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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Chester

Cromwell Manor Inn
Exterior

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (67)
"Very gracious innkeepers; great breakfast in a beautiful setting."
$241 nightly
The price is $284
Aug 24 - Aug 25
Total includes taxes and fees
Cromwell Manor Inn
Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (124)
"We loved our stay here! It was cozy, quiet, and the breakfast was amazing. The staff was wonderful at getting accomodations ready for our child before we arrived. Highly recommend for anyone who wants to enjoy a quiet and relaxing getaway within walking distance to shops and restaurants."
$190 nightly
The price is $215
Sep 5 - Sep 6
Total includes taxes and fees
Borland House Inn
Alpine Haus Bed & Breakfast Inn
Terrace/patio

Alpine Haus Bed & Breakfast Inn

3.0 star property
9.2 out of 10, Wonderful, (313)
"The porch outside our room was a great spot to sit and enjoy the beautiful view of the valley and surrounding hills at sunset."
$200 nightly
The price is $229
Aug 6 - Aug 7
Total includes taxes and fees
Alpine Haus Bed & Breakfast Inn
Villa Verde BB Greenwood Lake NY
Exterior

Villa Verde BB Greenwood Lake NY

4.0 star property
10.0 out of 10, Exceptional, (7)
"Eva was a gracious host. The breakfast was very good. "
$225 nightly
The price is $255
Aug 11 - Aug 12
Total includes taxes and fees
Villa Verde BB Greenwood Lake NY
Tin Brook Bed & Breakfast
Exterior

Tin Brook Bed & Breakfast

3.0 star property
9.4 out of 10, Exceptional, (115)
"Very nice accommodations & staff."
$138 nightly
The price is $156
Aug 6 - Aug 7
Total includes taxes and fees
Tin Brook Bed & Breakfast
Buck's Homestead B&B
Front of property

Buck's Homestead B&B

2.5 star property
9.6 out of 10, Exceptional, (58)
"Very comfortable stay"
Buck's Homestead B&B
The Castle at Skylands Manor
Property grounds

The Castle at Skylands Manor

3.5 star property
7.4 out of 10, Good, (389)
"Pretty area"
$199 nightly
The price is $222
Aug 6 - Aug 7
Total includes taxes and fees
The Castle at Skylands Manor
The Dominion House Bed & Breakfast
Superior Double Room, Ensuite (Primrose) | Miscellaneous

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (227)
"Amazing hospitality,"
$215 nightly
The price is $243
Aug 11 - Aug 12
Total includes taxes and fees
The Dominion House Bed & Breakfast
Stagecoach Inn
Restaurant

Stagecoach Inn

3.5 star property
9.6 out of 10, Exceptional, (76)
"Staff was amazing friendly attentive always smiling. Food and drinks were delicious. Loved the ambience of the room. "
$209 nightly
The price is $257
Aug 6 - Aug 7
Total includes taxes and fees
Stagecoach Inn
Columbus Hotel
Economy Studio | 1 bedroom, individually decorated, individually furnished, desk

Columbus Hotel

3.0 star property
6.0 out of 10, (6)
"21 minutes ago on Google It's a family owned and operated hotel. Norman was kind, communicative and thorough. Keyless entry made checking in super easy. We had a business suite, which is basically a studio apartment. Kitchen , bathroom, bed/living space was clean and neat having a really nice modern clean aesthetic. There was even a candle left for us to enjoy. Overall was a very pleasant stay! Very grateful. "
Columbus Hotel
Caldwell House Bed & Breakfast
Room | 1 bedroom, premium bedding, pillowtop beds, individually decorated

Caldwell House Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (473)
"Great place to stay. Wonderful breakfasts. Gracious and warm hospitality."
Caldwell House Bed & Breakfast
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"We had a great stay here. The manager was the best (Corlina? Corvina?) Everything was clean and the room was super comfortable. And the breakfast was off the charts! Waffles, eggs, delicious pastries, French toast…. Best breakfast I’ve had at a hotel that was included with the room! The only negative was the pool area was overcrowded, loud and full of kids who couldn’t have been potty trained but weren’t in swim diapers…"
Oveta 1-night trip
Posted 21 hours ago
Sleep Inn & Suites Middletown - Goshen

Frequently asked questions

What are the most popular Chester Bed & Breakfasts?
The Dominion House Bed & Breakfast stands out as an exceptional choice for travelers seeking a cozy retreat in Chester, NY, boasting an impressive 9.6 rating. Guests rave about the delightful breakfast and the warm atmosphere, making it an ideal spot for couples looking to escape the hustle and bustle. The property features well-appointed kitchenettes in the rooms, complete with refrigerators and coffee makers, allowing for a comfortable and convenient stay.
What is the nightly rate for a B&B in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from $156 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chester?
The best time to book a B&B in Chester is during the summer months, particularly from July to September, when the area comes alive with outdoor activities and family-friendly events. This period is superb for travelers who appreciate warm weather and vibrant community gatherings, making it an ideal backdrop for sightseeing and enjoying the natural beauty of Lake Almanor.

July stands out as the peak month, attracting visitors eager to engage in water sports, hiking, and exploring the picturesque landscape. Temperatures typically range from the mid-70s to low 90s Fahrenheit, providing superb conditions for outdoor adventures. Whether you're picnicking by the lake or taking a scenic hike in the Lassen National Forest, you'll find plenty of opportunities for relaxation and recreation.

For those looking for a more budget-friendly option, October is a wonderful time to visit Chester. With the summer crowds dissipating, you can enjoy the stunning fall foliage that blankets the region in vibrant colors, all while experiencing a more tranquil atmosphere. This is also a great time for cozy fireside evenings at your B&B, adding a touch of warmth to your stay.
What is the difference between a Chester B&B and a hotel?
Every Chester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.