Chester Hotel Guide - Romantic Hotels in Chester, Vermont

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Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is €308
includes taxes & fees
14 Apr - 15 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is €271
includes taxes & fees
14 Apr - 15 Apr
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is €190
includes taxes & fees
15 Apr - 16 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is €203
includes taxes & fees
14 Apr - 15 Apr
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is €263
includes taxes & fees
14 Apr - 15 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is €115
includes taxes & fees
1 May - 2 May
Two Double bed Hotel Room with outdoor heated pool 216
Property grounds

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is €332
includes taxes & fees
14 Apr - 15 Apr
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "
United States
Barbara M.
The price is €228
includes taxes & fees
14 Apr - 15 Apr
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is €238
includes taxes & fees
15 Apr - 16 Apr
Family Friendly Hilltop House In Putney Vermont
Exterior

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 reviews)
"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
The price is €116
includes taxes & fees
1 May - 2 May
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 Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Room was perfect (king bed), and big. Hot tub was wonderful after skiing all day and hot, but jets could have been stronger. Staff efficient and very friendly. Location great-10 minutes from Okemo. Will definitely come back!"
Julia 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need some romantic time away, we'd like to help you plan for it. Couples choose Chester for its coffee shops and restaurants. During your trip, you might consider a visit to DaVallia Art & Accents or Bonnie's Bundles Dolls while you're exploring Chester with your significant other. Whether you'd like to lounge around in luxurious bedding or get a couples' massage, you'll be sure to find accommodation in Chester to make for the perfect couples' getaway.
What's the best hotel for couples in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favourite guest house for couples, and features free WiFi and a garden.
When is the best time of year for a romantic getaway to Chester?
If you're hoping to get lost in the rain on your romantic getaway, take a look at these details about year-round temperatures in Chester: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What is there to do in Chester?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all that Chester has to offer. Couples looking for a little of everything will enjoy Chester for its coffee shops, restaurants and skiing. You might consider stopping at DaVallia Art & Accents or Bonnie's Bundles Dolls while you're out and about.
What's the best way to get to Chester and around town during my romantic getaway?
These transportation options in Chester might help your romantic trip get off to a smooth start: The closest major airport is in Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.