Search Deals onPlainfield Vacation Packages
Plainfield Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Bentley House Bed and Breakfast
Price was $523, price is now $439 per person
$439
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
Clean, comfortable, convenient. We couldn't stay for breakfast.
Reviewed on Nov 8, 2026

Lincoln Inn & Gallery
Price was $1,266, price is now $718 per person
$718
per person
Dec 17 - Dec 21
just found
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
The hotel was amazing and the staff was so kind. Luke was working the front desk and made sure we had everything we needed. The hotel and property are beautiful. We really enjoyed our time and can't wait to come back!
Reviewed on Nov 8, 2026

Latchis Hotel
Price was $631, price is now $501 per person
$501
per person
Dec 17 - Dec 21
just found
Roundtrip non-stop 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.

Lake Bomoseen Lodge
Price was $743, price is now $591 per person
$591
per person
Dec 17 - Dec 21
just found
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
This property is fantastic. Definitely will stay again if I'm in the area. Check out the tap room. The food was delicious.
Reviewed on Nov 8, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $647, price is now $550 per person
$550
per person
Dec 17 - Dec 21
just found
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions T-Bar and Rope Tow are located nearby.
We were so happy with everything
Clean linens
Well stocked kitchen
Great grounds
Helpful staff
One minor issue--heat in halls too high, like uncomfortably warm
We had windows open at times in November
Reviewed on Nov 9, 2026

The Landgrove
Price was $694, price is now $594 per person
$594
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bromley Mountain Ski Resort and Hapgood Pond are located nearby.
The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the hotel was refreshing and the food was VERY good. I thoroughly enjoyed my stay and would highly recommend the inn especially to those who enjoy the atmosphere of well kept historical structures.
Reviewed on Oct 29, 2026

Green Trails Inn
Price was $555, price is now $479 per person
$479
per person
Jan 27 - Jan 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Lebanon (LEB)
Stay at this inn in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Brookfield Free Public Library and Allis State Park are located nearby.
Beautiful bed & breakfast! Located not far from Norwich University! Super clean & welcoming! Cute pub with absolutely amazing food! We enjoyed all our breakfasts & LOVED the dinner that we ordered! Small but quaint town! Would stay again!
Reviewed on Oct 27, 2026

1846 Inn and Tavern
Price was $935, price is now $810 per person
$810
per person
Dec 17 - Dec 21
just found
Roundtrip non-stop flight included
Orlando (MCO) 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.
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026
Plainfield Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Plainfield Vacation Packages 5-7 Night Stays
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$555 Roundtrip, found 3 days ago
$555
Roundtrip
found 3 days ago

Thu, Nov 19 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$565 Roundtrip, found 6 days ago
$565
Roundtrip
found 6 days ago

Thu, Nov 19 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$570 Roundtrip, found 6 days ago
$570
Roundtrip
found 6 days ago

Sat, Nov 21 - Tue, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$575 Roundtrip, found 3 days ago
$575
Roundtrip
found 3 days ago
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