See all properties
Entire home

Litchfield County Four Season Country Paradise

Photo gallery for Litchfield County Four Season Country Paradise

Front entrance with gate for privacy
Aerial view of the four acre property
Exterior
Awesome house for the holidays
Tesla 220V EV charger

Reviews

9.4 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 12

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Explore the area

View map
Roxbury, CT
  • Place, Glebe House Museum and The Gertrude Jekyll Garden
    ‪8 min drive‬
  • Place, Hollow Park
    ‪8 min drive‬
  • Place, Pilgrim Mall Shopping Center
    ‪9 min drive‬
  • Airport, Danbury, CT (DXR-Danbury Municipal)
    ‪41 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4 with Acorn stair lift

1 King Bed

Bedroom 5

4 Single Beds

Living Room 1

1 Double Sofa Bed

4 bathrooms, 1 half bathroom

Bathroom 1

+2
Bathtub or shower · Bathtub · Bidet · Toilet · Shower only · Jetted bathtub

Bathroom 2

+1
Bathtub or shower · Bathtub · Bidet · Toilet · Jetted bathtub

Bathroom 3

Bidet · Toilet · Shower only

Bathroom 4

+1
Bathtub · Bidet · Toilet · Shower only · Jetted bathtub

Bathroom Downstairs

Bidet · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Garden
Dining area

About this property

Litchfield County Four Season Country Paradise

3,800 Square foot beautifully furnished gated home with 220v Tesla Charger, large outdoor deck, chaise lounges for sixteen, gorgeous western views and sunsets, art work and plants, heated 18' x 36' pool, all season outdoor Jacuzzi, indoor sauna, two indoor jacuzzis, steam shower, movie room with reclining chairs, fire place & two pellet stoves, and 86” 4K LCD & Sonos surround sound system ( including HBO Max, Netflix, Amazon Prime, Disney, Apple, Hulu, etc.), eight channel Sonos system throughout home and brand new Game Room with 9' antique pool table, foosball table, Joola ping pong table and Yoga/workout area. Kitchen has a brand new eight burner stove with two large ovens plus a large microwave, hot air/oven unit as well. You have the entire property for you and your guest during your stay! Very private four bedrooms (two king and two queens), each w/private full bath & bidet and beautiful guest half bath, attic kids room off of one of the Queen rooms with four twin mattresses and separate aircon/heating unit and living room couch that comfortably sleeps on with 1/2 next to it. Handicap Accessible. Brand new living room set . Incredibly equipped large kitchen with long eating island, breakfast nook for six, two separate outdoor eating areas and antique formal dining room for twelve.

Spectacular grounds with many large trees, views, flower beds and berry picking in late summer and early fall. Fall-heavenly foliage, hiking & biking, Winter-skiing, sitting by the fire & outdoor Jacuzzi and indoor sauna. Spring-beautiful walks & antiquing & Summer-outdoor activities, heated pool & Jacuzzi, barbecues. Brand new fire pit for ten that can be used throughout the year, large fireplace in living room and two romantic pellet stoves in movie room/lounge and game room that provide atmosphere and additional heating during the winter. Lots of firewood and two imitation green eggs with coal for grilling outside. Late night red zone includes full pool table, foosball table, stereo and lounge.

Please note that you must open fireplace flu prior to lighting and close eight hours after the fire is extinguished. Also pellet stoves must shut down via pressing the off sequence (top left button). Do not unplug pellet stoves when they are on as they will smoke! Pellet stoves require a 40 LB bag of pellets every 18 hours. Pellets are provided at no charge.

Tennis and golf nearby.

Top quality bedding, sheets, towels, toilet paper, paper toweling, spices, huge assortment of pans, woks, oils, vinegars, spices, condiments included.

Dustin Hoffman lives right down the road (2 blocks) across the street. Look for his twenty-year-old black Mercedes limo and you know he is in town.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Large Gunite Heated Pool Please see VIDEO
Best Town 1.5% NYC PoshPadsCT "SENTRY HILL", Mint 6BR, Heated Pool, Bike, BBQ
Roxbury
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
9.8 out of 10, Exceptional, (7 reviews)
Best Town 1.5% NYC PoshPadsCT "SENTRY HILL", Mint 6BR, Heated Pool, Bike, BBQ

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 12:00 PM
default

Children

Children allowed: ages 0–17
Pool next to house wo fence
default

Events

No events allowed
default

Pets

Pets allowed: dogs (limit 2 total)
Must have owner approval prior to confirmation
default

