A stone waterfall in a forested area with a stone wall in the background.

Book Chester Bed & Breakfast

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    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Chester bed & breakfast

A patio with four chairs and a stone fire pit, surrounded by a well-maintained lawn and trees.

1. The Neighbour House B&B

The Neighbour House B&B
3.5 star property
Long Valley
9.0 out of 10, Wonderful, (427 reviews)
"Such a beautiful property! Iris and Rafi were so nice and welcoming! We will be going back the first chance we get!"
United States
Paul
$147 nightly
The price is $164
Oct 19 - Oct 20
Total with taxes and fees
The Neighbour House B&B
A room with a fireplace, a table with a vase of flowers, and a chandelier.

2. Whistling Swan Inn

Whistling Swan Inn
3.0 star property
Stanhope
8.8 out of 10, Excellent, (578 reviews)
"breakfast was very yummy and audrey is a very kind, thoughtful, and organized innkeeper. Would definitely stay again!!"
United States
Hannah
$183 nightly
The price is $205
Oct 4 - Oct 5
Total with taxes and fees
Whistling Swan Inn
A garden setting with three wooden chairs, a large tree, and a white tent in the background.

3. Inn at Millrace Pond

Inn at Millrace Pond
3.0 star property
Blairstown
8.6 out of 10, Excellent, (87 reviews)
"The staff is very friendly and helpful. Beautiful property."
United States
Wei
$220 nightly
The price is $252
Oct 7 - Oct 8
Total with taxes and fees
Inn at Millrace Pond
A spacious living room with a large, ornate rug, leather sofas, and a dining area in the background.

4. The Inn at Peacfield Farms

The Inn at Peacfield Farms
Alexandria
10.0 out of 10, Exceptional, (4 reviews)
"We had a great stay."
United States
Michael
$278 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Peacfield Farms
A spacious living room with a large, ornate rug, leather sofas, and a dining area in the background.

5. The Inn at Peacefield Farms

The Inn at Peacefield Farms
Alexandria
10.0 out of 10, Exceptional, (1 review)
"What a great place this is. Peaceful, quiet, great walking the property, watching the horses..Just a great place overall.Stacey & the rest of her staff were very welcoming and helpful if needed.."
United States
Scott W.
$278 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Peacefield Farms
A spacious living room with a large, ornate rug, leather sofas, and a dining area in the background.

6. The Inn at Peacfield Farms

The Inn at Peacfield Farms
Alexandria
$278 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Peacfield Farms
A spacious living room with a large, ornate rug, leather sofas, and a dining area in the background.

7. The Inn at Peacfield Farms

The Inn at Peacfield Farms
Alexandria
$278 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Peacfield Farms
A spacious living room with a large, ornate rug, leather sofas, and a dining area in the background.

8. The Inn at Peacfield Farms

The Inn at Peacfield Farms
Alexandria
$278 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Peacfield Farms
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

Madison Hotel

Madison Hotel

10/10 Excellent
"The Madison Hotel is easily one of the finest and most enjoyable hotel experiences I have ever had—and I have stayed in many hotels. From the moment I arrived, the staff demonstrated a level of genuine warmth, professionalism and hospitality that is increasingly difficult to find. The property itself is breathtaking. Its beautiful Georgian-style architecture, traditional interiors and extraordinary glass Conservatory give the Madison the gracious character of another era while remaining wonderfully comfortable and inviting. Rod’s Steak & Seafood Grille is equally special: gorgeous wood paneling, leather seating and the warmth of a classic American steakhouse, complemented by terrific service, excellent food and surprisingly reasonable prices. Even the complimentary breakfast is exceptional—they mean a full, beautifully prepared breakfast with an actual assortment of quality food. Room service was prompt, consistently delicious and another example of something the Madison simply does better: whatever you order seems to arrive as the premium version of it. For travelers visiting the area or heading into New York, Convent Station and the Morris & Essex Line are directly across the parking lot. I also saw the care given to the hotel’s wedding events, and the setting is magnificent. Beautiful property, wonderful food and truly outstanding people. The Madison understands hospitality. I cannot recommend it highly enough."
Phillip Denton 4-night trip
Posted 2 hours ago
Madison Hotel

Find out more about Chester

Chester B&B information

Number of reviews
92
Accommodation
10 B&B
Lowest Price
$164
Highest Price
$293

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from $164 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 peak season, which runs from July to September. This vibrant period draws travelers eager to explore the stunning natural beauty of the region, with its lush landscapes and crystal-clear lakes. With warm temperatures ranging from the mid-70s to low 80s Fahrenheit, outdoor enthusiasts can enjoy a variety of activities such as hiking, boating, and fishing, all while soaking in the breathtaking scenery that Chester has to offer.

September, in particular, is a fantastic choice for those who appreciate a more tranquil experience. While still enjoying pleasant weather, visitors can witness the changing colors of the leaves, offering a picturesque backdrop for any outdoor adventure. The crowds begin to thin out, allowing for a more relaxed pace while exploring Chester's charming local shops and eateries.

For travelers looking for a more budget-friendly option, December presents an opportunity to enjoy the winter wonderland of Chester. This time of year invites cozy indoor activities, like unwinding by the fire in your B&B, while the surrounding snow-covered landscape creates a peaceful atmosphere.
What is the difference between a Chester Bed and Breakfast 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.

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