Cottage vacation rentals in Windham

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Quick stats about cottage rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at R 3,432 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 80 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windham rentals

  • 4.9 Average rating

    Windham stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated cottage rentals in Windham

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite
The exterior of Cupcake Cottage is framed by lush greenery, featuring a well-maintained lawn and vibrant flower beds. A spacious deck extends from the house, inviting relaxation and enjoying the surrounding natural beauty. Sunlight filters through the leaves, highlighting the cottage's warm wooden facade.
Cottage in Roxbury
4.99 out of 5 average rating, 296 reviews

Cupcake Cottage! 1838 renovated barn, with views.

Spring has arrived! The flowers are popping up. Two night rentals are available from January-May. New 2026: Kitchen Aid Stand Mixer. Cupcake Cottage has had a total renovation: the same light, charm, and views remain but inside there is a new kitchen, flooring, and heating system. And outside, a new deck and porch configuration, windows, siding, roof and dormers. The house is an 1838 barn with old beams and rafters, and modern finishes of hemlock, red oak, and western red cedar throughout.

Guest favorite
An open-plan kitchen and dining area features a large wooden table surrounded by several chairs. A modern kitchen with dark cabinetry and stainless steel appliances is seen in the background. A wood stove is positioned near the window, which offers views of the snowy outdoor scenery.
Cottage in Saugerties
4.94 out of 5 average rating, 364 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

Top guest favorite
Cottage in Germantown
4.97 out of 5 average rating, 197 reviews

Loblolly Cottage

Loblolly Cottage is a peaceful retreat set among towering pines in the Hamlet of Germantown NY. A short stroll leads you to the heart of town where you will find an array of shops and restaurants, including the famed Otto's Market. Just minutes away you'll discover towns like Hudson, Rhinebeck, Tivoli, and Catskill that offer galleries, hiking trails, historic homes and landmarks and river views. Loblolly Cottage is one of the best one-of-a-kind vacation experiences in the Hudson Valley.

Top guest favorite
A stone patio is surrounded by vibrant flowers and greenery, featuring a wooden table with four chairs. The cottage's large window provides a view of the inviting outdoor space, where additional potted plants add a touch of color and natural beauty.
Cottage in Chichester
4.99 out of 5 average rating, 631 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek.

Guest favorite
A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.
Cottage in Rhinebeck
4.93 out of 5 average rating, 349 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

Guest favorite
A charming cottage is nestled among lush trees, featuring a brick chimney and light blue shutters. Steps lead up to a welcoming entryway, while the surrounding landscape showcases a gently sloping yard and greenery, adding to the peaceful ambiance.
Cottage in Prattsville
4.87 out of 5 average rating, 104 reviews

Pet friendly Cottage close to ski resorts

Pet friendly 2 bedroom cottage in the Catskills Mountain area. Kitchen, with updated appliances mid 2023, is equipped with an electric stove and new refrigerator. Gas grill on deck as well. Living room has a fireplace, TV, Wi-Fi, and a small dining area capable of seating 4 people. Outside has a large backyard with a lawn chairs, hammock and fire pit. Bathroom essentials are provided. Guest must bring wood for indoor fireplace. Check in and out times are flexible.

Top guest favorite
Cottage in Red Hook
4.98 out of 5 average rating, 730 reviews

bright serene + spacious barn @barn and bike

a bright serene space built by us on the property we live on. we are in - what we think - is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes all around. 6 quaint towns are within 10-25 minutes drive. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking (no cats) • we look forward to having you here!

Top guest favorite
Cottage in Halcott Center
4.98 out of 5 average rating, 365 reviews

Cozy Cottage with Stunning Mountain Views

Welcome to Halcott Cottage! Featuring gorgeous mountain views, less than two and a half hours from NYC, and ten minutes from Belleayre Ski Center, this cozy and private cottage is perfect for a romantic couples retreat, two couples, a small family, or a group of friends looking for a relaxing and quiet escape in the historic Catskills. The cottage is a short drive to Phoenicia, Woodstock, Andes, and Margaretville for shopping, dining, antiquing, skiing and exploring.

Guest favorite
A serene view of the cottage perched on a hillside is captured across the reflective waters of the creek. Lush greenery surrounds the area, with trees providing shade and the deck offering an inviting space for relaxation.
Cottage in Bloomington
4.97 out of 5 average rating, 576 reviews

'The Blue Jay Cottage' - Privacy With A View!

Come, get away from the craziness of life, calm your body, clear your mind and channel your energy by staying at a very special little gem. Once you arrive you won't want to leave. A newly renovated cozy cottage, where you won't believe your view when you wake up in the morning with your first cup of tea or coffee overlooking the best spot in this area from the deck. A perfect getaway on almost 5 acres of creek frontage to find your inner peace.

Top guest favorite
A rustic cottage is surrounded by lush greenery, featuring a wrap-around deck illuminated by string lights. The wooden structure is complemented by various plants and shrubs, offering a serene and inviting atmosphere. The entry is adorned with a partially covered porch, enhancing the cottage's natural charm.
Cottage in Phoenicia
4.94 out of 5 average rating, 302 reviews

Charming creekside cottage in Phoenicia

Come relax in one of the prettiest places in the Catskills. Enjoy views of the Stony Clove, while sipping coffee on the wrap-around deck. The location is private and quiet, yet convenient to all the region's many attractions - hiking, skiing, antiquing, eating. When you are done exploring, enjoy a dip in one of the largest, deepest swimming holes in the area. Perfect for small families and couples. License Number: 2022-STR-AO-081

Superhost
An open living space features vibrant green walls and large windows that invite natural light. A comfortable couch and a wooden coffee table are positioned on polished hardwood flooring. In the back, a dining area with a wooden bar and chairs is visible, offering views of the surrounding greenery.
Cottage in Catskill
4.93 out of 5 average rating, 150 reviews

Evergreen Escape - Woodsy Artistic Retreat

Floor to ceiling murals thoughtfully painted by a local artist cover every wall to seamlessly blend the interior living pace and outdoor Zen. Relax on the covered front porch or the private back deck with a fire pit situated directly next to hundreds of acres of forest. Stroll through the trees and explore the nearby woods or relax inside with all the comforts you'd expect of a newly renovated home.

Top guest favorite
Cottage in Chichester
4.93 out of 5 average rating, 122 reviews

Peaceful Cottage With Mountain Views

Forget your worries in this tranquil cottage, located on Catskill Mountains. This furnished 2-bedroom home is the ideal place for those who have an appreciation of solitude and nature. The cottage sits on 1 acre of land, with a wooden patio overlooking the mountain - just the perfect place for meditating over afternoon tea.

Popular amenities for Windham cottage rentals

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