Windham Vacation Rentals from AED 514: Search Short-Term Rentals

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Our top choices for Windham vacation rentals

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Windham

Michael C.

AED 817 total

includes taxes & fees

12 Aug - 13 Aug

2. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Windham

Ahmad O.

AED 575 total

includes taxes & fees

16 Aug - 17 Aug

3. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham

Cristina L.

AED 2,221 total

includes taxes & fees

12 Aug - 13 Aug

4. 'The Mountain House:' Windham Retreat w/ Hot Tub!

Windham

Teresa G.

AED 2,971 total

includes taxes & fees

23 Aug - 24 Aug

5. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

Windham

Melissa R.

AED 2,154 total

includes taxes & fees

18 Aug - 19 Aug

1 bedroom, in-room safe, WiFi (free), bed sheets

6. Iconic Glass Mirror Cabin ·Mountain View ·Private Fire Pit ·3 Min to Windham Mtn

Windham

AED 998 total

includes taxes & fees

8 Sep - 9 Sep

7. 'the Mountain House:' Windham Retreat w/ Hot Tub!

Windham

AED 2,903 total

includes taxes & fees

23 Aug - 24 Aug

8. Pines Vignette • Modern 3BR Home in Windham

Windham

William H.

AED 1,928 total

includes taxes & fees

8 Sep - 9 Sep

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Top Windham Hotel Reviews

Lake view Cabin on Lake Heloise

10/10 Excellent

"for my first stay using vrbo this cabin did not disappoint. everything was lovely, clean, and overall a great getaway! the host and the property made everything feel easy and comfortable! we will definetly be looking to stay again."

Hotel Vienna

10/10 Excellent

"Great weekend visit at Hotel Vienna with our 2 small dogs! Check in and check out were super easy, staff was helpful and accommodating, and the property was really quiet, very clean and super well maintained. The bathrooms were obviously recently renovated and very tastefully done, the bed was firm and linens soft and comfy. Breakfast was pastries, cereal, and yogurt; all were high quality, fresh and delicious. Cappuccino and tea were lovely. Shower pressure could have been a bit better, but that was literally the only downside. We did not have a chance to use the pool, but it looked very clean, located in a nice, stand-alone building with windows and skylights. Barrel sauna is just outside on the deck, and both are is surrounded by beautiful landscaping. The main building also has two sunny, well furnished decks, and there are fire pits with Adirondack chairs located about the property, and there's direct access to the Windham Path and dog park. Sad I missed the free Saturday morning yoga, but I'll definitely try to make it next time. All in all, this hotel was perfect, peaceful, and we'll definitely be back to explore all the things we missed!"

Wylder Hotel Windham

10/10 Excellent

"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations for fire pits and the staff will help you get a raging fire going immediately upon request. The golf course was simply beautiful and if that is your thing, absolutely a must. The restaurant on the grounds was terrific as was the bakery for breakfast and goodies. The buildings themselves are 150 years old and are lovely to check out just for that. I would certainly return in the future."

The Graham & Co.

10/10 Excellent

"This was my family’s third time staying at the Graham & Co. and every single stay has been wonderful. My family has grown a lot since our first stay 10 years ago, so staying in the bungalow gave everyone enough space while keeping us close. The room and grounds are very clean and well kept. The staff were so attentive. We arrived very late and they were great about giving us an option of seamless access to our room. We will certainly be back soon."

Frequently asked questions

Can I find vacation rentals in Windham?

Yes, we give you a choice of vacation rentals close to top points of interest in Windham, or you can select a more remote option if you'd like a relaxing place to stay. Discover why Windham is known for its ski slopes and mountain landscape. While you're here, grab a bite or have a drink at the coffeehouses.

What are some of the best vacation rentals in Windham?

Catskill Mountain Retreat -- private, beautiful views, hot tub, game rm, firepit: This vacation home rental outside of Windham is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a library, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Windham?

With 147 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What can I see and do in Windham?

Elm Ridge Wild Forest and Ashland Park are a couple of lovely local spots to get outside and enjoy nature. Windham Country Club and Windham Mountain Resort are other places to visit while you're in town.

What are vacation rentals like in Windham?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Windham. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.

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Our top choices for Windham vacation rentals

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

2. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

3. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

4. 'The Mountain House:' Windham Retreat w/ Hot Tub!

5. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

6. Iconic Glass Mirror Cabin ·Mountain View ·Private Fire Pit ·3 Min to Windham Mtn

7. 'the Mountain House:' Windham Retreat w/ Hot Tub!

8. Pines Vignette • Modern 3BR Home in Windham

9. Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway

10. Condo in Windham Mountain Village

11. Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

12. Beautiful Windham Chalet 2 minutes to Town and the Mountain

13. Spacious King Suite · Full Kitchen · Dining · Fireplace · Private Deck ·Sleeps 4

14. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

15. Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4

16. Presidential Duplex · Full Kitchen ·Wraparound Terrace ·Marble Jacuzzi ·Sleeps 4

17. Duplex King Suite · Marble Jacuzzi · Gas Fireplace · Steam Shower · Sleeps 4

18. King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4

19. 2BR/2BA Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 6

20. 2BR/2BA Suite + Loft · Full Kitchen · Fireplace · Private Deck · Sleeps 6+

Find vacation rentals that suit your style

Top Windham Hotel Reviews

Lake view Cabin on Lake Heloise

Eastwind Windham

Hotel Vienna

Wylder Hotel Windham

Jimmy OConnors Windham Mountain Inn

The Graham & Co.

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Emerson Resort & Spa

The Winwood Condominiums

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