Windham Holiday Rentals from AU$338: Search Short-Term Rentals

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Our top choices for Windham holiday rentals

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

includes taxes & fees

8 Sept - 9 Sept

2. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton

includes taxes & fees

8 Sept - 9 Sept

3. Long Trail House at Stratton Mountain Resort

Stratton

William

includes taxes & fees

7 Sept - 8 Sept

4. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

Stratton

includes taxes & fees

19 Sept - 20 Sept

5. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Stratton

eric m.

includes taxes & fees

8 Sept - 9 Sept

6. Cozy Bromley Retreat

Bromley Mountain

Janja L.

includes taxes & fees

6 Sept - 7 Sept

7. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Londonderry

Meghan R.

includes taxes & fees

9 Sept - 10 Sept

8. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Stratton Mountain

Jason S.

includes taxes & fees

7 Sept - 8 Sept

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Top Windham Hotel Reviews

Bromley View Inn

10/10 Excellent

"Exceptional stay. Many amenities here. Separate areas for pool table and community TV’s or games. Views were great. Breakfast was good and even had gluten free bread. 24/7 hot coffee and tea with Keurig. Front desk lady was wonderful- so helpful and kind. 10/10 stay."

Kimpton Taconic Hotel by IHG

8/10 Good

"My room had candy on side table and needed to have phone cleaned. Older property has character but needs attention in rooms. Don't pay for valet parking basically the same as self parking. Upon check out they handed me the keys to get car. I think it was overpriced for what you get. Manchester is a cute town. Nothing in the room to make coffee and had to buy water no refrigerators as well"

Hideaway Inn Mt. Snow

10/10 Excellent

"We will definitely return to the Hideaway! We got a text before arrival with our room number and code which was very convenient. The hotel is warm and cozy and beautifully decorated. There is neat stuff to look at everywhere. The 3 floors of common spaces were really cool with a lot to offer, like a water bottle filler and coffee maker. It could use to be cleaned a little more often. When we arrived, the playroom had toys all over the floor and there were sticky drink marks on the bar and crumbs on the coffee table. Someone had crushed the chalk under the dart board and all but 1 of the darts was broken. Regardless, we had a blast playing classic Mario on the arcade game. The living room upstairs was gorgeous, next time we will be sure to use that to play games and maybe watch a movie. We didn’t use the pool because it looked green (we opted to go to the lake instead) but we did make a fire and made s’mores down at one of the fire pits on our second night which was so nice to have. The closet in the hallway to grab towels and such is super convenient and the manager was only a text away if you needed anything. Our room was beautiful and so big. We loved the balcony and the record player in the room was a cool touch my boys had fun listening to. This is a very quiet property with a lot to keep families occupied or just relax and enjoy nature. We had a wonderful stay and when we met the manager she was so sweet! We absolutely loved it and will return for future VT trips."

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

10/10 Excellent

"We had the absolute best time at Suki’s property. Even better than the photos, the pool, house, seclusion, outdoor dining area, all of it was perfect for our golf trip and the best summer weekend. More beds than we could count, the home was clean and very comfortable. Highly recommend!"

Find out more about Windham

Everything you need to know about Windham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Windham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windham holiday rentals we have selected for you start as low as AU$338 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windham has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: This highly rated holiday home rental in Windham is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Windham stay.

What’s there to see and do in Windham?

Explore the area and family-friendly sights such as Vermont Country Store, or get out into nature at a spot like Lowell Lake State Park. In the wider area, you’ll find Magic Mountain Ski Resort and Jamaica State Park.

What’s a holiday rental in Windham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip.

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Check prices for these dates

Our top choices for Windham holiday rentals

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2. Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

3. Long Trail House at Stratton Mountain Resort

4. Walk to lifts, condo at Stratton Mountain, fireplace, pool, hot tubs, sauna

5. Lovely ski-in/out condo steps from ski lift with trails and amazing views

6. Cozy Bromley Retreat

7. Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

8. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

9. Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

10. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

11. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

12. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

13. The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

14. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

15. Charming Chester Farmhouse near Near VT Slopes

16. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

17. Long Trail House South Wing 2B2B Condo

18. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

19. The Vermont A-Frame Mountain Retreat

Find holiday rentals that suit your style

Top Windham Hotel Reviews

Bromley View Inn

The Manchester View

Kimpton Taconic Hotel by IHG

Comfort Inn & Suites Brattleboro I-91

Hampton Inn and Suites Manchester

The Putney Inn

Hideaway Inn Mt. Snow

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Find out more about Windham

Frequently asked questions

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