Chittenden Hotels

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Our top choices for Chittenden hotels

The Jewel | 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, (96)
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.
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
The price is €301
includes taxes & fees
24 Dec - 25 Dec
The Mountain Top Inn & Resort
Exterior
Middlebury Inn

Middlebury Inn

Middlebury Inn
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (1004)
Located in the heart of Middlebury, this historic hotel offers a peaceful atmosphere near Town Hall Theatre. The full-service spa provides massages and wraps, while Morgans Tavern serves local cuisine. Free WiFi and parking complement the clean rooms and helpful staff.
"Perfect New England Inn right in the heart of town."
United States
LaTascha
The price is €121
includes taxes & fees
4 Jan - 5 Jan 2026
Middlebury Inn
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (546)
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 €117
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
Property grounds
Swift House Inn

Swift House Inn

Swift House Inn
3.0 star property
Middlebury
9.4 out of 10, Exceptional, (323)
Located in Middlebury, this welcoming hotel offers Jessica's restaurant for dinner and a relaxing sauna and steam room. Free breakfast, WiFi, and parking enhance your stay. National Museum of the Morgan Horse and Danforth Pewter are nearby attractions.
"Great place!! Excellent breakfast. Great restaurant with Friendly staff.Quaint Vermont Inn with nice rooms. "
United States
Doug
Swift House Inn
Classic Room, 2 Queen Beds
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 €92
includes taxes & fees
30 Dec - 31 Dec
Middlebury Sweets Motel
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 €336
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Inn & Resort
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
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 Shire Woodstock
Terrace/patio
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1001)
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.
"Rearaurant staff was top notch. "
United States
Daniel
The price is €335
includes taxes & fees
29 Dec - 30 Dec
On The River Inn
Room, 1 King Bed, Non Smoking
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, (1003)
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.
"The food "
United States
Elijah
The price is €138
includes taxes & fees
6 Jan - 7 Jan 2026
Days Inn by Wyndham Rutland/Killington Area
Deluxe Suite
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
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 €131
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1009)
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.
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is €134
includes taxes & fees
6 Jan - 7 Jan 2026
Comfort Inn Rutland - Killington
Interior
Lincoln Inn & Gallery

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (57)
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 €178
includes taxes & fees
26 Dec - 27 Dec
Lincoln Inn & Gallery
Front of property
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
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
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, (1005)
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 €167
includes taxes & fees
6 Jan - 7 Jan 2026
Best Western Inn & Suites Rutland-Killington
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 €233
includes taxes & fees
6 Jan - 7 Jan 2026
Stay At Jimmy's
Economy Room
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
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 €174
includes taxes & fees
30 Dec - 31 Dec
The Vesper
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (972)
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.
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is €154
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Rutland
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (658)
"Very quiet and comfortable stay."
United States
James
The price is €111
includes taxes & fees
24 Dec - 25 Dec
Cortina Inn
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 €238
includes taxes & fees
25 Dec - 26 Dec
The Vermont Inn
Room, Lake View (Lodge)
Lake Bomoseen Lodge

Lake Bomoseen Lodge

Lake Bomoseen Lodge
3.5 star property
Bomoseen
9.4 out of 10, Exceptional, (865)
"Have stayed here quite a few times and every time everything is absolutely amazing!"
United States
Beth
The price is €127
includes taxes & fees
6 Jan - 7 Jan 2026
Lake Bomoseen Lodge
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 Chittenden attractions

Lefferts Pond

Explore the lovely green spaces of Lefferts Pond and enjoy the ski slopes in Chittenden. Discover the mountain views while you're in the area.
See properties

Learn more about Chittenden

Nestled in Vermont's Green Mountains, Chittenden offers pristine hiking trails around Chittenden Reservoir and the chance to spot wildlife. Rent a kayak to explore the reservoir's calm waters or visit nearby Killington for mountain biking adventures in summer.

See all hotels in Chittenden
Lefferts Pond near Killington Vermont in Autumn

Top Chittenden Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Rearaurant staff was top notch. "
Daniel 1-night trip
Posted 1 day ago
On The River Inn

More cheap stays in Chittenden

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is €94 per night from 18 Jan to 19 Jan
€94
18 Jan - 19 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (346 reviews)

Frequently asked questions

Where is the best place to stay in Chittenden?
Based on our traveller data, The Mountain Top Inn & Resort is one of the top choices for your stay. This resort offers a private beach and a restaurant. Two other choices for your stay in the area are Comfort Inn Rutland - Killington and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Chittenden.
What are some of the best holiday rentals that Chittenden has to offer?
Water front home with large two tiered deck! 2 bathrooms 😂: This holiday home rental outside Chittenden is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all vacation rentals in Chittenden.
If I need to cancel my hotel reservation in Chittenden, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chittenden.
What's the best dog-friendly place to stay in Chittenden?
The Mountain Top Inn & Resort is a top dog-friendly resort, and offers a private beach along with TVs for its human guests. See more pet-friendly hotel accommodations in Chittenden.
What's the best hotel to stay near the beach in Chittenden?
The Mountain Top Inn & Resort is a top resort located on the beach . See more stays near the beach in Chittenden.
What's the best accommodation option for a trip to the slopes in Chittenden?
The Mountain Top Inn & Resort is a top resort for a winter getaway, and features ski-in/ski-out access and satellite TVThis resort is located 22 minutes by car from Pico Mountain at Killington Ski Resort. See all ski hotels in Chittenden.
What are some accommodation options with pools in Chittenden?
The Mountain Top Inn & Resort: Features a private beach, a seasonal outdoor pool and a sauna. Comfort Inn Rutland - Killington and The Mountain Inn at Killington are a couple of other choices with an on-site pool. View all hotels with pools in Chittenden.
What's it like staying in Chittenden?
Visitors can enjoy all that Chittenden has to offer, including the ski areas, mountain views and lake views. Tourists can also enjoy the city's bars and restaurants. A top sight in the area is Killington Resort. In Chittenden, there are 15 hotels and other accommodation options to choose from. Find out more about Chittenden.
What should I see while I'm in Chittenden?
The picturesque setting of Green Mountain National Forest and Lefferts Pond exemplify the area's natural beauty. Additionally, you'll find Killington Resort in the area. Take a look at what more there is to see and do in Expedia's Chittenden guide.
What's the seasonal weather in Chittenden?
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 Chittenden are January, March, November and December, with each month seeing an average of 33 cm of snowfall.

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