Chester Hotel Guide - Romantic Hotels in Chester, Vermont

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Check availability on Chester Romantic Hotels

Top Chester Romantic Hotels

Entire Farmhouse with lots of open space 15 min north of Keene
Exterior detail

Entire Farmhouse with lots of open space 15 min north of Keene

10.0 out of 10, Exceptional, (36)
"Great location, great house, and wonderful breakfast. Would highly recommend and plan to stay there again some day soon."
The price is €267
includes taxes & fees
13 Aug - 14 Aug
Entire Farmhouse with lots of open space 15 min north of Keene
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (49)
"The folks were nice and accommodating. The breakfast was absolutely fantastically delicious. We would recommend this B&B to all our family and friends."
The price is €279
includes taxes & fees
28 Aug - 29 Aug
Inn on Putney Road
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (730)
"Great place great scenery amazing staff"
The price is €117
includes taxes & fees
4 Sept - 5 Sept
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (160)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is €322
includes taxes & fees
25 Aug - 26 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Pointe at Castle Hill Resort
Indoor pool

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (859)
"Will definitely stay here again! Very clean room nice and quiet and staff were very personable!"
The price is €156
includes taxes & fees
13 Aug - 14 Aug
Pointe at Castle Hill Resort
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (96)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
The price is €241
includes taxes & fees
13 Aug - 14 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
The price is €198
includes taxes & fees
25 Aug - 26 Aug
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Deerhill Inn
Exterior

Deerhill Inn

3.5 star property
9.6 out of 10, Exceptional, (219)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is €194
includes taxes & fees
24 Aug - 25 Aug
Deerhill Inn
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV, DVD player

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

9.4 out of 10, Exceptional, (24)
"Great location for ski in ski out unit on 1st floor. Steps away from clock tower base and lift. Easy access to post ski fun for drink/dining super close The Loft or The Bull both 2 mins walk from condo. "
The price is €193
includes taxes & fees
17 Aug - 18 Aug
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

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

9.4 out of 10, Exceptional, (16)
"Highly recommend clean beautiful stay!"
The price is €229
includes taxes & fees
1 Sept - 2 Sept
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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.

Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"I needed to be close to Rutland for a biz meeting and this was a very worthy extra drive and wonderful property.... Will be back !"
Erik 1-night trip
Posted 3 days ago
The Equinox Golf Resort & Spa

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 fitness centre.
How many romantic hotels are there in Chester?
Expedia has 5 romantic Chester hotels for you both to enjoy.
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.