Search Deals on
Woodstock Vacation Packages

Build your package with 2 more options

Woodstock Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $632, price is now $516 per person
$516
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $5,226, price is now $3,994 per person
$3,994
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Book a stay at this spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $771, price is now $597 per person
$597
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was $828, price is now $688 per person
$688
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
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. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,490, price is now $1,244 per person
$1,244
per person
Jan 30 - Feb 3
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
The One Cat B&B

The One Cat B&B

2.5 out of 5
Price was $708, price is now $599 per person
$599
per person
Jan 30 - Feb 3
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this B&B in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions New England Youth Theatre and Brattleboro Museum & Art Center are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,075, price is now $921 per person
$921
per person
Feb 10 - Feb 15
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $784, price is now $676 per person
$676
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
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 helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.

Woodstock Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The One Cat B&B

The One Cat B&B

2.5 out of 5
Price was $708, price is now $599 per person
$599
per person
Jan 30 - Feb 3
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,490, price is now $1,244 per person
$1,244
per person
Jan 30 - Feb 3
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,117, price is now $976 per person
$976
per person
Feb 11 - Feb 15
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $2,761, price is now $2,427 per person
$2,427
per person
Feb 11 - Feb 15
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)

Woodstock Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $632, price is now $516 per person
$516
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $5,226, price is now $3,994 per person
$3,994
per person
Feb 12 - Feb 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $771, price is now $597 per person
$597
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was $828, price is now $688 per person
$688
per person
Feb 4 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Tue, Feb 3 - Sat, Feb 7
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$270 Roundtrip, found 13 hours ago
$270
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Tue, Feb 3 from John F. Kennedy Intl. to Lebanon Municipal, returning Sat, Feb 7, priced at $270 found 13 hours ago
JetBlue Airways
Wed, Feb 4 - Sat, Feb 7
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$273 Roundtrip, found 13 hours ago
$273
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Wed, Feb 4 from John F. Kennedy Intl. to Lebanon Municipal, returning Sat, Feb 7, priced at $273 found 13 hours ago
American Airlines
Mon, Feb 9 - Mon, Feb 9
LGA
LaGuardia
LEB
Lebanon Municipal
$291 Roundtrip, found 15 hours ago
$291
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Mon, Feb 9 from LaGuardia to Lebanon Municipal, returning Mon, Feb 9, priced at $291 found 15 hours ago
JetBlue Airways
Tue, Feb 3 - Sat, Feb 7
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$294 Roundtrip, found 13 hours ago
$294
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Tue, Feb 3 from John F. Kennedy Intl. to Lebanon Municipal, returning Sat, Feb 7, priced at $294 found 13 hours ago