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Incredible Family Reunion Place! Executive Home w/Indoor Pool, Hot Tub AND MORE!

27 Reviews
Bedrooms 11
Property type house
Minimum Stay 2 nights

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Minimum Stay
2 nights


Photos and Description of this 11 bedroom holiday home in Winchester - Winchester Guest House

11 Separate Sleeping Rooms/Areas, Theater & Billiard Room, Pool, Spa, 6 Acres



Beautiful, executive home with 3 levels, living room, conference/large dining room (seats 24) room, small dining room (seats 6-8), theater/billiard room, huge indoor swimming pool and hot tub, 9 private sleeping rooms + 2 common sleeping areas (11 sleeping rooms total) and 7 bathrooms. Beds/sofa beds to sleep 36 people. Extra portable bedding for a total of up 44 people for larger family reunions and certain group situations - contact owner for details. Exceptional for family reunions and retreats.

We are situated on nearly six park-like acres.

Features include:

Indoor Pool

Hot Tub

Theater Area with 10' screen

Billiard Room

Conference Room with huge conference table that seats 20

Table Shuffleboard

Fireplace Suites

Large Family Suites sleeping 5 to 9 persons

High Speed Wireless Internet (complimentary)

Available Spa Services including Massage and Facials

Living Room with Leather Seating & Gas Fireplace

Formal Dining Room (seats up to 10)

Complimentary DVD Movies

Catered Meals for conference/retreat groups

We feature 6 acres of park-like grounds for strolling, relaxing, and playing. On the property you will find:



Swing for Two under the Maple Tree

Lighted Patio Area with Seating for up to 18

Field large enough for the team sport of your choice.

Within 5 minutes you will find:

Award Winning 27 Hole Golf Course

Zip Line

Rock Climbing Wall

Hiking Trails

High Bank Motor Speedway

Tennis Courts

Drive-In Movie Theater

3 Screen Cinema

Antique Shopping

Family Dining

Sports Bar


Indoor Pool normally open April to December; however, special arrangements to heat the pool for your group may be possible during the months of January, February, and March, Indoor Hot Tub Open Year Round.

More Details
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed

Ted Davenport
Member since: 2013
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
18 October, 2016
Call Owner

About Ted Davenport

Ted is a former management consultant and Director with Ernst & Young focusing on information technology related projects. Ted also worked for Price Waterhouse during his management consulting career.

Ted is a graduate of Ball State University with a B.S. is Telecommunications and a Business Administration Minor. In addition to directing activities at the Inn, Ted and daughter Kiera - an Indiana University graduate - operate Uncharted Pixels LLC - a web services, branding, and video production services company. Ted is also a private pilot.

Debbie is the chef of the team when the property is operated as a Bed and Breakfast. She prepares excellent breakfasts for our guests and manages the housekeeping functions making sure your rooms are up to her exacting standards of cleanliness and comfort. She was awarded the Hoosier Hospitality award by Indiana's Lieutenant Governor!

Debbie attended Indiana University East in Richmond and has worked in the healthcare, childcare, and social services fields during her career.

Ted Davenport purchased this house in 1999

Why Ted Davenport chose Indiana

After living near Chicago, St. Louis, San Francisco, Los Angeles, and Cincinnati, We purchased this property to get back to our Hoosier roots near the Whitewater River valley. Both Ted and Debbie were born in Richmond just 25 minutes south of the property. Winchester is a great little town brimming with family values, lots of churches, nearby shopping, and close to our family.

