Windham Vacations
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Windham Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Black Bear Lodge at Stratton Mountain Resort
Price was $966, price is now $895 per person
$895
per person
Oct 1 - Oct 7
found 9 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rutland (RUT)
Book a stay at this ski resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stratton Mountain Resort and Villager Ski Lift are located nearby.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $1,401, price is now $1,217 per person
$1,217
per person
Oct 1 - Oct 7
found 9 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.
Very quiet location secluded and peaceful.
Location is not identified, no road sign or driveway entrance address. I booked within 3 days of check-in, instructions did not get emailed until after check in time, host did answer phone when called but email was received 30 minutes later.
It's a unique place, space is good, lots of amenities to cook and eat. Two bathrooms. Two showers. Lots of hot water and strong water pressure. Most of the unit is updated and modern. However it's tired, worn and dirty. The sofa was covered in dog hair, not just a little bit. It was all over our socks, clothing and floating around. The bathroom shower needed cleaning, walls needed wiping, carpet on stairs all stained and dirty. It you are used to hotels this will disappoint you.
Reviewed on May 10, 2026
The Mountain Inn at Killington
Price was $1,425, price is now $1,244 per person
$1,244
per person
Oct 1 - Oct 7
found 9 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
This property is liking being home. Everyone was very helpful and welcoming. I needed to call the desk twice for something and they were at my room with what I needed in minutes. The one thing I would let others know is it is an older building so no elevator. It was a bit of a struggle for this 68 year old to lug my bags up three flights of steps especially since I was exhausted from my seven hour drive to get here from Pennsylvania. E still very much enjoyed our stay and the morning continental breakfast and readily available free bottles of water.
Reviewed on Jul 23, 2026
North Star Lodge and Resort
Price was $1,393, price is now $1,238 per person
$1,238
per person
Oct 1 - Oct 7
found 9 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Absence de personnel au desk lors de notre départ à 7h le matin. Restaurant ouvert seulement les vendredis et samedis.
Reviewed on Jul 22, 2026
Long Trail House at Stratton Mountain Resort
Price was $1,667, price is now $1,526 per person
$1,526
per person
Oct 1 - Oct 7
found 9 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rutland (RUT)
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager Ski Lift are located nearby.
Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained
Reviewed on Jan 31, 2026
Vantage Point Villas at Stratton Mountain Resort
Price was $1,392, price is now $1,311 per person
$1,311
per person
Oct 1 - Oct 7
found 9 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rutland (RUT)
Book a stay at this ski hotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Tamarack Ski Lift are located nearby.
Beautiful, secluded little area up in the mountain. It was so nice that there was firewood and a wood burning fireplace inside the property.
Reviewed on Jun 26, 2026
Windham Vacation Packages
Trying to save some money and some time on your upcoming vacation to Windham? Well, AARP Travel Center Powered by Expedia® is here to help. We're here to book everything you'll need to make your Windham trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you. AARP Travel Center has an incredible selection of flights and hotels, as well as local endeavors to pull from.
Windham Hotel Deals
Our listings include lodgings that are close to all the Windham points of interest, and some that are just outside the city center for a peaceful retreat.
We have great deals on everything from luxury hotels that check off all the vacation must-haves to affordable accommodations perfect for those on wanting to save a little money. You can look through our vast catalog of options and choose the accommodation that is perfect for you. With AARP Travel Center's Windham hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.
Things to do in Windham
The fact that you are going to Windham means your holiday will already be off to a good start. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Book Together and Save
As an AARP Member, you get to cash in on all the great savings. You can save on select hotels worldwide, flights, and rental cars. No matter what Windham vacation package you pick, your membership savings helps you get a great deal. So what are you waiting for? Book now and get ready for your Windham vacation.
Top Hotel Deals
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
28.16 km from city center
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
Colonial Motel
889 Putney Rd Brattleboro VT
35.39 km from city center
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
26.92 km from city center
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
26.32 km from city center
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
27.48 km from city center
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
34.33 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Comfort Inn & Suites Brattleboro I-91
1186 Putney Road Brattleboro VT
34.66 km from city center
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
28.31 km from city center
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ...
Brittany Motel
1056 Main Street/Historic Route 7A Manchester Center VT
30.36 km from city center
Stay at this motel in Manchester Center. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
24.17 km from city center
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
25.16 km from city center
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
27.73 km from city center
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in ...
The Putney Inn
57 Putney Landing Rd Putney VT
28.58 km from city center
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.