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Roxbury

Located in Roxbury, this holiday home is in a rural area. Glebe House Museum and The Gertrude Jekyll Garden and Institute for American Indian Studies Museum and Research Center are cultural highlights, and travellers looking to shop may want to visit Pilgrim Mall Shopping Center and Little Art Shop. Travelling with kids? Consider Hollister House Garden and Flanders Nature Center. Spend some time exploring the area's activities, including golfing.
View more Holiday homes in RoxburyOpens in a new window
Map
Roxbury, CT

What's nearby

  • Glebe House Museum and The Gertrude Jekyll Garden - 8 min drive - 7.4 km
  • Hollow Park - 8 min drive - 7.4 km
  • Pilgrim Mall Shopping Center - 9 min drive - 8.5 km
  • Lake Quassapaug - 12 min drive - 12.0 km
  • Quassy Amusement Park - 16 min drive - 16.2 km

Getting around

  • Appalachian Trail - 39 min drive
  • Oxford, CT (OXC-Waterbury - Oxford) - 21 min drive

Restaurants

  • ‪Minami Sushi - ‬14 min drive
  • ‪Brunch House 1850 - ‬17 min drive
  • ‪Nicks Country Kitchen - ‬20 min drive
  • ‪Al's Best Pizza - ‬10 min drive
  • ‪Constantine's Restaurant - ‬11 min drive

Frequently asked questions

Does Litchfield County Four Season Country Paradise have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Litchfield County Four Season Country Paradise?

As of 6 May 2026, prices found for a 1-night stay for 2 adults at Litchfield County Four Season Country Paradise on 13 June 2026 start from NZ$1,908, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Litchfield County Four Season Country Paradise pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Litchfield County Four Season Country Paradise?

On-site parking is available at the property.

What time is check-in at Litchfield County Four Season Country Paradise?

Check-in begins at 4:00 PM.

What time is check-out at Litchfield County Four Season Country Paradise?

Checkout is at 12:00 PM.

Where is Litchfield County Four Season Country Paradise located?

Located in a rural location, this family-friendly holiday home is within 6 mi (10 km) of Glebe House Museum and The Gertrude Jekyll Garden, Hollister House Garden, and Pilgrim Mall Shopping Center. Hollow Park and Lake Lillinonah are also within 6 miles (10 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 37 out of 51 reviews
Rating 8 - Good. 13 out of 51 reviews
Rating 6 - Okay. 0 out of 51 reviews
Rating 4 - Poor. 0 out of 51 reviews
Rating 2 - Terrible. 1 out of 51 reviews

9.2/10

Cleanliness

9.6/10

Check-in

9.4/10

Communication

10/10

Location

9.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Janet K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our family

Beautiful property with wonderful amenities.
Stayed 4 nights in Aug 2025
Verified

8/10 Good

Ray S.

Liked: Check-in, communication, location, listing accuracy
Great time for all. Hosts were great.
Stayed 5 nights in Aug 2025
Verified

10/10 Excellent

Matthew H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

As advertised, easy place to hang with friends.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

aaron l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay as always - second time here with our group! Always a pleasure! Big, clean, and well stocked!
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Laura W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as described
Stayed 6 nights in Aug 2025
Verified

10/10 Excellent

Cathy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous time with Family celebrating our daughter’s marriage!!! The house had everything you could expect and more!!! The pool and jacuzzi were beautiful. The host Brian was extremely nice and helpful. We would highly recommend.
Stayed 2 nights in Jul 2025
Verified

8/10 Good

Sandra G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely house, beautiful area

House was lovely although the fifth bedroom is not air conditioned and really only works for children. The pool and grounds were wonderful. Kitchen and other bedrooms were great. Lots to do in the area, hiking, blueberry picking , etc. The host was very accommodating and nice to deal with.
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Amy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for our family. We had two littles and 6 adults. The grounds were amazing for the kids to run around on, the game room and children’s bedroom were endlessly entertaining, and the kitchen and dining area were perfect to cook and enjoy our meals. Check-in was seamless and the owner’s tour was very helpful. The whole family loved the pool, the fire pit, the grounds, the tv room, and the game room. All areas were clean and well appointed. We also enjoyed the proximity to local playgrounds.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Waylon M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome location for our family reunion!

