Title: Windham Vacation Rentals from $285: Search Short-Term Rentals | Expedia.com

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6150553&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6150553&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=6150553&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=6150553&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windham vacation rentals

![Exterior](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/05713f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Kettle Brook Two Bedroom 1 Bath Ski In/Out | Living room | 47-inch LCD TV with cable channels, TV](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/12d879f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Bedrooms, Mountainside (Kettle Brook) | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/5237275c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/66b853e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Okemo Mountain Lodging by Vail Resorts

[](https://www.expedia.com/Ludlow-Hotels-Okemo-Mountain-Lodging.h32341945.Hotel-Information)

Clock Tower Base Area

7.8/10

Good

(28 reviews)

"I had an amazing time with my family, I will definitely be coming back "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Yenifer

$1,689 nightly

$1,908 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Okemo-Mountain-Lodging.h32341945.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/c93e763c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/fad6cb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/f8f558ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/66b559f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Hub! Family Home in West Dover

[](https://www.expedia.com/West-Dover-Hotels-Ski.h124177563.Hotel-Information)

West Dover

$474 nightly

$522 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/West-Dover-Hotels-Ski.h124177563.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/4994716e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snow and ski sports](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/1e2b3992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/a16eeef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/b907a89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Long Trail House at Stratton Mountain Resort

[](https://www.expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

Stratton

8.6/10

Excellent

(83 reviews)

"Nice place and great location!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

William

$361 nightly

$408 total

Apr 14 - Apr 15

Total with taxes and fees

[](https://www.expedia.com/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information)

![House (5 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/fc371b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/09450a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/7212c2d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (5 Bedrooms) | Interior](https://images.trvl-media.com/lodging/127000000/126490000/126481900/126481809/9b4bc035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

[](https://www.expedia.com/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.Hotel-Information)

Ludlow

$1,435 nightly

$1,578 total

May 1 - May 2

Total with taxes and fees

[](https://www.expedia.com/Ludlow-Hotels-Luxe-Mountain-Home-W-Chefs-Kitchen-Okemo-Views.h126481809.Hotel-Information)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/14ace880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/2220bc31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/0780f54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/121000000/120620000/120618700/120618609/b15a729a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

[](https://www.expedia.com/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

Newfane

$528 nightly

$575 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Newfane-Hotels-Outdoor-Adventure-Haven-14-Mi-To-Mount-Snow-Skiing.h120618609.Hotel-Information)

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.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-15&endDate=2026-04-16&regionId=6150553&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CONDO)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=COTTAGE)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CABIN)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Windham%2C+Vermont%2C+United+States+of+America&regionId=6150553&latLong=43.173435%2C-72.72345&adults=2&startDate=2026-06-30&d1=2026-06-30&endDate=2026-07-03&d2=2026-07-03&lodging=CHALET)

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## Top Windham Hotel Reviews

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg)

### The Manchester View

10/10 Excellent

"The "

[](https://expedia.com/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c_y.jpg)

### The Putney Inn

10/10 Excellent

"I stayed just for a night and it was the best hotel sleep I’ve had in ages. Check in was easy, staff were lovely, and parking was plentiful. "

[](https://expedia.com/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information)

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg)

### Pointe at Castle Hill Resort

8/10 Good

"Have stayed here many times. Close to town and Okemo. Very convenient."

[](https://expedia.com/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information)

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg)

### Colonial Motel And Spa

4/10 Poor

"Plenty of parking Clean - no bugs Goes downhill from there. Front desk people were polite but far from friendly. Major renovations need to be done before I will come back. Windows did not lock, which my husband discovered as we were getting ready for bed. He decided that they were too small for anyone to crawl through, but not a comforting feeling. Pool - closes at 5pm on Sunday - we arrived at 5:10 😳 Hot tub - closed for cleaning on Monday until 1pm, but check out is at 11am So I have no idea what the condition is of either, but I cannot imagine that they are in great shape. I should have known that 2 pools and a hot tub for that price was too good to be true "

