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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Colonial Motel

Colonial Motel

3 out of 5
Price was $702, price is now $682 per person
$682
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Springfield (VSF)
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
The room was dirty and smelled musty and of urine. The hallways have all broken down ice machines and the breakfast was non-existent.

Reviewed on Sep 6, 2026

1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $877, price is now $823 per person
$823
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $790, price is now $751 per person
$751
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $954, price is now $912 per person
$912
per person
Oct 26 - Oct 29
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
Had an amazing time here, everyone was so friendly and welcoming and the property itself was beautiful! Breakfast was delicious and we were a huge fan of the late night snacks too! We’re looking forward to staying again the next time we visit the area!

Reviewed on Aug 27, 2026

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $756, price is now $729 per person
$729
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Accesible to shopping and road. Not safe for families and bring your own cleaning supplies and linens.

Reviewed on Sep 9, 2026

Black Mountain Inn

Black Mountain Inn

2 out of 5
Price was $744, price is now $719 per person
$719
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and United States Navy Seabee Bridge are located nearby.
It was a very good experience overall for a one night stay. Clean room, comfortable bed, quiet surroundings. Staff very helpful!

Reviewed on Sep 10, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $798, price is now $771 per person
$771
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $803, price is now $803 per person
$803
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
The room was very clean, the tv was very nice (my husband is now looking for one like it), it was quiet, which surprised me because it's near a busy highway. Breakfast was really good & a great variety! Only thing that could be improved is the mattress on the bed - it was a bit flat, but was comfortable enough.

Reviewed on Sep 7, 2026

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $954, price is now $912 per person
$912
per person
Oct 26 - Oct 29
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Springfield (VSF)