Find Romantic Hotels in Pittsfield, VT

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Check availability on Pittsfield Romantic Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Pittsfield Romantic Hotels

Best Western Inn & Suites Rutland-Killington
Lobby

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1001)
"Fantastic place to stay. It was clean, comfortable and inviting. Staff were friendly and hospitable. Would stay here again! "
The price is AED 592
AED 651 total
includes taxes & fees
21 Oct - 22 Oct
Best Western Inn & Suites Rutland-Killington
Brandon Inn
Exterior

Brandon Inn

3.0 star property
8.8 out of 10, Excellent, (528)
"Quaint hotel…..love the history "
The price is AED 409
AED 449 total
includes taxes & fees
19 Oct - 20 Oct
Brandon Inn
Greenbrier Inn
32-inch flat-screen TV with cable channels, TV

Greenbrier Inn

2.0 star property
9.4 out of 10, Exceptional, (618)
"Wonderful staff "
Greenbrier Inn
Emrose Luxury Cabins
Family Cabin, 2 Queen Beds | Blackout drapes, free WiFi, bed sheets

Emrose Luxury Cabins

2.0 star property
9.0 out of 10, Wonderful, (51)
"It’ll be nice when it’s all finished to work in progress"
The price is AED 681
AED 770 total
includes taxes & fees
2 Oct - 3 Oct
Emrose Luxury Cabins
The Mountain Top Inn & Resort
The Jewel | Living area | TV

The Mountain Top Inn & Resort

3.5 star property
9.0 out of 10, Wonderful, (91)
"We had a great time! Gorgeous view and everybody was super friendly and helpful!"
The price is AED 1,084
AED 1,181 total
includes taxes & fees
1 Nov - 2 Nov
The Mountain Top Inn & Resort
Days Inn by Wyndham Rutland/Killington Area
Room, 1 King Bed, Non Smoking | Desk, blackout drapes, iron/ironing board, free cribs/infant beds

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1015)
"The staff was fantastic the room was clean and they allowed me to bring my dog "
The price is AED 381
AED 419 total
includes taxes & fees
21 Oct - 22 Oct
Days Inn by Wyndham Rutland/Killington Area
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (534)
"Clean room. Staff very polite and helpful "
The price is AED 1,870
AED 2,218 total
includes taxes & fees
30 Oct - 31 Oct
Woodstock Inn & Resort
The Lilac Inn
Exterior

The Lilac Inn

3.5 star property
9.6 out of 10, Exceptional, (207)
"I love staying at the Lilac Inn when visiting family in the area. "
The price is AED 782
AED 860 total
includes taxes & fees
8 Oct - 9 Oct
The Lilac Inn
Summit Lodge
Fireplace

Summit Lodge

3.0 star property
8.6 out of 10, Excellent, (390)
"Love the old ski lodge feel and the layout of the hotel"
The price is AED 754
AED 829 total
includes taxes & fees
9 Oct - 10 Oct
Summit Lodge
Killington Grand Hotel
Exterior

Killington Grand Hotel

3.5 star property
8.8 out of 10, Excellent, (180)
"Fantastic....Perfect place for a fall getaway."
Killington Grand Hotel
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.
View all properties

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."
Patricia 1-night trip
Posted 6 days ago
The Mountain Inn at Killington

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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.