[](https://expedia.com/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information)

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/fddf0cb9_y.jpg)

### The Equinox Golf Resort & Spa

10/10 Excellent

"We love the Equinox. We usually stay here during ski season. Always looking forward to rest after a long day of ski. Amenities are amazing, the restaurant and bar are great to eat and hangout. "

[](https://expedia.com/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information)

![Aspen At Manchester](https://images.trvl-media.com/lodging/11000000/10260000/10254500/10254459/cbf700aa_y.jpg)

### Aspen At Manchester

10/10 Excellent

"Clean room. Shops nearby"

[](https://expedia.com/Bennington-Hotels-Aspen-At-Manchester.h10254459.Hotel-Information)

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg)

### Hampton Inn Brattleboro

10/10 Excellent

"Nice"

[](https://expedia.com/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information)

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg)

### The Covered Bridge Inn

4/10 Poor

"The rrooms were clean, shower was great. Hallways dark, parking lot not to much lighting. There is no breakfast just coffee."

[](https://expedia.com/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information)

![Best Western Springfield Hotel](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae_y.jpg)

### Best Western Springfield Hotel

10/10 Excellent

"All good"

[](https://expedia.com/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information)

## Find out more about Windham

**Everything you need to know about Windham vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Windham vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $285 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Windham rentals**

At Expedia, we put the best Windham vacation 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 vacation.

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.

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- [Vacation Homes in Windham ](https://expedia.com/Windham-Private-Vacation-Homes.d6150553-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Condo Rentals in Windham ](https://expedia.com/Windham-Condos.d6150553-aaCondos.Travel-Guide-Accommodation)
- [Cottages in Windham ](https://expedia.com/Windham-Cottages.d6150553-aaCottages.Travel-Guide-Accommodation)
- [Cabin Rentals in Windham ](https://expedia.com/Windham-Cabins.d6150553-aaCabins.Travel-Guide-Accommodation)
- [Apartments in Windham ](https://expedia.com/Windham-Apartments.d6150553-aaApartments.Travel-Guide-Accommodation)
- [Chalets in Windham ](https://expedia.com/Windham-Chalets.d6150553-aaChalets.Travel-Guide-Accommodation)
- [B&B in Windham ](https://expedia.com/Windham-Bed-And-Breakfast.d6150553-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Farmstay in Windham ](https://expedia.com/Windham-Agritourism.d6150553-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Windham ](https://expedia.com/Windham-Motels.d6150553-aaMotels.Travel-Guide-Accommodation)
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- [Lodges in Windham ](https://expedia.com/Windham-Lodges.d6150553-aaLodges.Travel-Guide-Accommodation)
- [Aparthotels in Windham ](https://expedia.com/Windham-Apart-Hotels.d6150553-aaApartHotels.Travel-Guide-Accommodation)
- [Guest Houses in Windham ](https://expedia.com/Windham-Guest-Houses.d6150553-aaGuestHouses.Travel-Guide-Accommodation)
- [Inns in Windham ](https://expedia.com/Windham-Inns.d6150553-aaInns.Travel-Guide-Accommodation)
- [RV Parks in Windham ](https://expedia.com/Windham-RV-Parks.d6150553-aaRVParks.Travel-Guide-Accommodation)

