The 10 best inns in Pittsfield, US | Booking.com
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The best inns in Pittsfield

Check out our selection of great inns in Pittsfield

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Clear River Inn and Tavern

Pittsfield

Located in Pittsfield, 11 miles from Killington Peak, Clear River Inn and Tavern provides accommodations with a shared lounge, free private parking, a restaurant and a bar.

P
Philippe
From
Canada
Fiona! She was very kind and helpful. The room was clean and modern. Comfortable. It’s basic but a great basic. Just very sorry I missed the Tavern. Closed on Mondays and Tuesdays.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 201 reviews
Price from
$173.60
1 night, 2 adults

Trailside Inn

Killington (Near Pittsfield)

Located in Killington, 7.4 miles from Killington Peak, Trailside Inn has accommodations with a garden, free private parking, a shared lounge and a tennis court.

D
DiBiasio
From
United States
Here’s an updated review: Fantastic Stay with Incredible Service and Amenities! I recently stayed at the Trailside Inn, and I couldn’t be more pleased with my experience. The inn combines rustic charm with modern comfort, making it the perfect getaway for anyone looking to unwind or explore the area. The rooms were spotless, cozy, and well-equipped. The game room was a fantastic bonus—perfect for relaxing evenings with friends or family. Whether it was playing games or just enjoying the laid-back vibe, it added so much fun to our stay. The lounge area was equally wonderful, with a large TV and a beautiful fireplace that created a warm and inviting atmosphere. It was the perfect spot to relax after a day of outdoor activities. What made the stay even more memorable was the incredible staff. They were genuinely friendly and incredibly helpful, going above and beyond to make sure we had everything we needed. The Trailside Inn is truly a gem, offering everything you could want in a mountain retreat. I can’t wait to come back and would highly recommend it to anyone!
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 8 reviews
Price from
$159.30
1 night, 2 adults

Mountain Sports Inn

Killington (Near Pittsfield)

This rustic ski lodge is located 3 miles from Killington Mountain on the main access road. Offering access to outdoor options for all seasons.

J
John
From
United States
Clean. Quiet. Comfortable. Very reasonably priced. Several small lamps, table and chairs, and plenty of outlets for charging multiple devices. There were no "extras" like coffee maker, fridge, or microwave, but it was the perfect place for what I needed. There was also no AC, but a big box fan was provided in the room and it was so cool out that I opened the window, so being too warm was definitely not an issue. There was a nice medium sized flat screen tv. Breakfast was provided, I didn't partake, but saw that there was fresh fruit, coffee, and bagels and probably more that I didn't see. I will definitely stay here again!
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 706 reviews
Price from
$94
1 night, 2 adults

Greenbrier Inn Killington

Killington (Near Pittsfield)

Located in Killington, this hotel is within a 1.2 mi radius of restaurants and within 4.3 mi of ski areas. Guests are offered discounted elevator tickets to the nearby Killington Ski Resort.

C
Catherine
From
United States
Everything was great - very friendly staff
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 226 reviews
Price from
$169
1 night, 2 adults

Mountain Inn at Killington

Killington (Near Pittsfield)

Located in Killington, 1.1 miles from Killington Peak, Mountain Inn at Killington provides accommodations with an outdoor swimming pool, free private parking, a fitness center and a shared lounge.

M
Maemey
From
United States
The breakfast option was the best part.
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 527 reviews
Price from
$164.68
1 night, 2 adults

Comfort Inn Rutland - Killington

Rutland (Near Pittsfield)

Located directly opposite the Vermont State Fairground, Comfort Inn @ Trolley Square features an indoor heated pool and a hot tub.

A
Ann
From
United States
Location
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 497 reviews
Price from
$120.87
1 night, 2 adults
All inns in Pittsfield

Looking for an inn?

Perfect for rustic breaks in the countryside, an Inn is a small property with basic hotel services and typically traditional decor. Inns are fully licensed and have a bar providing food and drinks in the evening – distinguishing them from country or guest houses.

Inns That Guests Love in Pittsfield

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  • Avg. price/night: $201.43
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 201 reviews
    Everything was great. The room was clean and updated and we enjoyed the restaurant behind the inn. There was a cute telephone booth out front that had the basic necessities. Breakfast items were included and available to grab on the go.
    Guest review by
    Joe
    Family with young children
  • Avg. price/night: $201.43
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 201 reviews
    It was basic but had everything you needed- it was clean and modern. Breakfast was great. Check in and out was made so easy. The tavern was fantastic great food and local beers right onsite
    Guest review by
    Kirstie
    Family with young children
  • Avg. price/night: $201.43
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 201 reviews
    Location and scenery. Staff were awesome Tavern on the premises
    Guest review by
    Susan
    Solo traveler
  • Avg. price/night: $201.43
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 201 reviews
    Very clean and well kept! I wasn’t sure what to expect regarding a telephone booth supply area, but it was really cute and a great idea! Staff were all so nice at the Inn and at the Tavern which had great food!
    Guest review by
    Laura
    Young couple
  • Avg. price/night: $201.43
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 201 reviews
    Spacious room- seemed newly renovated, spotlessly clean, large comfy bed, fluffy towels. Nice lighting and furniture. Breakfast nook was good- cereals, bagels, yoghurt and coffee. Also enjoyed dinner and drinks at the tavern just next door (no driving needed!). Also 10 mins drive to Killington and easy reach to the ski area. Hope to come back!
    Guest review by
    Alison
    Young couple
  • Avg. price/night: $201.43
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 201 reviews
    Continental breakfast had plenty of options that met my needs. The in was in a good location, easy to find. Enjoyed eating at the tavern for dinner. The food and service were excellent!
    Guest review by
    Donna
    Young couple