Search Deals onBolton Landing Vacation Packages
Bolton Landing Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Bentley House Bed and Breakfast
Price was $587, price is now $510 per person
$510
per person
Jan 6 - Jan 10
found 17 hours 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

Lake Bomoseen Lodge
Price was $743, price is now $591 per person
$591
per person
Dec 17 - Dec 21
found 1 day ago
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.
Beautiful and comfortable lodge with a wonderful lake view and stunning scenery, staff was very helpfull !
Reviewed on Nov 12, 2026

Mountain Green Resort
Price was $1,686, price is now $1,342 per person
$1,342
per person
Jan 6 - Jan 10
found 17 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 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
found 1 day ago
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

Days Inn by Wyndham Rutland/Killington Area
Price was $835, price is now $740 per person
$740
per person
Jan 6 - Jan 10
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Shopping Plaza and Spartan Arena are located nearby.
Spacious updated rooms. LOVE the vinyl vs. carpeted floors in the rooms, much cleaner. Breakfast needs more healthy options... low fat or fat free yogurts/milk, lower sugar options, eggs.
Overall, a great overnight stay.
Reviewed on Nov 7, 2026

The Suites at Killington Center
Price was $1,307, price is now $1,177 per person
$1,177
per person
Dec 16 - Dec 18
found 2 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Landgrove
Price was $1,880, price is now $1,738 per person
$1,738
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop 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

Emrose Luxury Cabins
Price was $740, price is now $690 per person
$690
per person
Jan 6 - Jan 10
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Stephen A Douglas Birthplace and Judith Reilly Gallery are located nearby.
Bolton Landing Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Bolton Landing Vacation Packages 5-7 Night Stays
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