## Frequently asked questions

### Are there vacation rentals in Windham?

### What's the top vacation rental that Windham has to offer?

### How many vacation rentals are there in Windham?

### What’s there to see and do in Windham?

### What’s a vacation rental in Windham like?

### Expedia's Latest Trends

Hotels

- [Top Hotels in Panton](https://expedia.com/Panton-Hotels.d3000473565.Travel-Guide-Hotels)
- [Brookline 4 Star Hotels](https://expedia.com/4Star-Brookline-Hotels.s40-0-d3000459594.Travel-Guide-Filter-Hotels)
- [Top Hotels in Westmore](https://expedia.com/Westmore-Hotels.d184081.Travel-Guide-Hotels)
- [Middlesex 5 Star Hotels](https://expedia.com/5Star-Middlesex-Hotels.s50-0-d3000391797.Travel-Guide-Filter-Hotels)
- [Wheelock 4 Star Hotels](https://expedia.com/4Star-Wheelock-Hotels.s40-0-d553248634998838654.Travel-Guide-Filter-Hotels)
- [Top Hotels in Mendon](https://expedia.com/Mendon-Hotels.d181428.Travel-Guide-Hotels)
- [Top Hotels in Jay](https://expedia.com/Jay-Hotels.d184053.Travel-Guide-Hotels)
- [Top Hotels in Island Pond](https://expedia.com/Island-Pond-Hotels.d184051.Travel-Guide-Hotels)
- [Top Hotels in Marlboro](https://expedia.com/Marlboro-Hotels.d6056722.Travel-Guide-Hotels)
- [Hartford Pet-friendly Hotels](https://expedia.com/Hartford-Hotels-Pet-Friendly-Hotel.0-0-d3000459649-tPetfriendlyHotel.Travel-Guide-Filter-Hotels)
- [Top Hotels in Lyndon](https://expedia.com/Lyndon-Hotels.d553248634999097886.Travel-Guide-Hotels)
- [Top Hotels in Berlin Corners](https://expedia.com/Berlin-Corners-Hotels.d6025629.Travel-Guide-Hotels)
- [Top Hotels in Hartford](https://expedia.com/Hartford-Hotels.d3000459649.Travel-Guide-Hotels)
- [West Haven 2 Star Hotels](https://expedia.com/2Star-West-Haven-Hotels.s20-0-d553248635975871796.Travel-Guide-Filter-Hotels)
- [Top Hotels in Bolton Valley](https://expedia.com/Bolton-Valley-Hotels.d56075.Travel-Guide-Hotels)

Flights

- [Middlesex Cheap Flights](https://expedia.com/lp/flights/3000391797/flights-from-middlesex)
- [Flights to BTV](https://expedia.com/Cheap-Flights-To-Berlin-Corners.d6025629.Travel-Guide-Flights)
- [Flights to VSF](https://expedia.com/Cheap-Flights-To-Ascutney.d6046953.Travel-Guide-Flights)
- [Wilder Cheap Flights](https://expedia.com/lp/flights/174820/flights-from-wilder)

Cars

- [Car rentals in Proctorsville](https://expedia.com/Car-Rentals-In-Proctorsville.d6023678.Car-Rental-Guide)
- [Car rentals in Wilder](https://expedia.com/Car-Rentals-In-Wilder.d174820.Car-Rental-Guide)
- [Car rentals in Hartford](https://expedia.com/Car-Rentals-In-Hartford.d3000459649.Car-Rental-Guide)
- [Car rentals in Graniteville-East Barre](https://expedia.com/Car-Rentals-In-Graniteville-East-Barre.d553248634998991025.Car-Rental-Guide)
- [Car rentals in Bolton Valley](https://expedia.com/Car-Rentals-In-Bolton-Valley.d56075.Car-Rental-Guide)

Vacation Rentals

- [Greensboro Bend Short Term Rentals](https://expedia.com/Greensboro-Bend-Vacation-Rentals.d3000459644.Travel-Guide-VacationRentals)
- [Westmore Short Term Rentals](https://expedia.com/Westmore-Vacation-Rentals.d184081.Travel-Guide-VacationRentals)
- [Jay Short Term Rentals](https://expedia.com/Jay-Vacation-Rentals.d184053.Travel-Guide-VacationRentals)

General

- [Visit Andover](https://expedia.com/Andover.dx6023580)
- [Visit Sudbury](https://expedia.com/Sudbury.dx3000381073)
- [Visit Hartford](https://expedia.com/Hartford.dx3000459649)

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