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Top 10 Pittsfield hotels and places to stay

Days Inn by Wyndham Rutland/Killington Area
Room, 1 King Bed, Non Smoking | 1 bedroom, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1006)
"The gentleman that checked us in was great "
The price is £83
includes taxes & fees
10 Aug - 11 Aug
Days Inn by Wyndham Rutland/Killington Area
Best Western Inn & Suites Rutland-Killington
Lobby

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1001)
"Good stay"
The price is £130
includes taxes & fees
1 Sept - 2 Sept
Best Western Inn & Suites Rutland-Killington
Comfort Inn Rutland - Killington
Indoor pool

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1003)
"Great location."
The price is £107
includes taxes & fees
24 Aug - 25 Aug
Comfort Inn Rutland - Killington
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (530)
"Relaxing "
The price is £370
includes taxes & fees
1 Sept - 2 Sept
Woodstock Inn & Resort
Sleep Woodstock Motel
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout curtains

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (506)
"Cozy and comfortable stay!"
The price is £98
includes taxes & fees
18 Aug - 19 Aug
Sleep Woodstock Motel
Cortina Inn
Front of property

Cortina Inn

3.0 star property
6.8 out of 10, (584)
"Staff were extremely helpful all during my stay."
The price is £69
includes taxes & fees
2 Sept - 3 Sept
Cortina Inn
My Place Hotel-Randolph VT
Full-sized fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (243)
"Very nice place to stay would return"
The price is £132
includes taxes & fees
20 Aug - 21 Aug
My Place Hotel-Randolph VT
Brandon Inn
Exterior

Brandon Inn

3.0 star property
8.6 out of 10, Excellent, (497)
"Excellent stay!!"
The price is £111
includes taxes & fees
10 Aug - 11 Aug
Brandon Inn
The Mountain Inn at Killington
Breakfast and dinner served

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (852)
"Clean great views restaurant in house nice staff"
The Mountain Inn at Killington
Hampton Inn Rutland
Exterior

Hampton Inn Rutland

2.5 star property
9.0 out of 10, Wonderful, (930)
"The staff were helpful and morning breakfast very good. "
The price is £125
includes taxes & fees
1 Sept - 2 Sept
Hampton Inn Rutland
Courtyard Middlebury
Exterior

Courtyard Middlebury

3.0 star property
8.8 out of 10, Excellent, (519)
"Good location for hiking and going to Middlebury College "
The price is £118
includes taxes & fees
17 Aug - 18 Aug
Courtyard Middlebury
North Star Lodge and Resort
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets

North Star Lodge and Resort

2.0 star property
8.6 out of 10, Excellent, (1000)
"Good value hotel in an excellent location."
North Star Lodge and Resort
Mountain Meadows Lodge
Lake view

Mountain Meadows Lodge

3.5 star property
9.4 out of 10, Exceptional, (141)
"Just so beautiful!! Everything was so wonderful. Nicest staff ever!! "
The price is £148
includes taxes & fees
10 Aug - 11 Aug
Mountain Meadows Lodge
Mountain Sports Inn
Front of property

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (913)
"Loved the gluten free options in the Breakfast nook"
The price is £77
includes taxes & fees
10 Aug - 11 Aug
Mountain Sports Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (38)
"Superb stay in all ways!"
The price is £246
includes taxes & fees
11 Aug - 12 Aug
Stay At Jimmy's
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.4 out of 10, Good, (1000)
"Views were spectacular "
The price is £114
includes taxes & fees
1 Sept - 2 Sept
Killington Mountain Lodge, Tapestry Collection by Hilton
On The River Inn
Family Suite, 2 Bedrooms | Private kitchen | Microwave

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1001)
"Great location, very quiet with good breakfast choices. "
The price is £210
includes taxes & fees
26 Aug - 27 Aug
On The River Inn
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (31)
"This place was great I cannot say enough about the innkeepers and the staff all in all you'll love it!!"
The price is £140
includes taxes & fees
25 Aug - 26 Aug
Lincoln Inn & Gallery
Summit Lodge
Fireplace

