Title: Book the Best ROMANTIC Hotels in Chester, VT from CA $250  - Chester Romantic Getaways | Expedia.ca

[Hotels in Chester](https://expedia.ca/Chester-Hotels.d89014.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d89014.Travel-Guide-VacationRentals)[Things to do in Chester](https://expedia.ca/Things-To-Do-In-Chester.d89014.Travel-Guide-Activities)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d89014.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d89014.Destination-Travel-Guides)

![aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/89014/92c0e546-2b37-46d6-9961-c387fdf435b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Chester Romantic Hotels

Tonight

[Mar 11 - Mar 12](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-11&endDate=2026-03-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Tomorrow

[Mar 12 - Mar 13](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-12&endDate=2026-03-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

This weekend

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

Next weekend

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=89014&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic)

## Our top choices for Chester romantic hotels

![Exterior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/62670e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/b81f74eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/306e8880.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27120000/27117200/27117112/c5d0a9bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Fully Renovated One-Room Schoolhouse on 22+ acres

[](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information)

Grafton

9.6/10

Exceptional

(167 reviews)

"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Philip

CA $231

CA $502 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Grafton-Hotels-Charming-Fully-Renovated-One-Room-Schoolhouse-On-22-Acres.h27117112.Hotel-Information)

![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

Walpole

10/10

Exceptional

(8 reviews)

"Beautiful cozy cottage. Very clean. Wonderful host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gloria A.

CA $264

CA $325 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w1125h1933x0y49-6292efb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w960h638x0y1-6a5c7328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Family Friendly Hilltop House In Putney Vermont

[](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

Putney

9.4/10

Exceptional

(59 reviews)

"The host and her daughter were lovely and kind and very quick with all communication."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan O.

CA $209

CA $397 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/790c70e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/82f89163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/1d0d61a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/62000000/61640000/61636400/61636331/191f5e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information)

Ludlow

9.0/10

Wonderful

(25 reviews)

"Great rate for a place with all the basics!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Macgregor

CA $151

CA $364 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Ludlow-Hotels-Downtown-Condo-W-Electric-Fireplace.h61636331.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/04000126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/dec25c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/64548e51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/37000000/36780000/36778100/36778065/5200a28c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

[](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.Hotel-Information)

Dover

9.2/10

Wonderful

(22 reviews)

"Highly recommend clean beautiful stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Douglas D.

CA $84

CA $431 total

includes taxes & fees

Mar 31 - Apr 1

[](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-Den.h36778065.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/455aec2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/146a8911.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/77b10ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player](https://images.trvl-media.com/lodging/73000000/72140000/72131900/72131894/2828ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information)

Clock Tower Base Area

9.2/10

Wonderful

(28 reviews)

"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David A.

CA $96

CA $344 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Ludlow-Hotels-Ski-InOut-Condo-With-Patio.h72131894.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w2000h1332x0y1-7eab51dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/dd5b1f55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1996h1332x1y1-302f86ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72603600/72603570/w1999h1332x1y1-792770fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two Double bed Hotel Room with outdoor heated pool 216

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.Hotel-Information)

Killington

CA $172

CA $250 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/Bridgewater-Corners-Hotels-Two-Double-Bed-Hotel-Room-With-Outdoor-Heated-Pool-216.h72603570.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w2000h1332x0y1-debdc5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/5f7ca819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-5c4dd77d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![WiFi](https://images.trvl-media.com/lodging/39000000/38200000/38197000/38196993/w1999h1332x1y1-dd061e19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Two Double Bed Standard Hotel Room with outdoor heated pool 101

[](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information)

Killington

8.2/10

Very good

(17 reviews)

"Loved this lodging. Super fun outdoorsy place. Enjoyed the warm pool and grills and picnic table area. Liked the coffee in mornings in the office. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dr Arun

CA $172

CA $250 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/Killington-Hotels-Two-Double-Bed-Standard-Hotel-Room-With-Outdoor-Heated-Pool-101.h38196993.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/c7719d69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/6fb4f927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/8238a1ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33550000/33549300/33549240/4f15cc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Walpole-Hotels-Your-Own-Private-Farmhouse-On-Spectacular-Farm.h33549240.Hotel-Information)

Walpole

10/10

Exceptional

(38 reviews)

"Lovely place would definitely book again"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sean M.

CA $334

CA $412 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Walpole-Hotels-Your-Own-Private-Farmhouse-On-Spectacular-Farm.h33549240.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/bd9e5999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Towels](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/a8fc6b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/a9f17f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74110000/74100200/74100124/b6513e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Studio Condo with Great Location, WiFi & Kitchenette

[](https://www.expedia.ca/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.Hotel-Information)

Ludlow

8.8/10

Excellent

(31 reviews)

"Great location and great place!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Linda G.

CA $143

CA $318 total

includes taxes & fees

Mar 18 - Mar 19

[](https://www.expedia.ca/Ludlow-Hotels-Cozy-Studio-Condo-With-Great-Location.h74100124.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2026-03-25&endDate=2026-03-26&regionId=89014&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_89014)

## Top Chester Hotel Reviews

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187_y.jpg)

### The Equinox Golf Resort & Spa

6/10 Okay

"Hot tub nor sauna we’re working. This is pretty important for a ski Hotel, or anyone that bills themselves as a spa. "

[](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information)

![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/06298210_y.jpg)

### Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Very clean, spacious rooms, very apartment like. Everything we needed to have a great girls weekend the pool was enormous and very warm beautiful grounds. The kitchen had everything we needed to cook meals. The staff was wonderful during check-in. The room had everything we needed. Didn’t need to call them again."

[](https://expedia.ca/Brownsville-Hotels-Holiday-Inn-Club-Vacations-Mount-Ascutney-Resort.h425171.Hotel-Information)

![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg)

### Pointe at Castle Hill Resort

8/10 Good

"Yes"

[](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information)

![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg)

### The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Great location, most convenient hotel , everything is perfect. "

[](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information)

![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/8d6bfa64_y.jpg)

### On The River Inn

10/10 Excellent

"The breakfast and staff were AMAZING! Freshly made scrambled eggs, bacon, sausage patties, french toast, waffles, Cabot yogurt with all the fixings, dry cereal, hot oatmeal, breads, muffins, danish, etc. Everything was delicious and well presented as well! Forgot to mention freshly gound coffee! YUM! KUDOS!"

[](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information)

![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg)

### The Manchester View

10/10 Excellent

"This place worked out wonderfully. Clean, comfortable and a great value. Location around 5 min to downtown Manchester. 20 minnto Stratton. Highly recommend "

[](https://expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.Hotel-Information)

![Kimpton Taconic Hotel by IHG](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572989/21acdcb9_y.jpg)

### Kimpton Taconic Hotel by IHG

10/10 Excellent

"Hotel was lovely. Beautifully appointed. Staff was excellent and very helpful. "

[](https://expedia.ca/Bennington-Hotels-Kimpton-Taconic-Hotel.h1572989.Hotel-Information)

## Frequently asked questions

### Searching for romantic hotels in Chester?

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

### When is the best time of year for a romantic getaway to Chester?

### What is there to do in Chester?

### What's the best way to get to Chester and around town during my romantic getaway?

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