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Southern Vermont Vacation Packages

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Southern Vermont Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $634, price is now $543 per person
$543
per person
Dec 17 - Dec 21
found 13 hours ago
Roundtrip flight included
Orlando (MCO) 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.

The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,495, price is now $1,096 per person
$1,096
per person
Jan 16 - Jan 19
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Stay at this hotel in Cornwallville. Enjoy free WiFi, free parking, and a garden. Popular attractions Elm Ridge Wild Forest and Zoom Flume are located nearby.

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,087, price is now $838 per person
$838
per person
Dec 17 - Dec 21
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Keets Brook Road Conservation Area are located nearby.

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,766, price is now $1,381 per person
$1,381
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.

Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Price was $799, price is now $644 per person
$644
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Book a stay at this business-friendly hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Birch Body Care and Volunteer Fireman's Hall and Museum of Kingston are located nearby.
Excellent stay. Clean, great location. Large rooms

Reviewed on Oct 28, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,814, price is now $1,467 per person
$1,467
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.

The Old Catskill Game Farm Inn

The Old Catskill Game Farm Inn

3.5 out of 5
Price was $3,242, price is now $2,632 per person
$2,632
per person
Jan 16 - Jan 19
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Book a stay at this historic guesthouse in Catskill. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Kaaterskill Falls and North-South Lake Campground & Day Use Area are located nearby.
Everything was amazing. Shawn was awesome. He greeted you when we came in. It's definitely experiences. All I can say we had a great time. A little quirky.Amazing history set on 200 acres closed down zoo

Reviewed on Sep 21, 2026

The Painted Lady by Avantstay Grand Victorian + Balcony Firepit + BBQ

The Painted Lady by Avantstay Grand Victorian + Balcony Firepit + BBQ

3 out of 5
Price was $1,566, price is now $1,335 per person
$1,335
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Stay at this cottage in Catskill. Enjoy free parking, balconies, and in-room washers/dryers. Popular attractions Thomas Cole National Historic Site and Avalon Lounge are located nearby.

Southern Vermont Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $799, price is now $644 per person
$644
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Save 100% on your flight
Price was $1,265, price is now $805 per person
$805
per person
Dec 17 - Dec 21
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $1,495, price is now $1,096 per person
$1,096
per person
Jan 16 - Jan 19
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,087, price is now $838 per person
$838
per person
Dec 17 - Dec 21
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)

Southern Vermont Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,549, price is now $1,333 per person
$1,333
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,766, price is now $1,381 per person
$1,381
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,814, price is now $1,467 per person
$1,467
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Clock Tower Base Area
Price was $3,002, price is now $2,577 per person
$2,577
per person
Dec 16 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)

Top Flight Deals

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

American Airlines
Tue, Nov 17 - Sat, Nov 21
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sat, Nov 21, priced at $167 found 3 hours ago
Allegiant Air
Fri, Jan 15 - Sun, Jan 17
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$213 Roundtrip, found 10 hours ago
$213
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Fri, Jan 15 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Jan 17, priced at $213 found 10 hours ago
Southwest Airlines
Wed, Dec 9 - Wed, Dec 16
TPA
Tampa Intl.
ALB
Albany Intl.
$271 Roundtrip, found 16 hours ago
$271
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Wed, Dec 9 from Tampa Intl. to Albany Intl., returning Wed, Dec 16, priced at $271 found 16 hours ago
Bargain Flight
Sat, Dec 5 - Tue, Dec 8
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$312 Roundtrip, found 6 hours ago
$312
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Sat, Dec 5 from Sky Harbor Intl. to Albany Intl., returning Tue, Dec 8, priced at $312 found 6 hours ago