hudson Athens Lighthouse and 10 miles from Hunter Mount...
  • Parking
  • Spa and wellness centre

no reviews

from $386.43 Show details »

Holly Lodge - Ski Windham Hunter Catskills in Prattsville, USA

Holly Lodge - Ski Windham Hunter Catskil...

Holiday home in Prattsville near Windham, Florida , 12112 New York 23
Featuring a garden, Holly Lodge - Ski Windham Hunter Catskills features accommodations in Prattsville.
  • Pets allowed
  • Family rooms

Exceptional 2 Reviews 9.5

from $334.18 Show details »

Mountain Cabin with Scenic Views and Hot Tub in Windham, USA

Mountain Cabin with Scenic Views and Hot...

Holiday home in Windham, Florida , 15 Church Street
Mountain Cabin with Scenic Views and Hot Tub offers accommodations in Windham, 29 miles from Hudson Athens Lighthouse and 11 miles from Hunter Mountai...
  • Pets allowed

no reviews

from $258.06 Show details »

2 Mi to Windham Mountain Scenic Home with Fire Pit! in Windham, USA

2 Mi to Windham Mountain Scenic Home wit...

Holiday home in Windham, Florida
2 Mi to Windham Mountain Scenic Home with Fire Pit! offers accommodations in Windham, 10 miles from Hunter Mountain.
  • Parking
  • Pets allowed

no reviews

from $270.29 Show details »

Number of Holiday homes in Windham 39
Number of guest ratings 1,138
Average price per night $306.00
Lowest price per night $51,00
Highest price per night $1.339,96

Top 10 Cheapest Holiday-homes in Windham

Discover the Cheapest Holiday-homes in Windham – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Windham

Check out the Most Booked Holiday-homes in Windham – Based on Guest Popularity.

Holiday homes in Windham (Florida), comfortable and familiar

Staying in a holiday or vacation home in Windham can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Windham for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Windham should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com