Find Romantic Hotels in Chester, VT

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Check availability on Chester Romantic Hotels

Top Chester Romantic Hotels

Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1004)
"Great check in experience and clean, comfortable rooms. "
The price is AED 544
AED 590 total
includes taxes & fees
1 Jul - 2 Jul
Courtyard by Marriott Keene Downtown
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

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

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is AED 814
AED 999 total
includes taxes & fees
22 Jun - 23 Jun
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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, (35)
"Great location, great house, and wonderful breakfast. Would highly recommend and plan to stay there again some day soon."
The price is AED 908
AED 1,120 total
includes taxes & fees
25 Jun - 26 Jun
Entire Farmhouse with lots of open space 15 min north of Keene
Family Friendly Hilltop House In Putney Vermont
Exterior

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (55)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AED 716
AED 1,250 total
includes taxes & fees
27 Jun - 28 Jun
Family Friendly Hilltop House In Putney Vermont
Latchis Hotel
Interior

Latchis Hotel

2.5 star property
8.4 out of 10, Very Good, (745)
"Our stay at the Latchis was wonderful! Super cool to be staying in an old art deco building, and we even took advantage of the movie theater a couple of times. Extremely conveniently located in the center of downtown, just a stone’s throw away from the Amtrak station. "
The price is AED 444
AED 489 total
includes taxes & fees
22 Jun - 23 Jun
Latchis Hotel
Riverside Hotel, Ascend Hotel Collection
Select Comfort beds, in-room safe, desk, blackout drapes

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (572)
"Clean, well decorated, comfortable and spacious rooms. Staff was very courteous and helpful. We will definitely come stay again. "
The price is AED 559
AED 606 total
includes taxes & fees
30 Jun - 1 Jul
Riverside Hotel, Ascend Hotel Collection
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (46)
"The breakfast was excellent and Paul did whatever he could to enhance our stay "
The price is AED 974
AED 1,072 total
includes taxes & fees
29 Jun - 30 Jun
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, (712)
"Very nice area, easy to get to and from. The rooms are spacious. Very comfortable beds!"
The price is AED 592
AED 695 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Inn at Weathersfield
King Room with Spa Bath | Egyptian cotton sheets, premium bedding, memory foam beds

The Inn at Weathersfield

4.0 star property
10.0 out of 10, Exceptional, (62)
"Beautiful historic inn "
The Inn at Weathersfield
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, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is AED 624
AED 1,345 total
includes taxes & fees
23 Jun - 24 Jun
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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.

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need a romantic vacation, we'd like to help you plan for it. Couples choose Chester for its coffeehouses 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 sip a glass of champagne 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 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 fitness center.
How many romantic hotels will we find 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, 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.