Find Romantic Hotels in Pittsfield, VT

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Check availability on Pittsfield Romantic Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Pittsfield Romantic Hotels

Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
Killington
7.4 out of 10, Good, (1000)
"It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared. "
United States
Cynthia
The price is SAR 551
SAR 606 total
includes taxes & fees
9 Dec - 10 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 star property
Rutland
8.8 out of 10, Excellent, (1000)
"The staff is wonderful! Friendly, helpful and they work very hard. The room was clean but a little small for our liking so we will make sure to book a larger room next time. You can't beat the location. It's so close to everything!"
United States
Jennifer
The price is SAR 605
SAR 665 total
includes taxes & fees
11 Dec - 12 Dec
Best Western Inn & Suites Rutland-Killington
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 star property
Killington
9.2 out of 10, Wonderful, (952)
"Great place to stay!"
United States
Stephen
The price is SAR 706
SAR 816 total
includes taxes & fees
7 Dec - 8 Dec
The Mountain Inn at Killington
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (563)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is SAR 418
SAR 459 total
includes taxes & fees
7 Dec - 8 Dec
Brandon Inn
Room, 1 King Bed, Non Smoking | Desk, blackout drapes, iron/ironing board, free cribs/infant beds
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)
"The food "
United States
Elijah
The price is SAR 443
SAR 488 total
includes taxes & fees
8 Dec - 9 Dec
Days Inn by Wyndham Rutland/Killington Area
Lounge
Greenbrier Inn

Greenbrier Inn

2.0 star property
Killington
9.4 out of 10, Exceptional, (645)
"It was a very quaint inn in a gorgeous location."
United States
ELIZABETH
Greenbrier Inn
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (552)
"Highly recommend stay here"
United States
Margie
The price is SAR 1,272
SAR 1,565 total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Front of property
The Vermont Inn

The Vermont Inn

3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
"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 SAR 760
SAR 828 total
includes taxes & fees
8 Dec - 9 Dec
The Vermont Inn
Fireplace
Summit Lodge

Summit Lodge

3.0 star property
Killington
8.6 out of 10, Excellent, (396)
"When we first arrived it felt really old and I was wondering what I had booked. Then, the place grew on me as I explored the hotel. I could see this as being really fun in the winter and with a group."
United States
Wendy
The price is SAR 652
SAR 717 total
includes taxes & fees
18 Dec - 19 Dec
Summit Lodge
Property grounds
Two Double Bed Standard Hotel Room with outdoor heated pool 101

Two Double Bed Standard Hotel Room with outdoor heated pool 101

Killington
8.2 out of 10, Very Good, (17)
"Loved this lodging. Super fun outdoorsy place. Enjoyed the warm pool and grills and picnic table area. Liked the coffee in mornings in the office. "
United States
Dr Arun
Two Double Bed Standard Hotel Room with outdoor heated pool 101
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"The food "
Elijah 2-night trip
Posted 3 days ago
Days Inn by Wyndham Rutland/Killington Area

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Frequently asked questions

Searching for romantic hotels in Pittsfield?
If you and your partner need a romantic escape, we'd like to help you plan for it. If you want to explore the area, you might head to Green Mountain National Forest. If you'd like to stay close to a particular destination, you can sort by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Pittsfield?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Pittsfield: The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.
What is there to do in Pittsfield?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Pittsfield. Green Mountain National Forest is one of the local sights that might be worth a stop.
What's the best way to get to Pittsfield and around town during my romantic getaway?
This information about transportation options in Pittsfield might help your romantic trip get off to a smooth start: To get to Pittsfield, book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is the closest major airport, located 18.1 mi (29.2 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.