Pittsfield hotels from HK$849

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Our top choices for Pittsfield hotels

Exterior
Kedron Valley Inn

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (330)
Located in South Woodstock, this inn features the Ransom Tavern for dinner and a cosy bar/lounge with terrace. Free WiFi and parking add convenience while Union Arena and VINS Nature Centre provide nearby exploration options.
"Fantastic stay and staff!"
United States
Carrie
Kedron Valley Inn
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (549)
Located near the Town Hall Theatre, this quiet Middlebury hotel offers American cuisine at Business Bistro. Enjoy a workout in the health club, relax at the bar, and appreciate room conveniences like refrigerators and microwaves.
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is HK$973
HK$1,070 total
includes taxes & fees
13 Jan - 14 Jan
Courtyard Middlebury
Lobby
Middlebury Sweets Motel

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
Located near Town Hall Theatre and Emma Willard House, this cosy Middlebury motel offers free WiFi and parking. Guests praise the helpful staff and clean rooms. Daily housekeeping ensures a comfortable visit.
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is HK$933
HK$1,027 total
includes taxes & fees
12 Jan - 13 Jan
Middlebury Sweets Motel
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (982)
Located minutes from Green Mountain Shopping Plaza, this welcoming hotel offers free WiFi and parking. The indoor pool provides year-round relaxation, while the fitness centre keeps routines on track. Guests consistently praise the helpful staff and hearty breakfast offerings.
"Everything was clean and the staff responsive and friendly. I wish the offerings at breakfast were more substantial. "
United States
Lesley
The price is HK$1,265
HK$1,392 total
includes taxes & fees
14 Jan - 15 Jan
Hampton Inn Rutland
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, (1013)
Situated in central Rutland with easy access to restaurants and activities, this hotel offers an indoor pool and fitness centre. Enjoy American cuisine at SOUTHSIDE STEAKHOUSE, while rooms provide refrigerators and microwaves for added convenience.
"Rooms were clean and comfortable.."
United States
Nimisha
The price is HK$1,093
HK$1,202 total
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn Rutland - Killington
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (666)
"Very quiet and comfortable stay."
United States
James
The price is HK$756
HK$832 total
includes taxes & fees
1 Feb - 2 Feb
Cortina Inn
Lobby
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.4 out of 10, (1004)
This Rutland hotel offers convenient access to Spartan Arena with free WiFi and parking for road trippers. Unwind in the indoor pool after exploring Vermont, or relax in the sauna. Clean rooms provide comfort while helpful staff ensure a pleasant stay.
"Had a great stay"
United States
Jeff
The price is HK$1,151
HK$1,267 total
includes taxes & fees
8 Jan - 9 Jan
Days Inn by Wyndham Rutland/Killington Area
Front of property
The Vermont Inn

