Find Romantic Hotels in Pittsfield, VT from $124

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Check availability on Pittsfield Romantic Hotels

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Dec 4 - Dec 5
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Dec 5 - Dec 6
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Dec 5 - Dec 7
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Dec 12 - Dec 14

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
$147 nightly
The price is $161
Dec 9 - Dec 10
Total with taxes and fees
Killington Mountain Lodge, Tapestry Collection by Hilton
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (564)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
$112 nightly
The price is $124
Dec 11 - Dec 12
Total with taxes and fees
Brandon Inn
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
$161 nightly
The price is $177
Dec 11 - Dec 12
Total with taxes and fees
Best Western Inn & Suites Rutland-Killington
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
$118 nightly
The price is $130
Dec 7 - Dec 8
Total with taxes and fees
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
$172 nightly
The price is $188
Dec 18 - Dec 19
Total with taxes and fees
Greenbrier Inn
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, (953)
"Great place to stay!"
United States
Stephen
$219 nightly
The price is $241
Dec 7 - Dec 8
Total with taxes and fees
The Mountain Inn at Killington
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
$379 nightly
The price is $417
Dec 16 - Dec 17
Total with taxes and fees
Woodstock Inn & Resort
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
$193 nightly
The price is $212
Dec 11 - Dec 12
Total with taxes and fees
Summit Lodge
The Jewel | Living area | TV
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 star property
Chittenden
9.0 out of 10, Wonderful, (95)
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
$325 nightly
The price is $354
Dec 6 - Dec 7
Total with taxes and fees
The Mountain Top 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
$225 nightly
The price is $245
Dec 7 - Dec 8
Total with taxes and fees
The Vermont Inn
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

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.

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