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Compare 6 Guest Houses in Stockbridge with updated reviews, rates, and availability.

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (122)
"The staff was incredibly helpful. We were shown incredible customer support after a misunderstanding with room bookings. The facility was quiet and clean. I very much enjoyed sitting by the fire at night and the breakfasts in the morning. I would highly recommend this facility to anyone looking to get away for a quiet Vermont weekend!"
The price is SAR 620
SAR 682 total
includes taxes & fees
22 Jan - 23 Jan
The Trailside Inn

Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

9.4 out of 10, Exceptional, (33)
"Overall a great place in a beautiful area next to a skii hill. There were issues with bugs throughout the place when we first arrived. Its important to note there is no mobile service within a mile of this place so make sure to have your wifi and checkin details available. Some parts of the room were dusty and had cobwebs but the owner did have plenty of towels and supplies to make our stay great."
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

Serene dog-friendly guest house with mountain views, fireplace, & firepit

9.2 out of 10, Wonderful, (12)
"More glasses, wine glasses in particular. Better towels. Figure out TV. I used my streaming credentials, if that is what’s expected pls state that. Bedroom TV I could not figure out and did not use."
Serene dog-friendly guest house with mountain views, fireplace, & firepit

110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

8.0 out of 10, Very Good, (5)
"Beds not terrible. Sofa bed very terrible. Great pool. Reasanable price vs quality. Renovated in pass years. Clean place"
The price is SAR 492
SAR 710 total
includes taxes & fees
21 Jan - 22 Jan
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

Inn at Clearwater Pond (Quechee)

3.5 star property
9.4 out of 10, Exceptional, (44)
"Tina was super accommodating and we had a nice get-away. Super convenient location remote feeling but minutes to all of quechee and very close to woodstock. A local farm recommended and we really enjoyed the rural back roads in this most beautiful part of vermont."
Inn at Clearwater Pond (Quechee)

The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Lift Ticket Deals!

The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Lift Ticket Deals!

Salt Ash Inn

3.0 star property
6.0 out of 10, (126)
"Great place, close proximity to Killington. Clean & quiet...Recommend this location."
Salt Ash Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Stockbridge

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (477)
"It was great! Nice spot, great hottub and close to ski slopes"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.