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

Chester Hotel Guide - Romantic Hotels in Chester, Vermont

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Our top choices for Chester romantic hotels

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
9.6 out of 10, Exceptional, (9 reviews)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
The price is €335
includes taxes & fees
20 Jul - 21 Jul
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds

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

Entire Farmhouse with lots of open space 15 min north of Keene
Walpole
10.0 out of 10, Exceptional, (39 reviews)
"Lovely place would definitely book again"
United States
Sean M.
The price is €345
includes taxes & fees
12 Aug - 13 Aug
Entire Farmhouse with lots of open space 15 min north of Keene
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (61 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is €285
includes taxes & fees
15 Jul - 16 Jul
Family Friendly Hilltop House In Putney Vermont
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)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is €314
includes taxes & fees
14 Jul - 15 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Fridge, microwave, oven, stovetop

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (112 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is €362
includes taxes & fees
14 Jul - 15 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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, (109 reviews)
"Great location, "
United States
Bryan R J.
The price is €304
includes taxes & fees
12 Aug - 13 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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, (87 reviews)
"Beautiful and immaculately clean home located within walking distance to downtown, shopping, and restaurants. Very quiet location. We felt safe and comfortable at this home. Property has 3 bedrooms and 5 very comfortable beds. The attic bedroom has 3 single beds which is handy for larger families. Loved sitting around the fire pit and was pleased that our yard was separated from the neighbors. Thank you so much for sharing your hospitality."
United States
Kristen
The price is €396
includes taxes & fees
14 Jul - 15 Jul
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is €290
includes taxes & fees
20 Jul - 21 Jul
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

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

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is €428
includes taxes & fees
19 Jul - 20 Jul
Modern Farm House…minutes to Okemo; 2 King beds!
Smart TV, fireplace, video games, DVD player

Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (44 reviews)
"Awesome home. Had a great time with the family. Owners were easy to get in touch with."
United States
william k.
Summer Escape Near Lakes, Trails & Mt Snow
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

On The River Inn

On The River Inn

10/10 Excellent
"Great hotel! Our room was spacious and we loved having a full size fridge and mini-kitchen. Insanely loved the bath products (sorry, I love that kind of thing!). We had a great dinner at the restaurant which has a wonderful vibe and friendly staff. When we checked in, the front desk staff forgot to mention breakfast was included (clearly I had forgotten, too)-- took me 2 days to realize that! Breakfast was great. Another plus-- the gigantic backyard/meadow adjacent to the river is stunning and smores at night were an added bonus! They do a great job creating a hotel that is perfect for families, mountain bike travelers, horse show folks, couples getaways. Hard for one place to cover all that. I had booked via an online site which I thought included all fees but there was a small daily added cost. Overall though our total expenditure was LESS than other area hotels and really, this was so beautiful, immaculate, delish and otherwise very hospitable! We will be back!"
Audra Michael 3-night trip
Posted 13 hours ago
On The River Inn

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need a romantic holiday, we'd like to help you plan for it. Our guests also enjoy Chester for its shopping, coffee shops and skiing. If you want to explore the area, you might head to DaVallia Art & Accents or Bonnie's Bundles Dolls. If you'd like to stay close to a certain attraction, you can sort properties by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
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.