Book the Best ROMANTIC Hotels in Chester, VT from CA $182 - Chester Romantic Getaways

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Our top choices for Chester romantic hotels

Coffee/tea maker, fridge, microwave, oven

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

CA $237

CA $514 total

includes taxes & fees

Aug 13 - Aug 14

Coffee/tea maker, microwave, oven, stovetop

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

Ludlow

Justin P.

CA $174

CA $426 total

includes taxes & fees

Aug 17 - Aug 18

4 bedrooms, iron/ironing board, WiFi (free), bed sheets

3. Modern Farm House…minutes to Okemo; 2 King beds!

Mount Holly

Rachel L.

CA $267

CA $695 total

includes taxes & fees

Aug 19 - Aug 20

Shower, eco-friendly toiletries, hair dryer

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

Walpole

Kelly

CA $388

CA $479 total

includes taxes & fees

Aug 13 - Aug 14

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

Walpole

Sean M.

CA $500

CA $618 total

includes taxes & fees

Aug 16 - Aug 17

6. Family Friendly Hilltop House In Putney Vermont

Putney

Susan O.

CA $247

CA $448 total

includes taxes & fees

Sep 1 - Sep 2

7. Cedarbrook Hotel Room 2 Doubles 119

Killington

Leslie

CA $114

CA $182 total

includes taxes & fees

Aug 13 - Aug 14

8. Two Queen Bed Standard Hotel room with outdoor heated pool 201

Killington

Lucy Marshall

CA $114

CA $182 total

includes taxes & fees

Aug 13 - Aug 14

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Top Chester Hotel Reviews

On The River Inn

10/10 Excellent

"Everything was good I cannot complain"

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Perfect"

The Equinox Golf Resort & Spa

8/10 Good

"Good place to stay, but not great."

Kimpton Taconic Hotel by IHG

10/10 Excellent

"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."

Frequently asked questions

Searching for romantic hotels in Chester?

If you and your partner need some romantic time away, we've got just the thing. Our guests also enjoy Chester for its shopping, coffeehouses, and skiing. If you want to explore the area, you might head to DaVallia Art & Accents or Bonnie's Bundles Dolls. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.

What's the best place to stay for a romantic getaway to Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse 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, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.

What is there to do in Chester?

There's nothing better than wandering around 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 coffeehouses, restaurants, and skiing. You might consider a stop 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 go off without a hitch: The closest major airport is Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.

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Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

3. Modern Farm House…minutes to Okemo; 2 King beds!

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

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