
Windham Vacations from $775
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Windham vacation packages
Price found within the past 48 hours. Click for updated prices.

The Mountain Inn at Killington
Price was $918, price is now $775 per person
$775
per person
May 5 - May 11
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
Love staying here. Staff is amazing! Super attentive. Great food at the restaurant. Cozy lodge feel. Basically on the mountain Without being ski in ski out. This is where I always stay when visiting killington.
Reviewed on Mar 11, 2026

The Quechee Inn at Marshland Farm
Price was $988, price is now $827 per person
$827
per person
May 5 - May 11
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9/10 Wonderful! (1,001 reviews)
Lovely historic property. Great location for skiing
Reviewed on Mar 4, 2026


Emrose Luxury Cabins
Price was $1,017, price is now $901 per person
$901
per person
May 5 - May 11
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9/10 Wonderful! (81 reviews)
We had such an amazing stay at these cabins—truly the perfect start to an unforgettable weekend. We were in town for a ski trip, and with our friend planning to propose, this cabin was the ideal setting to set the mood the night before. The atmosphere was cozy, romantic, and exactly what we hoped for.
Each cabin has its own special feel and unique architecture, which made the experience even more memorable and charming. The cabins are conveniently located, and we loved that there are hot tubs spread throughout the property. The hosts were incredibly responsive and helpful from start to finish, especially with food recommendations. When we let them know we were on our way, they even had the hot tub heating up and ready for us upon arrival, which was such a thoughtful touch.
I also reached out ahead of time to ask if two cabins next to each other could be accommodated, and they were beyond helpful and made the process so easy. You can really tell they care about their guests’ experience.
Helpful tips for future guests: bring slippers to wear inside the cabins since no shoes are allowed, and definitely bring a robe for the walk to the hot tub—it makes the experience even better!
We couldn’t have asked for a better stay and would absolutely recommend these cabins to anyone looking for a relaxing, memorable getaway. ⭐️⭐️⭐️⭐️⭐️
Reviewed on Feb 20, 2026

Castle Hill Resort And Spa
Price was $1,202, price is now $1,065 per person
$1,065
per person
May 5 - May 11
just found
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9/10 Wonderful! (108 reviews)
We used to spend a good deal of time in ludlow . Recently my wife and I have been visiting about once per year. Back in the day we very much enjoyed the castle inn for its great food. We thoghtvwe would stay for a couple of nights.
We hoped to ski one day. We went into the inn with a big ski bag and they wanted us to climb 3 levels with it. Luckily there was a person who became available to help. The room was a large king. The furnishings were represetative of a classic inn.
Very old but not broken or too worn. However the heat was set so high it was unconfortable with no mechanism to lower
it. .it was very difficult to sleep . We also learned that they dont do dinners on sundays. So we changed some long standing plans. Upon asking if they had a shuttle to ski area we were told we needed to walk to the. hotel next door. Something untenable in ski boots. When we got back went to their gym. It was nice. But locker rooms were somewhat unkept and aged out
Most disappointing was after our return to the room on day two the room was not cleaned. Upon reaching out they said there was no cleaning services for overnight guests. But if we needed towels they would bring it up. Given there was no dinner we found a place closer to the highway and decided to just headed home. We wanted to love the inn. But from our viewpoint if they want to remain the wonderful experience we expected they need to reconsider there amenities for folks looking for a memorable few days
Reviewed on Mar 10, 2026
Windham Hotel Deals

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
Windham VT
10/10 Exceptional! (57 reviews)
We had the best time at this beautiful house. Very clean and perfect for a large group
Reviewed on Feb 22, 2026

Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$135 nightly
The price is $146 total per night from Mar 16 to Mar 17
$146 total
Mar 16 - Mar 17
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Yes
Reviewed on Mar 11, 2026

