Explore top 2025 4 Star Hotels in Winchester

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Top Winchester 4 Star hotels

Inn on Putney Road

192 Putney Road, Brattleboro, VT

$267 nightly

$294 total

Nov 2 - Nov 3

Total with taxes and fees

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free self parking, and free train station pick-up. Traveling on business? ...

9.8/10 Exceptional! (55 reviews)

"Inn was fantastic and owner/staff were also incredible"

Reviewed on Oct 3, 2025

Chesterfield Inn

20 Cross Roadd West, West Chesterfield, NH

$301 nightly

$327 total

Nov 2 - Nov 3

Total with taxes and fees

A restaurant and a bar/lounge are featured at this bed & breakfast. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, ...

9.6/10 Exceptional! (30 reviews)

"This is a genuine five star property, an ideal of what a country inn should be. Beautifully designed and decorated, comfortable and welcoming, charming staff. One of the nicest places we’ve ever stayed."

Reviewed on Jun 18, 2025

The Brattleboro

770 South St, Brattleboro, VT

This bed & breakfast features a seasonal outdoor pool and a hot tub. Enjoy the sauna and free perks like cooked-to-order breakfast and free self parking. A bar/lounge, ...

"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return."

Reviewed on Aug 14, 2023

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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.

4 Star Hotels Winchester

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Winchester 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Winchester will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Winchester, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.