Search Hotels with Restaurant in Pittsfield

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Check availability on Pittsfield Hotels with Restaurant

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Pittsfield hotels with a restaurant

Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (546)
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is 3.109.117 ₫
3.420.028 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
Lobby
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1004)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is 3.780.150 ₫
4.158.165 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn Rutland - Killington
Premium Suite, Multiple Beds | Balcony
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (986)
"Great place, good rates"
United States
Alexander
The price is 3.394.635 ₫
3.734.099 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Mountain Sports Inn
Hallway
On The River Inn

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
The price is 5.078.795 ₫
6.551.646 ₫ total
includes taxes & fees
22 Dec - 23 Dec
On The River Inn
Restaurant
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Garden
North Star Lodge and Resort

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1001)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (181)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is 5.760.354 ₫
6.994.264 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Meadows Lodge
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (398)
"The staff was really great and helpful. There are a number of very cool public spaces to enjoy"
United States
George
The price is 4.570.915 ₫
5.028.008 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Summit Lodge
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (965)
"Great place to stay!"
United States
Stephen
The price is 6.134.026 ₫
7.085.049 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Mountain Inn at Killington
The Jewel | Living area | TV
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (96)
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
The price is 8.552.375 ₫
9.322.089 ₫ total
includes taxes & fees
22 Dec - 23 Dec
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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Top Pittsfield Hotel Reviews

Frequently asked questions

How much do hotels with dining in Pittsfield cost?
Prepare to pay between 3.420.028 ₫ and 9.322.089 ₫ per night for hotels in Pittsfield. A perfect stay with a restaurant, or one with access to epic foodie experiences, is only a few clicks away with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with dining in Pittsfield?
Pick from multiple hotels with dining in Pittsfield with a total average guest review rating of 8.9. Greenbrier Inn will place you near some tasty foodie experiences. This popular 2-star property also features pool sun loungers and a swimming pool. Mountain Meadows Lodge is another recommended option with dining. It has a 3.5-star rating and amenities such as a lake view and a firepit.
How many hotels with restaurants are there in Pittsfield?
There are 2 hotels with restaurants in Pittsfield. Whether you're holidaying with the family or organising a weekend escape with some pals, Expedia will help you find the ideal place.
What are the best cheap hotels with dining in Pittsfield?
With hotels with dining starting at just 3.420.028 ₫ per night, you'll have more cash in your pocket to splurge on terrific culinary experiences in Pittsfield! Greenbrier Inn is an affordable option that features amenities such as individually decorated rooms and pool sun loungers. Alternatively, taste the flavours of this destination from Mountain Sports Inn. A sauna and individually decorated rooms are among this stay's conveniences. If you want to hold on to your hard-earned cash and still see the best of Pittsfield, add a couple of awesome free attractions to your to-do list. Fire Tower and Lefferts Pond will keep you busy. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with dining in Pittsfield?
Many travellers after a family-friendly hotel with dining in Pittsfield go for Mountain Meadows Lodge. With a 3.5-star rating and amenities like complimentary breakfast and a firepit, it'll get your crew's nod of approval. North Star Lodge and Resort is a 2-star stay that will also put you within reach of some tasty food experiences. A sauna and laundry facilities help make it a comfortable base for your family holiday. After checking in and kicking back together in your comfy new digs, it's time to start sightseeing. Fire Tower and Pico Mountain at Killington Ski Resort are fun family-friendly attractions in Pittsfield.
Why book your hotel with restaurants in Pittsfield with Expedia?
Expedia makes it a cinch to find your ideal hotel with restaurants in Pittsfield. Make the most of our filters to search for properties with a restaurant on-site. If you're sticking to a budget, select how much you want to spend and the star rating of your hotel. We'll help you find the perfect fit whatever your tastes or bank balance.
How can I find cheap hotels with restaurants in Pittsfield?
Expedia can help you narrow your search for cheap hotels with restaurants in Pittsfield. Use our filter tools to lock in properties with restaurants or satisfying extras, like included breakfast and lunch. You can also choose how much you want to spend per night and your preferred hotel star rating to cut costs.