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

Romantic Hotels & Resorts in Chester from NZ$231

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Check availability on Chester Romantic Hotels

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Chester romantic hotels

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, (38 reviews)
"Lovely place would definitely book again"
United States
Sean M.
The price is NZ$586
includes taxes & fees
28 June - 29 June
Entire Farmhouse with lots of open space 15 min north of Keene
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)
"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 NZ$523
includes taxes & fees
28 June - 29 June
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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 NZ$645
includes taxes & fees
8 July - 9 July
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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 NZ$562
includes taxes & fees
29 June - 30 June
Family Friendly Hilltop House In Putney Vermont
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 NZ$555
includes taxes & fees
28 June - 29 June
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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, (86 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 NZ$587
includes taxes & fees
29 June - 30 June
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
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 NZ$463
includes taxes & fees
30 June - 1 July
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
The price is NZ$552
includes taxes & fees
30 June - 1 July
Magic Mountain Trailside Condo - Ski In / Ski Out
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 NZ$231
includes taxes & fees
4 July - 5 July
Two Double bed Hotel Room with outdoor heated pool 216
Exterior

Two Double bed Standard Hotel room 217

Two Double bed Standard Hotel room 217
Killington
2.0 out of 10, (1 review)
"Rating Details: The property manager was very unhelpful. The vacation rental was very dirty. I was very unhappy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: Bad experience. Dirty place"
United States
Huong M.
Two Double bed Standard Hotel room 217
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.
View all properties

Top Chester Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"Check in - instructions given ahead of time for our late arrival. Friendly staff. We had a sweet encounter with Amanda - housekeeper/maintenance. She was so down to earth and welcoming energy. Properly was gorgeous and rooms were clean quiet and spacious. Pool - my kids enjoyed! Thanks for tunes Views - amazing"
Nichole 1-night trip
Posted 7 hours ago
The Manchester View

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.