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Old Waterstreet Inn

Winchester, VA 22601 USA (Show map)
28 Reviews
$140 - $160
per night

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Old Watersrteet Inn is a grand old home located in Winchester's historic district, within easy walking of Old Town shops, restaurants, galleries, and nightlife. The federal style house was built in 1840-1890. Architectural details enhance the elegance of the inn, and your hosts have furnished it in an eclectic mix of styles, of old and new, which creates a charming, casual ambience. Our rates include a full breakfast, and 24-hour soft drinks, tea, and light snacks. Guests can relax in our living room with fireplace, in our sunroom, or on the terrace garden and yard. Each of the 5 rooms has its own distinct character. All rooms have private baths, queen beds, comfortable seating, central air, and wireless internet access. Featured in Washingtonian magazine Feb. 2008, recommended by Frommers, Top ratings on Tripadvisor



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  • Guest room4.5
  • Service4.8
  • Value4.6
  • Cleanliness4.8
  • Dining4.6

Score Breakdown based on
28 Reviews

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Wonderful Stay

4.6 on December 18, 2013

The Innkeepers were both friendly & welcomed us to their home. Food was fabulous and service very good. Enjoyed the company of the other quests!


4.8 on August 21, 2013

A totally lovely Inn. The room was beautiful and the bed was very comfortable. Jeannie was wonderful and gave us great insight into the area. Her recommendations for sights and foods were spot on. Her breakfasts were out of this world!

Location, Location, Location

4.6 on August 15, 2013

Location A+ in historical district close to restaurants and historic neighbourhoods. Beautiful B&B,wonderful breakfast and Innkeeper, great personality. Loved the area and friendly atmosphere. Great stay.

Our stay in Winchester

5 on August 14, 2013

Our stay at the Old Waterstreet Inn was superb! The hostess was so accommodating and friendly. The room and the breakfast was lovely. We were very pleased with all aspects!

A wonderful stay

5 on August 12, 2013

A beautiful, stately home built in the mid 1800's; wonderfully appointed and decorated by Jeannie. Close to old town. Jeannie's hospitality and attention were beyond compare. We love this B&B!!

Warm and Inviting

4.2 on August 09, 2013

A beautiful B&B with a gracious Inn Keeper.. Felt right at home the minute I walked in.. Absolutely delicious breakfast, very surprised at spaciousness of rooms. Just lovely.

Terrific Vacation

4.6 on August 07, 2013

A house with history and décor to match, but with 21st century conveniences; genial, generous, and helpful hosts; tasty and bountiful breakfasts. Location can't be beat.

Old Waterstreet Inn Winchester, Va

5 on July 09, 2013

Delightful stay, great service. This was probably the cleanest B&B ever!! Thanks so much!

A real gem

4.4 on April 19, 2012

My husband and I stayed at the Old Waterstreet Inn for just one April evening on our travels from the south to the north. After many hours of road wearniness, we arrived at this Inn and breathed a sigh of relief. It was all we'd hoped for and more. Innkeepers Jeannie and Mark were so helpful in getting us settled and recommending a place close by for late night dinner that was just what we needed. We felt very much at home in this amazing home of wonderful architecture, history and eclectic but tasteful decor. If we pass this way again, this Inn is a "must stay" on our list.

Second time at the inn

5 on April 18, 2012

After my first stay at Jeanne and Erik's inn back in 2010, I knew this was the place to plan a girlfriends' getaway weekend. This finally happened last weekend. We all loved our stay there and plan to come back again.

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Location Type

in historc district, Downtown, Small town


Washington DC, DC (IAD-Dulles) 50 miles

Area Attractions

Antique Shopping, Art Galleries, Gourmet/Fine Dining, Historical interests, Live Music, Movie Theater, Museum, National/State parks, Nature area, River, Winery

Inn Details

Establishment type

Bed and Breakfast, Historic Inn

On-site amenities

Library , fresh flowers and bedside chocolates

Room amenities

Air conditioning, Alarm clock, Fireplace

On-site activities

Golfing, Hiking trails, Horseback riding, Museum of the Shenandoah Valley, theatre and concerts, 5 public golf courses, civil war battlefields and sites, hiking/fishing nearby, Old Town shops, restaurants, galleries, Shopping

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  • Check In:: 3:00-6:30
  • Check Out:: 11:00
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Suitable For Children: children over 12
  • Guest Pets Allowed: No

Terms and Conditions

  • Minimum Stay: only holiday weekends, october weekends, and Winesap room on winter months weeke
  • Deposit Amount Required: credit card required to book, for cancellation purposes
  • Cancellations: Cancellations for 1 night stays made 8 days or more before will receive a full refund. Cancellations for multi-night stays, multi room bookings, holidays, and event weekends is 14 days out. If you cancel in less than the specified time, you will be charged the full amount for the room, unless it is rebooked. Changes are treated the same as cancellations.



Jeanne Faith and Erik Erdal

Languages spoken

Norwegian, English

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  • Time Served: 8:30-10:00
  • Serving Location: Dining Room

Signature Dish

Almond amaretto french toast
Thick french toast flavored with amaretto and orange juice and crusted with sliced almonds.



Special Package

3 Night Discount

Stay 3 nights and get 15% off the 3rd night (and additional nights). cannot be combined with other offers

Contact Innkeeper

Details Diamond Collection

217 West Boscawen Street , Winchester, VA 22601 USA (Show map)

Property highlights

Free $60 gift card with a $300+ purchase