What makes this house unique

With six park-like acres, 3 fireplaces, and an indoor pool and spa, a conference room that seats 24, separate formal dining room that seats 8, a nice patio with seating for large groups, and nearly 6 park-like acres, this property has everything you are looking for in a family reunion or retreat destination!. This home has something for everyone!. The older folks can sit by the living room fire or on the patio and have great conversation while the kids enjoy the pool or the theater/game room. The teenagers can play volleyball and badminton on the east lawn while the guys head over to the award winning 27 hole golf course and the ladies go antique shopping. We have a game closet filled with board games and playing cards. Free WIFI is available throughout the property and most rooms have HDTVs with HDMI connections. The winery tours are not to be missed with live entertainment on some evenings. Nearby Camp Yale offers a rock climbing tower and zip line as well as a low ropes course. Fishing is available in nearby Farmland, Richmond, and Muncie. The historic Winchester Speedway "the worlds fastest half mile" is 10 minutes away offering pulse pounding high banked auto racing and Eldora Speedway (about 45 minutes) offers awesome dirt track racing in the summer. Take a day and enjoy the Antique Alley trails for great shopping and don't forget to stop by Silvertowne for a unique gift shopping experience in Winchester. But you may never want to leave the property. This is truly a great family home with all we have to offer on the premises! Perfect for reunions and large family gatherings. Check out our ratings by our valued guests!


based on 27 holidaymaker reviews

Incredible Family Reunion Place! Executive Home w/Indoor Pool, Hot Tub AND MORE!
average rating of 4.740741 based on 27 reviews

Family Weekend

  • 5 of 5

The visit was planned by my Mother sadly she passed before the visit but we knew she would want us on go and so we did whathe a great place to get your family together at we had a blast thank you Ted Davenport for providing a great place for everybody to gather

  • Review Submitted: Sep 5, 2016
  • Date of Stay: Sep 2016
  • Source: VRBO, from HomeAway
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Spacious home with amenities for large groups

  • 4 of 5

Ted and his wife were wonderful to work with, very reliable and returned any request in a timely manner. Our group of 14 had more than enough room with private bedrooms and baths for each of the 7 couples. We loved the indoor pool, theater room with over 100 DVDs, back patio and huge yard for lawn games and seating for outdoor conversations, and the huge indoor dining table for all of us and then some. A Minor electrical problem and a gas grill that didn't heat were the only weekend drawbacks, but all had a wonderful time at this unique and well appointed property.

  • Review Submitted: Aug 28, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
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Very nice!

  • 5 of 5

Great hosts! The owners went out of their way to accommodate my family and our needs. The home isn't fancy, but it's warm and inviting and clean. A little pricey given the location, but overall good experience. 😊

  • Review Submitted: Aug 18, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
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Great property!

  • 5 of 5

We had a wonderful time staying in this spacious home. We lived the amenities and the indoor pool as it rained most of our stay. Thanks for a wonderful time. Ted was wonderful to work with and made sure we had what we needed. Great time!

  • Review Submitted: Aug 14, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: It is great to know that, despite the rain, these guests still had a great time! Our indoor pool, theater/game room with billiards, darts, table shuffleboard and more, large living room and huge conference room, huge complimentary DVD collection, closet full of board games and several tables to play them, and high speed WIFI help make an indoor experience at the Winchester Guest House Reunion House a great time regardless of the weather!
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Summer Getaway 2016

  • 5 of 5

We spent the weekend of July 4th at this awesome house! With a party of 37 including kids, it was just the right size to accommodate all of us comfortably.

Some of the highlights of the property were proper beds for all of us, enough bathrooms so that no one had to wait in line, the outdoor grounds were perfect for games like soccer, badminton, cricket and volleyball. The conference/dining room with the incredibly large size table was excellent for the mealtimes and watching Euro cup soccer together! The pool was one of the main attractions for the kids, who used it extensively. It being indoors, they could jump in at any time of the day and also when it was raining outside. Plenty of towels and linens were provided. Only one drawback, which I had already mentioned to Ted was that considering the size of the house and the large number of heads it could accommodate, a regular size cook top would be very convenient. We did use the griddle but it would not hold large pots for so many and didn't get that much heated to get anything to boil and cook fast. We did manage with the double oven. but a regular stove would make it just perfect. The nearby Walmart was very convenient.

Overall, we were very satisfied with the property and will definitely go back next year.

  • Review Submitted: Jul 30, 2016
  • Date of Stay: Jun 2016
  • Source: VRBO, from HomeAway
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Wonderful atmosphere

  • 4 of 5

Just finished a family reunion in Winchester. Wonderful, homey environment - I counted 9 kids in the pool within the first hour we arrived. House has all the basics (sheets, towels, soap, pots, pans, etc.) and plenty of them. 6 acres of space, with volleyball and badminton nets. We provided our own cornhole, soccer, and wiffle ball stuff, plus kites! Review would be 5 stars except for the hot tub - jets were feeble, making it more like a bathtub - and a few issues with the basement rec room items. Owner said he would fix the rec room issues.

We had a total of 37 people for the weekend. The house was fully capable of handling this many people comfortably although not all of the adult couples had private rooms. Kids had a blast, adults had a great time. It is definitely a location where you make your own fun.

  • Review Submitted: Jul 23, 2016
  • Date of Stay: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: Large family groups are a mainstay for us at the Winchester Guest House Reunion House! The rec room items specified as needing attention by this guest were 1. not enough pool cues (and 1 was broken) and 2. the powder wax for the shuffleboard table was missing. We bought several new pool cues and a new can of wax powder so great fun is to be had by all in the rec room (we call it the theater/game room). There is also a set of putters and putting cups that can be moved around to create your own mini golf course in that room. As far as the jets in the hot tub are concerned, it is designed not to move air to avoid excessive hot moisture permeating the pool room. The tub is primarily designed for relaxing and conversation. We are looking into an outdoor hot tub with more invigorating jets. Stay tuned! We hope to see this family again soon and look forward to serving your family!
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Nearest Airport
63 Miles
Dayton, OH
Nearest Barpub
1.5 Miles
A&B Cafe
Nearest Golf
0.5 Miles
Winchester Golf Club
Nearest Train
47 Miles
Connersville, IN
Nearest Motorway
0.5 Miles
US 27
Nearest Restaurant
1 Miles
Randolph Grill
Nearest Ski
87 Miles
Mad River Mountain
Nearest Beach
22 Miles
Prarie Creek and New Paris, OH
Car: necessary

Winchester is a quaint town of just under 5000 people with a beautifully restored courthouse square with shopping and a 3 screen theatre. Within 30 minutes you can see Broadway shows, enjoy two symphony orchestras, ride a zip line, see an Egyptian mummy, golf on several beautiful golf courses, visit a beautiful cultural center and gardens, visit several excellent museums, go antiques shopping on two antique alley trails, go lake fishing, clear water snorkeling/scuba diving, snow tubing, and much more!


Prices & Availability

Prices for this holiday house in Winchester, Indiana

Rental Basis:
per property
Owner accepts payment in:
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Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
My Standard Rate
2 night minimum stay
for 2 nights
Notes: Rates are based on 10 guests; add £9 per night, per additional guest

Additional pricing information

Cleaning Fee £164
Property Damage Protection £81
Tax Rate 12.0%

Rates are subject to change until the reservation is confirmed and initial payment has been made. Renter must agree to the terms of the rental agreement. Renter must put an accurate estimate of the total number of persons age 2 and older who will be occupying the property in order to accurately calculate the total rental amount.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
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Available arrival


Accommodation and facilities for this holiday house in Winchester, USA

Property Type:
  • house
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Optional
Floor Area:
  • 6500 sq. ft.
Location Type:
  • rural ...
  • Away From It All
  • Family
  • Sports & Activities
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven ...
  • Refrigerator ...
  • Hob ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 16 people
  • 7 Bathrooms
  • Master Suite Bath - Toilet , Bath with Shower , Double Bowl Sink
    Road Warrior Bath - Toilet , Shower Enclosure , 48' Shower with built-in seat
    Parents Room Bath - Toilet , Shower Enclosure
    Chateau Suite Bath - Toilet , Bath with Shower , Sunken very deep bathtub w handheld shower, double bowl sink
    Fireplace Suite Bath - Bathroom can be accessed from 2 rooms
    Library Bath (#6) - Toilet , Shower Enclosure , Double Bowl Sink Black Kohler Fixtures
    Owners Suite Bath (#7) - Toilet , Shower Enclosure
  • Most bedrooms have en-suite private baths. (Rooms 5A and 5B use the bathroom for #5, 7A and 7b uses the bathroom for 7 (2 bedroom apartment).
  • 11 Bedrooms, Sleeps 44
  • Master Suite (#1) - 1 Extra Lg. Double Bed , 1 Sofa bed/Futon , Queen is a fold-out sofabed, Full bath. Sleeps 4
    Parents Room (#3) - 1 Extra Lg. Double Bed , King bed, Private Bath with Shower/ Sleeps 2
    Road Warrior (#2) - 1 Large Double Bed , This is our smallest bedroom with ensuite bath. Sleeps 2
    Fireplace Suite Dorm Room (#5A) - 1 Bunk Bed , Adjacent to Theatre/Game Room Sleeps 3 (Twin over Full Bunk)
    Chateau Suite (#4) - En-suite bath with sunken oversize tub, fireplace, Sleeps 5
    Fireplace Suite (#5) - 1 Extra Lg. Double Bed , With fireplace, adjacent to the Theater/Game Room Sleeps 2
    Library (#6) - 1 Large Double Bed , Private Bath with shower and double bowl sink. Sleeps 2
    Executive Suite (#7) - 1 Extra Lg. Double Bed , King in Private Bedroom, Sleeps 2
    Fireplace Suite Theater Room Area (#5B) - 2 Single Bed , 3 Sofa bed/Futon , Great room for kids and teenagers. Sleeps 8 (1 on sectional)
    Executive Suite 2nd Bedroom (#7a) - 1 Large Double Bed , Part of the 2 Bedroom Executive Suite Sleeps 2
    Executive Suite Living Room (#7b) - 1 Sofa bed/Futon , Living room area of the Executive 2 BR Suite. Sleeps 2
  • Most bedrooms include a TV and DVD or Blu-Ray Player and en-suite private baths. Several bedrooms have flat-screen HDTVs. WIFI Available in all rooms. For large groups we have portable bedding available that can fit in several of the bedrooms.
  • Books ...
  • DVD Player ...
  • Game Room ...
  • Games ...
  • Pool Table ...
  • Satellite / Cable ...
  • Television ...
  • Toys ...
  • Video Games ...
  • Video Library ...
  • Terrace ...
  • Golf ...
  • Garden ...
  • Barbecue ...
  • Tennis ...
  • Minimum Age Limit for Renters ...
  • children welcome
  • non smoking only
  • pets not allowed
Pool / Spa:
  • Heated Pool
  • Hot Tub ...
  • Indoor Pool
  • Private Pool ...
Onsite Services:
  • Concierge
  • Massage
  • Staff
  • arboretum
  • botanical garden
  • churches
  • cinemas
  • festivals
  • Health/Beauty Spa
  • library
  • live theatre
  • museums
  • playground
  • recreation centre
  • restaurants
  • water parks
  • winery tours
Leisure Activities:
  • antique hunting
  • bird watching
  • Boating
  • Horseshoes
  • photography
  • scenic drives
  • Shopping
  • Shuffleboard
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • hospital
  • laundrette - serviced
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • Basketball Court
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • Kayaking
  • rafting
  • Rock Climbing
  • sailing
  • diving
  • snorkelling
  • Snorkeling/Diving
  • Snowmobiling
  • swimming
  • tennis
This property is advertised here (VRBO.com and Homeaway.com) as a Vacation Rental property. Breakfast is NOT INCLUDED under the pricing of this plan. Property can also be booked as a Bed and Breakfast with catered meals. Owners live in a private suite on the property.

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Portable wifi hotspot

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