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Our top choices for Winchester 4-star hotels
1. Four Columns Inn
Four Columns Inn4.0 star property
Newfane
9.8 out of 10, Exceptional, (63 reviews)
9.8/10
Exceptional
(63 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
Raymond
The price is AED 558
AED 558
AED 608 total
includes taxes & fees
23 Nov - 24 Nov
2. Inn on Putney Road
Inn on Putney Road4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
9.8/10
Exceptional
(61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
"Helpful staff, wonderful breakfast and homey ambiance."Karla
The price is AED 980
AED 980
AED 1,078 total
includes taxes & fees
15 Nov - 16 Nov
3. Chesterfield Inn
Chesterfield Inn4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
9.4/10
Exceptional
(106 reviews)
"Great stay"
"Great stay"Wayne
The price is AED 1,106
AED 1,106
AED 1,200 total
includes taxes & fees
15 Nov - 16 Nov
4. Updated Vintage Apartment < 1/2 Mi to Main St
Updated Vintage Apartment < 1/2 Mi to Main St4.0 star property
Keene
5. The Brattleboro
The Brattleboro4.0 star property
Brattleboro
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return.
"
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return.
"Roger
Top Winchester Hotel Reviews
Inn on Putney Road
Inn on Putney RoadBrattleboro
10/10 Excellent
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Superlative. Beautiful house and grounds with access to woodland trails and the river. Super friendly host and staff. Excellent breakfast. Best quality beds, linens and amenities.
Victoria
Chesterfield Inn
Chesterfield InnWest Chesterfield
10/10 Excellent
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.
Beverly
Four Columns Inn
Four Columns InnNewfane
10/10 Excellent
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
It was a short stay but an awesome one. Newfane is a quaint area. The room itself was beautiful. It was nice and quiet; didn’t hear others. Very clean. Would loved to have stayed longer. A little pricey but then it again it was a last minute booking and also peak foliage season.
Nettie
Frequently Asked Questions
How much does it cost to stay in a 4-star hotel in Winchester?
To lock in a 4-star hotel in Winchester that matches your budget, take advantage of Expedia's handy search filters. Browse the availability during your chosen dates and use our pricing filter to set your maximum rate. You can also list your results by the most economical escape first.
- Search for the lowest price from AED 557
What's the difference between 5-star and 4-star hotels in Winchester?
Offering an inviting traveler experience and upmarket surroundings, 4-star hotels are a wonderful option for your Winchester trip. These types of accommodations generally feature loads of handy amenities that make it easy to unpack and unwind — think complimentary bathrobes, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to indulge you in high-end perks and amenities. 24-hour front desk, premium toiletries and world-class dining are typically featured at these swanky retreats.
Does Winchester have any 4-star all-inclusive resorts?
Finding your dream hotel in Winchester is as simple as entering your dates and destination, and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, food and activities, or choose a standard 4-star resort in or around this sought-after destination.