Great house very clean and comfortable. Perfect for hosting our family's reunion. Parts of the house are handicap friendly but still lots of big steps and transitions for some rooms that are very high for handicap. So be careful. Every one enjoyed the house and Brian took care of any questions we had.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Dani W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a completely delightful girls weekend! Brian & his wife allowed us to book only 20 or so hours in advance after our other VRBO got cancelled. We had an issue with the hot tub and they sent over a guy asap. Such a beautiful house with everything you would need!
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

James H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

This property is perfect for families. Something for everyone to enjoy and plenty of space. We absolutely loved our stay and made so many great memories!! The owners are so easy to deal with and went out of their way to make sure we had an enjoyable vacation.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Jamal P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Overall rating 5/5. I would recommend this home to other families and would stay again.
Stayed 3 nights in Aug 2024
Verified

8/10 Good

Carrie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip

Beautiful property and quiet backyard
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

serena c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun and relaxing

We stayed at a really beautiful home with gorgeous land. The host Brian and his wife were excellent and accommodate us with anything we needed. I recommend this home 100%.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

aaron l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Couldn’t be more perfect

Excellent stay. Well stocked. Great host. We had such a blast here. Family and friends - it’s perfect! Definitely coming back!
Stayed 2 nights in Jul 2024
Verified

10/10 Excellent

Sarah W.

Great Getaway Spot!

We had such a lovely stay at Brian's home! The house is gorgeous and spacious. The outdoor pool area was outstanding. We we there with two other couples as a weekend getaway from NYC and I couldn't have asked for a better place! I would choose this over the Hamptons any weekend!
Stayed 2 nights in Jun 2018
Verified

10/10 Excellent

Denyiel G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Relaxing property with many amenities

Loved the outdoor setting, with large pool, hottub, fire pit and beautiful scenery. Kitchen was well stocked, including a pantry. The bedrooms were very comfortable and nicely furnished. The owner was very responsive and helped get us settled, checked in to make sure the pool was taken care of. We had a great week.
Stayed 6 nights in Aug 2023
Verified

10/10 Excellent

Joanna J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property, great location

Great house in a great location! The house is so well-stocked, the hosts have thought of every detail. Our kids loved the pool, the hot tub, the giant TV and the basketball net. Very comfortable family home. Would definitely recommend, and definitely return.
Stayed 10 nights in Aug 2023
Verified

10/10 Excellent

Gilbert L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property. Gracious hosts!

Everything as good or better than expected. Pool great and plenty of rainy day activities as well. Kitchen very well equipped. Brian and Mariella were extremely hospitable, responsive, and pleasant to deal with! Highly recommended!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Hadiba A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Stay: Immaculate Home with Excellent Entertainment

We had a fantastic stay at this VRBO property! The home was not only clean and well-maintained, but also incredibly entertaining with its thoughtful amenities. The space was perfect for our needs, and we enjoyed every moment spent there. The owner was exceptionally easy to reach, responsive to all our inquiries and very accommodating. Their attentiveness made our stay even more enjoyable. Highly recommend this property for anyone looking for a great place to stay! We will definitely be back!
Stayed 2 nights in Aug 2024
Verified

10/10 Excellent

Alyssa F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just right

We gathered with extended family for a week and the house was fabulous for us. Brian was very helpful and generous. The house is great. We had an incredible time. Would go back again
Stayed 6 nights in Jul 2023
Verified

10/10 Excellent

danielle s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Large Family celebration

We had a great stay at the home. The pool and spa were amazing - but with the home being very tech-savy, it would have been helpful if there were some more detailed instructions on how to use all the home devices in the house manual, as the owners were not always readily available on the phone. But overall it was a great time for all of us!
Stayed 3 nights in Jun 2024
Verified

8/10 Good

William M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Reunion

Great outdoor are for large groups. Heated pool and hot tub right outside home. Terrific large screen tv and surround sound. Upper bedroom for children has low A-frame type ceiling and not much room for luggage
Stayed 4 nights in Jun 2023
Verified

8/10 Good

Tracey M.

Liked: Cleanliness, check-in, communication, location

Comfortable Enough.

Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

BARBARA L.

Liked: Cleanliness, check-in, communication, location

Nuclear family reunion

Our family of 10 had a great time in Brian's beautiful home. Loved the pool, hot tub, and sauna. Dining room table is spectacular—in size, graciousness, and view of the pool. Updated living room is lovely. Everyone enjoyed the reclining chairs in the TV room. Beds were comfortable. Only issue for me was that kitchen cupboards were overcrowded. Not enough space to access pots, trays, etc. easily.
Stayed 4 nights in Aug 2023

About the host

Hosted by Brian Winthrop

Host profile image
Mariella (from Switzerland) and I produce events and cater.

Why they chose this property

Beautiful, private, awesome designer bathrooms with bidets, heavenly sunset views, outdoor all season jacuzzi, game room with pool table and foosball, incredible movie room and beautiful big heated pool. Fully stocked kitchen including spices, condiments and honor bar!

What makes this property unique

Lots of activities, beautiful home and property, lots of privacy, great Sonos sound system throughout the house and many different spaces in the house.

Languages:

English, German

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback