Hotels in Pittsfield

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This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

Where to stay in Pittsfield?

Terrace/patio

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (1 review)
The price is $125
$137 total
includes taxes & fees
Jun 8 - Jun 9
Green Trails Inn
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (580 reviews)
Set in a serene landscape just outside Woodstock, this cozy motel offers the perfect basecamp for Killington and Sugarbush skiing adventures. Clean, peaceful rooms welcome you after days of outdoor exploration. Enjoy free WiFi, parking, and proximity to the Ottaquechee River.
The price is $78
$121 total
includes taxes & fees
Jun 2 - Jun 3
Sleep Woodstock Motel
Lobby sitting area

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,001 reviews)
Slopeside escape with free breakfast and parking, only minutes from Killington and Pico ski resorts. Travelers praise the value and helpful staff at this mountain haven, where outdoor adventures like hiking and cross-country skiing await right outside your door.
The price is $109
$120 total
includes taxes & fees
Jun 2 - Jun 3
Mountain Sports Inn
Breakfast and dinner served

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,000 reviews)
Experience the ultimate ski vacation with slopeside convenience. This mountain retreat offers free breakfast and parking, plus an outdoor pool to relax after hitting the slopes. Near both Killington and Pico Mountain resorts, you'll appreciate the helpful staff and cozy bar/lounge.
The price is $149
$172 total
includes taxes & fees
Jun 2 - Jun 3
The Mountain Inn at Killington
Exterior

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.6 out of 10, Exceptional, (17 reviews)
Escape to this charming Vermont B&B adjacent to a golf course with its own winery and bar. Enjoy free breakfast, Wi-Fi and parking while exploring nearby Neshobe River Winery and Brandon Music. The terrace and garden create peaceful moments between adventures.
The price is $175
$193 total
includes taxes & fees
Jun 3 - Jun 4
Inn at Neshobe River
Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (398 reviews)
Quirky rooms await at this sweet-themed Vermont motel where free WiFi and parking enhance your stay. Near Town Hall Theater and Emma Willard House, guests love the helpful staff and clean accommodations with daily housekeeping service.
The price is $127
$139 total
includes taxes & fees
Jun 2 - Jun 3
Middlebury Sweets Motel
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (572 reviews)
Set in a tranquil environment near Town Hall Theater, this hotel offers American cuisine at the on-site bistro. Rooms include microwaves and refrigerators, while the health club helps you stay fit. The bar, deli, and helpful staff make your Vermont visit relaxing.
The price is $161
$177 total
includes taxes & fees
Jun 2 - Jun 3
Courtyard Middlebury
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (281 reviews)
This peaceful B&B offers a quiet retreat with Victorian charm and lush gardens. Enjoy the on-site restaurant and unwind at the stylish bar after exploring nearby Five Elm Arches. Guests rave about the delicious breakfast and convenient free WiFi and parking.
The price is $175
$193 total
includes taxes & fees
Jun 3 - Jun 4
The Jackson
Lake view

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (221 reviews)
Step into tranquility at this family-friendly retreat near Killington Resort. Enjoy Kent Bistro's dinner offerings and unwind in the sauna or hot tub. With free breakfast, a garden, and highly praised staff, you're perfectly positioned for Pico Mountain adventures.
The price is $142
$181 total
includes taxes & fees
Jun 2 - Jun 3
Mountain Meadows Lodge
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (429 reviews)
Escape to this charming Vermont inn, just minutes from Killington Resort. Enjoy free breakfast before hitting the slopes, or relax in the seasonal outdoor pool after a sauna session. The 24-hour gym and cozy bar offer perfect spots to unwind between mountain adventures.
The price is $205
$223 total
includes taxes & fees
Jun 2 - Jun 3
The Vermont Inn
Free daily buffet breakfast

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,005 reviews)
This Rutland hotel offers an indoor pool and fitness center, plus free breakfast, WiFi, and parking. Located near Diamond Run Mall with easy access to Rutland Station, guests love the helpful staff and morning meal options.
The price is $139
$152 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn Rutland
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (637 reviews)
Located in Brandon, this charming hotel offers a peaceful retreat with a garden, outdoor pool, and terrace. Enjoy the complimentary breakfast, then explore nearby Stephen A Douglas Birthplace while being just a 35-minute drive from Rutland Southern Vermont Regional airport.
The price is $140
$154 total
includes taxes & fees
Jun 2 - Jun 3
Brandon Inn
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
Rustic charm meets outdoor adventure at this Plymouth B&B, just minutes from Okemo Mountain Resort. After tennis matches or mountain excursions, unwind in the outdoor pool and hot tub, then savor a meal at the restaurant.
The price is $230
$251 total
includes taxes & fees
Jun 2 - Jun 3
Echo Lake Inn
Exterior detail

Killington Haus

Killington Haus
2.0 star property
Killington
9.0 out of 10, Wonderful, (44 reviews)
The price is $129
$141 total
includes taxes & fees
Jun 4 - Jun 5
Killington Haus
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (62 reviews)
Wake to complimentary continental breakfast at this charming Woodstock B&B. Enjoy nearby cross-country skiing and snowboarding, then return to free WiFi and parking. Billings Park and Trail and Dana House Museum are just minutes away.
The price is $175
$192 total
includes taxes & fees
Jun 8 - Jun 9
The Vesper
BBQ/picnic area

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (458 reviews)
This business-friendly hotel in Randolph Center offers complimentary WiFi and parking near Whale Dance Sculpture and Montague Golf Club. Just 6 minutes from Randolph Station and 24 minutes from Montpelier airport, with round-the-clock front desk assistance.
The price is $123
$134 total
includes taxes & fees
Jul 2 - Jul 3
My Place Hotel-Randolph VT
Exterior

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (189 reviews)
Surrounded by Vermont's mountains, this cozy inn offers a peaceful stay just minutes from Killington and Pico ski resorts. Enjoy free WiFi and parking, plus a charming picnic area for outdoor relaxation after slopes adventures.
The price is $138
$152 total
includes taxes & fees
Jun 2 - Jun 3
Après Inn Killington
Lobby

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.6 out of 10, (1,001 reviews)
Explore Vermont from this friendly Rutland hotel that offers a complimentary breakfast and free parking. After skiing or hiking, unwind in the indoor pool and sauna. The clean rooms provide a peaceful retreat near Green Mountain Shopping Plaza and Spartan Arena.
The price is $135
$149 total
includes taxes & fees
Jun 3 - Jun 4
Days Inn by Wyndham Rutland/Killington Area
Exterior

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
Tucked away in Vermont's wilderness, these rustic cabins offer fireplaces and full kitchens for a cozy retreat. Explore nearby Robert Frost Farm or hike Skylight Pond Trailhead before unwinding on your private patio surrounded by mountain scenery.
The price is $279
$304 total
includes taxes & fees
Jun 2 - Jun 3
Robert Frost Mountain Cabins
Elite Cabin, 1 King Bed, Sauna | Courtyard view

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (95 reviews)
Escape to this Vermont sanctuary where 8 hot tubs await your relaxation after exploring nearby Otter Valley Winery. Free WiFi and parking complement the rejuvenating sauna, with snowboarding adventures just minutes away.
The price is $180
$203 total
includes taxes & fees
Jun 7 - Jun 8
Emrose Luxury Cabins
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 landmarks in Pittsfield

Pittsfield Town Hall

Pittsfield Town Hall is worth a visit when in central Pittsfield.
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Learn more about Pittsfield

Pittsfield is well-known for its attractions such as Green Mountain National Forest and Roger Clark Memorial Central Library.

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autumn trees reflected in water

Check out reviews of Pittsfield hotels guests love

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Breakfast was plentiful and kitchen area was very clean. Pool and fitness room was clean as well as our room."
Arthur 3-night trip
Posted 12 hours ago
Hampton Inn Rutland

Frequently asked questions

What accommodations do travelers recommend in Pittsfield?
Guests like Killington Mountain Lodge, Tapestry Collection by Hilton, The Mountain Inn at Killington and Mountain Green.
Can I book a refundable accommodation in Pittsfield?
If you need the flexibility to change your travel plans to Pittsfield, most accommodations provide refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Pittsfield if I want a vacation home instead of a hotel?
If you want a good alternative to a hotel, review our selection of 30 vacation homes.
What will the weather in Pittsfield be like during my trip?
The warmest months in Pittsfield are usually July and August with an average temp of 63°F. January and February are the chilliest months when the average temp is 23°F. The rainiest months are July and June.
Why should I book my Pittsfield hotel with Hotels.com?
There are plenty of reasons to book your Pittsfield travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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