Hideaway Inn Mt. Snow
270 Handle Rd West Dover VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Mar 23 to Mar 24
$149 total
Mar 23 - Mar 24
Total with taxes and fees
8.8/10 Excellent! (70 reviews)
Great location. Clunky check-in as all virtual. Hot tub, which is the reason booked was broken, saunas did not heat up, could not adjust the heat in the room, so even though we tried to turn it off it was 80’ overnight. Machine for tea also didn’t work. Clean rooms but the hot tub and heat issues ...
Reviewed on Mar 10, 2026
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.
Find the Best Windham Vacation Packages
Windham Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Magic Mountain Ski Resort
- Hotels near Lowell Lake State Park
- Hotels near Ball Mountain State Park
- Hotels near Ball Mountain Dam
- Hotels near Jamaica State Park
- Hotels near Viking Nordic Center
- Hotels near Stratton Mountain Golf Course
- Hotels near Plummer's Sugar House
- Londonderry Hotels
- Hotels near Grafton Ponds Outdoor Center
- Cabin Rentals in Londonderry
- Resorts & Hotels with Spas in Londonderry
- Hotels with Restaurants in Londonderry
- Pet-Friendly Hotels in Londonderry
- Ski Hotels in Londonderry
- Motels in Londonderry
- Cottages in Londonderry
- Hotels with a Pool in Londonderry
- Cheap Hotels in Londonderry
- Condo Rentals in Londonderry
- Hotels with Fireplaces in Londonderry
- Luxury Hotels in Londonderry
- Hotels with an Outdoor Pool in Londonderry
- 5 Star Hotels in Londonderry
- Extended Stay Hotels in Londonderry
- B&B in Londonderry
- Family Hotels in Londonderry
- Romantic Hotels in Londonderry
- 4 Star Hotels in Londonderry
- Hotels with Hot Tubs in Londonderry
- Hotels with Air Conditioning in Londonderry
- Rv Parks in Londonderry
- Golf Hotels in Londonderry
- Hotels near West River
- Hotels near The Nature Museum
- Hotels near Gallery North Star
- Jamaica Hotels
- Hotels near Hunter Gallery of Fine Art
- Cabin Rentals in Jamaica
- Pet-Friendly Hotels in Jamaica
- Resorts & Hotels with Spas in Jamaica
- Ski Hotels in Jamaica
- Family Hotels in Jamaica
- Romantic Hotels in Jamaica
- Motels in Jamaica
- Hotels with Fireplaces in Jamaica
- Rv Parks in Jamaica
- 5 Star Hotels in Jamaica
- 3 Star Hotels in Jamaica
- B&B in Jamaica
- Hotels with a Pool in Jamaica
- Vacation Homes in Jamaica
- Hotels & Resorts for Couples in Jamaica
- Lodges in Jamaica
- Apartments in Jamaica
- Non-Smoking Hotels in Jamaica
- Golf Hotels in Jamaica
- Hotels with a Gym in Jamaica
- Farmstay in Jamaica
- Historic Hotels in Jamaica
- Hotel with a Concierge Hotels in Jamaica
- Magic Mountain Ski Resort
- Lowell Lake State Park
- Ball Mountain Dam
- Jamaica State Park
- Stratton Tennis School
- Viking Nordic Center
- Plummer's Sugar House
- Grafton Ponds Outdoor Center
- West River Farmers Market
- The Nature Museum
- Gallery North Star
- Vermont Museum of Mining and Minerals
- Grafton Vacations
- Visit Londonderry
- Hot Glass Works
- Visit Jamaica
- Car rentals near Viking Nordic Center
- Car rentals near Londonderry
- Car rentals near Jud Hartmann Gallery
- Avis Rental Cars in Jamaica
- Car rentals near Jamaica
- United Rental Cars in Jamaica
- National Car Rental Rental Cars in Jamaica
- Thrifty Car Rental Rental Cars in Jamaica
- Sixt Rental Cars in Jamaica
- Apex Car Rentals Rental Cars in Jamaica
- Advantage Rent-A-Car Rental Cars in Jamaica
- Essence Car Rental Rental Cars in Jamaica
- Enterprise Rental Cars in Jamaica
- Drive-A-Matic Rental Cars in Jamaica
- Budget Canaries Rental Cars in Jamaica
- Payless Rental Cars in Jamaica
- Mex Rent A Car Rental Cars in Jamaica
- Pickup Car Rentals in Jamaica
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















