Cheap Vacations in Windham County

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Windham County vacations

Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,399, price is now $1,125 per person
$1,125
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,260, price is now $1,917 per person
$1,917
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,585, price is now $1,412 per person
$1,412
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,512, price is now $1,361 per person
$1,361
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Summit Lodge

Summit Lodge

3 out of 5
Price was $1,647, price is now $1,559 per person
$1,559
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $1,437, price is now $1,363 per person
$1,363
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $1,586, price is now $1,513 per person
$1,513
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,403, price is now $1,348 per person
$1,348
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Killington Haus

Killington Haus

2 out of 5
Price was $1,260, price is now $1,220 per person
$1,220
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
The Waffelhaus In Killington 4 Bedroom Home

The Waffelhaus In Killington 4 Bedroom Home

3 out of 5
Price was $4,772, price is now $4,712 per person
$4,712
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)

4-night Windham County vacations

Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,399, price is now $1,125 per person
$1,125
per person
Oct 1 - Oct 5
found 15 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,260, price is now $1,917 per person
$1,917
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,585, price is now $1,412 per person
$1,412
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,512, price is now $1,361 per person
$1,361
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Summit Lodge

Summit Lodge

3 out of 5
Price was $1,647, price is now $1,559 per person
$1,559
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $1,437, price is now $1,363 per person
$1,363
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $1,586, price is now $1,513 per person
$1,513
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,403, price is now $1,348 per person
$1,348
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Killington Haus

Killington Haus

2 out of 5
Price was $1,260, price is now $1,220 per person
$1,220
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
The Waffelhaus In Killington 4 Bedroom Home

The Waffelhaus In Killington 4 Bedroom Home

3 out of 5
Price was $4,772, price is now $4,712 per person
$4,712
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Whitetail Chalet 4 Bedroom Home

Whitetail Chalet 4 Bedroom Home

3 out of 5
Price was $3,151, price is now $3,115 per person
$3,115
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)
Fall Line Condos by Killington VR - 3 Bedrooms

Fall Line Condos by Killington VR - 3 Bedrooms

3.5 out of 5
Price was $3,061, price is now $3,027 per person
$3,027
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Rutland (RUT)

Top places to visit in Windham County

A calm lake reflecting a forest with autumn foliage.
FlightsFlightsHotelsHotels

Brattleboro

Brattleboro

Flight deals to Windham County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Sep 28 - Sun, Oct 4
EWR
New York
RUT
Rutland
$503 Roundtrip, found 2 days ago
$503
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep 28 from New York to Rutland, returning Sun, Oct 4, priced at $503 found 2 days ago
Sun, Sep 20 - Sun, Sep 27
EWR
New York
RUT
Rutland
$513 Roundtrip, found 1 day ago
$513
Roundtrip
found 1 day ago
Select United flight, departing Sun, Sep 20 from New York to Rutland, returning Sun, Sep 27, priced at $513 found 1 day ago
Mon, Sep 28 - Sun, Oct 4
EWR
New York
RUT
Rutland
$518 Roundtrip, found 2 days ago
$518
Roundtrip
found 2 days ago
Select United flight, departing Mon, Sep 28 from New York to Rutland, returning Sun, Oct 4, priced at $518 found 2 days ago

Top rated hotels for your Windham County vacation

Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
10.52 mi from city center
$140 nightly
The price is $153 total per night
$153 total
Sep 2 - Sep 3
Total with taxes and fees
When you stay at Latchis Hotel in Brattleboro, you'll be near ski lifts, just steps from Latchis Theatre and 5 minutes by foot from The Stone Church.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Free Cancellation
12.05 mi from city center
$163 nightly
The price is $179 total per night
$179 total
Sep 30 - Oct 1
Total with taxes and fees
Located in West Dover, Grand Summit Resort, A Vail Resorts Property is a 1-minute drive from Mount Snow and 7 minutes from Mount Snow Golf Course.
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free Cancellation
Reserve now, pay when you stay
8.86 mi from city center
$84 nightly
The price is $93 total per night
$93 total
Sep 2 - Sep 3
Total with taxes and fees
A stay at Colonial Motel places you in the heart of Brattleboro, within a 5-minute drive of New England Center for Circus Arts and Brattleboro Common.
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.