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
Experience classic New England hospitality at this charming B&B with a seasonal outdoor pool and 24-hour fitness centre. Just minutes from Killington Resort, guests enjoy free breakfast, WiFi, and parking, plus relaxing sauna and garden terrace spaces.
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is HK$1,997
HK$2,177 total
includes taxes & fees
8 Jan - 9 Jan
The Vermont Inn
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1001)
Quiet retreat near Pico Mountain offers a seasonal outdoor pool, tennis court, and 24-hour fitness centre. Enjoy the free ski shuttle and morning breakfast before hitting the slopes. Helpful staff and clean rooms consistently earn praise from travellers.
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is HK$1,394
HK$1,534 total
includes taxes & fees
15 Jan - 16 Jan
Best Western Inn & Suites Rutland-Killington
Restaurant
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (260)
Victorian charm awaits at this quiet Woodstock B&B where travellers rave about the delicious morning meal. Relax in the garden, enjoy evening drinks at the bar, or explore nearby Union Arena and Five Elm Arches from this peaceful retreat.
"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
Living area
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, (100)
Tucked away in Chittenden, this mountain retreat offers ski-in/ski-out access and a private beach. Enjoy cross-country skiing, sledding, or tennis, followed by American cuisine at Highlands Dining Room. Lefferts Pond and the resort's outdoor pool await.
"Room was comfy and clean. The view from the window was gorgeous. The whole resort was so quaint, warm and beautiful. "
United States
Ping
The price is HK$2,530
HK$2,758 total
includes taxes & fees
11 Jan - 12 Jan
The Mountain Top Inn & Resort
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
Surrounded by picturesque Vermont landscapes, this luxury resort offers a tranquil escape with an 18-hole golf course and full-service spa. Enjoy 4 restaurants, indoor and outdoor pools, plus easy access to local covered bridges and theatres.
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is HK$2,484
HK$3,074 total
includes taxes & fees
19 Jan - 20 Jan
Woodstock Inn & Resort
BBQ/picnic Area
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (361)
Just off I-89 in Randolph Centre, this hotel offers convenient amenities including complimentary WiFi and self parking. The 24-hour front desk ensures assistance anytime while Whale Dance Sculpture and Montague Golf Club await nearby.
"Friendly staff, clean, very comfortable room."
United States
Jennifer
The price is HK$825
HK$899 total
includes taxes & fees
25 Jan - 26 Jan
My Place Hotel-Randolph VT
Exterior
Echo Lake Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
Set in Plymouth, this country inn offers tennis, a hot tub, and outdoor pool. Just 10 minutes from Okemo Mountain Resort and near Echo Lake, guests enjoy complimentary breakfast, WiFi, and parking.
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
The price is HK$2,021
HK$2,202 total
includes taxes & fees
7 Jan - 8 Jan
Echo Lake Inn
Private kitchen
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (553)
Enjoy a peaceful retreat near Killington and Sugarbush ski resorts. This well-maintained motel offers clean rooms and friendly staff in a beautiful Vermont setting. Free WiFi and parking make it easy to explore Ottaquechee River and local hiking trails.
"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
The price is HK$568
HK$1,111 total
includes taxes & fees
21 Jan - 22 Jan
Sleep Woodstock Motel
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (899)
Tucked in charming Woodstock, this welcoming hotel provides complimentary WiFi, parking, and bicycle rentals for exploring nearby trails. Guests praise the helpful staff and spotless rooms, with Billings Park and Red Wagon Toy Company just moments away.
"Wonderful place to stay!"
United States
Robin
The price is HK$920
HK$1,093 total
includes taxes & fees
11 Jan - 12 Jan
The Shire Woodstock
Interior
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52)
Surrounded by seasonal adventure, this charming 3-star B&B offers complimentary continental breakfast, WiFi, and parking. Winter enthusiasts will love the cross-country skiing and snowboarding options, with Billings Park and Dana House Museum just minutes away.
"Charming bed and breakfast"
United States
Nicholas
The price is HK$1,169
HK$1,286 total
includes taxes & fees
14 Jan - 15 Jan
The Vesper
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, (1006)
Discover a tranquil retreat near the train station in Woodstock featuring an indoor pool, hot tub, and on-site 506 Bistro and Lounge. Guests love the helpful staff, complimentary breakfast, and convenient access to Union Arena Community Centre.
"Brilliant stay"
United States
Enrico
On The River Inn
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
This cosy Woodstock B&B offers free continental breakfast daily, plus convenient WiFi and parking. Explore nearby attractions like Billings Park and Trail or Red Wagon Toy Company, then return to this welcoming retreat.
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is HK$1,939
HK$2,132 total
includes taxes & fees
7 Jan - 8 Jan
Stay At Jimmy's
Lobby sitting area
Lincoln Inn & Gallery

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (58)
Escape to this cosy Woodstock inn with complimentary WiFi and parking. Near Ottaquechee River and Union Arena Community Centre, you'll appreciate the warm lobby fireplace. Snowmobiling adventures start right on the property for winter thrills.
"A very pleasant VT stay at a reasonable price."
United States
Sean
The price is HK$981
HK$1,079 total
includes taxes & fees
7 Jan - 8 Jan
Lincoln Inn & Gallery
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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Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.
See properties

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
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Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"yes"
phillip 1-night trip
Posted 3 days ago
My Place Hotel-Randolph VT

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is HK$825 per night from 25 Jan to 26 Jan
HK$825
HK$899 total
25 Jan - 26 Jan
includes taxes & fees
9.2/10 Wonderful! (361 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Killington Mountain Lodge, Tapestry Collection by Hilton and The Mountain Inn at Killington. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Killington, Vermont Ski House w/ Hot Tub and Sauna: This holiday home rental outside Pittsfield is located in the mountains, and has a balcony, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
What's the best dog-friendly accommodation option in Pittsfield?
Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.
What are some accommodation options with pools in Pittsfield?
Comfort Inn Rutland - Killington: Features continental, an indoor pool and free self parking. The Mountain Inn at Killington and Woodstock Inn & Resort are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.
How is it to stay in Pittsfield?
Visitors can enjoy all that Pittsfield has to offer, including the bars and restaurants. This city also attracts tourists with its welcoming locals. A top sight in the area is Killington Resort. In Pittsfield, there are 41 hotels and other accommodation options to choose from. Find out more about Pittsfield.
What are the top places to visit in Pittsfield?
Favourite places to visit include Green Mountain National Forest, Roger Clark Memorial Central Library and Pittsfield Town Hall. Additionally, you'll find Killington Resort in the area. Take a look at what more there is to see and do in Expedia's Pittsfield guide.
What's the seasonal weather in Pittsfield?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.

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