Summit Lodge

3.0 star property
8.6 out of 10, Excellent, (388)
"The Summit Lodge is a gem! Lots of things to do......pool, got tub, billiards, darts, and lawn games. The building is quaint and has a "homey" feel. The owners were super pleasant and friendly. We were there for DH bike racing at Killington and this place was nice and close! We highly recommend this place."
The price is £169
includes taxes & fees
3 Sept - 4 Sept
Summit Lodge
The Mountain Top Inn & Resort
The Jewel | Living area | TV

The Mountain Top Inn & Resort

3.5 star property
9.0 out of 10, Wonderful, (86)
"Great views and food. "
The price is £305
includes taxes & fees
11 Aug - 12 Aug
The Mountain Top Inn & Resort
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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Learn more about Pittsfield

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Top Pittsfield Hotel Reviews

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

10/10 Excellent
"The best thing about this hotel for me was the staff. Everyone was friendly and went above and beyond to make our stay more comfortable. I will also say that this is probably the cleanest hotel pool I have ever seen, and I felt totally comfortable having my kids swim in it. I would definitely stay here again."
Julia 1-night trip
Posted 2 days ago
Best Western Inn & Suites Rutland-Killington

Frequently asked questions

What are the best hotels in Pittsfield that travellers recommend?
Clear River Inn is a charming choice for travellers, earning an excellent review score of 8.8. Nestled in the picturesque setting of Pittsfield, Vermont, this hotel offers stunning river and mountain views that create a serene backdrop for your stay. Guests rave about the premium bedding, ensuring restful nights after days of adventure, and the friendly space that makes it feel like a home away from home.
What are the top pet-friendly hotels in Pittsfield?
Clear River Inn is a charming pet-friendly hotel situated in Pittsfield, Vermont, with a delightful review score of 8.8 from guests who have appreciated its warm atmosphere and attentive service. This inviting property is great for families and travellers with furry companions, allowing dogs and providing amenities like food and water bowls, ensuring a comfortable stay for all. See more pet-friendly hotels in Pittsfield.
What are the best budget hotels in Pittsfield?
Clear River Inn is an inviting choice for budget-conscious travellers seeking a delightful stay in Pittsfield, Vermont. Nestled amidst stunning mountain views, this hotel offers a cozy atmosphere with convenient amenities like complimentary WiFi and free self-parking. Families will appreciate the fully equipped kitchen and premium bedding, great for those looking to prepare meals while enjoying a home-like experience. View all budget hotels in Pittsfield.
When is the best time to go to Pittsfield?
The most popular time to visit Pittsfield is during the summer months, particularly July and August. This is when the weather is at its warmest, with average temperatures ranging from 20 to 25°C. The pleasant climate provides a superb backdrop for outdoor activities, allowing visitors to explore the scenic beauty of the Berkshires, enjoy hiking trails, or relax by the many lakes in the area.

During the peak season from June to August, Pittsfield becomes a hub of activity. Visitors flock to the local parks, enjoy open-air concerts, and participate in various summer festivals that celebrate the region's rich culture and history. This vibrant atmosphere can be quite invigorating, making it an ideal time for families and adventure seekers to immerse themselves in the community spirit.

For those who prefer a quieter experience, consider visiting in September. The weather remains mild, with temperatures comfortably around 18 to 22°C, and you'll encounter fewer crowds. This month also showcases the stunning fall foliage as the leaves change colour, adding a beautiful backdrop to your outdoor excursions. Plus, many local attractions may offer slightly reduced rates during this time, allowing you to enjoy quality experiences at a better value.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Pittsfield hotel for you.
How can I save on a Pittsfield hotel booking with Expedia?
Members always get our best prices. Find our best Pittsfield hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Pittsfield hotel?
Prices for hotels in Pittsfield often vary, but you can find a great deal from £69 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.