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Top Pittsfield Hotels with Free Wifi

Fridge, microwave, oven, stovetop
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne
10.0 out of 10, Exceptional, (1)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
$555 nightly
The price is $621
Dec 9 - Dec 10
Total with taxes and fees
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
$881 nightly
The price is $974
Dec 8 - Dec 9
Total with taxes and fees
The Getaway 4 Bedroom Home
Exterior
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Pittsfield
$737 nightly
The price is $825
Dec 8 - Dec 9
Total with taxes and fees
The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very Good, (1002)
"Clean, great steak house by the hotel"
United States
Caridad
$116 nightly
The price is $128
Dec 10 - Dec 11
Total with taxes and fees
Comfort Inn Rutland - Killington
Deluxe Suite | Individually decorated, desk, blackout drapes, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (547)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
$158 nightly
The price is $174
Dec 7 - Dec 8
Total with taxes and fees
Sleep Woodstock Motel
Exterior
Courtyard Middlebury

Courtyard Middlebury

3.0 star property
Middlebury
8.8 out of 10, Excellent, (543)
"Great hotel, fairly centered , great staff!"
United States
Angelo
$116 nightly
The price is $128
Jan 4 - Jan 5, 2026
Total with taxes and fees
Courtyard Middlebury
Full-size fridge, microwave, stovetop, coffee/tea maker
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (339)
"Awesome staff and great room with Kitchenette"
United States
Mary
$111 nightly
The price is $121
Jan 4 - Jan 5, 2026
Total with taxes and fees
My Place Hotel-Randolph VT
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (966)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
$143 nightly
The price is $158
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn Rutland
Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
Killington
7.4 out of 10, Good, (1001)
"Staff was very helpful and room service was great."
United States
Ankita
$147 nightly
The price is $161
Dec 10 - Dec 11
Total with taxes and fees
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
$151 nightly
The price is $166
Dec 8 - Dec 9
Total with taxes and fees
On The River 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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Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Nice amenities, clean room, welcoming staff. Only 2 min drive from the Snowshed lodge. The on-site brewery and restaurant are pretty great."
Dmitriy 3-night trip
Posted 2 days ago
The Mountain Inn at Killington

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