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100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ

Photo gallery for 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ

Gunite 20x40 Heated Pool, Rose covered fences
Vaulted living room, massive stone fireplace
Exterior
Judd's Bridge, Roxbury
Roxbury Colonial 5 BR - Please click on VIDEO

Reviews

10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 103000 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

2 Twin Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Twin Beds

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area

About this property

100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ

Roxbury & Washington are the best country rural retreats within 1.5 hours of NYC - the best restaurants, shopping, land preserves, Lake Waramaug State Park & Beach, and nearby Mohawk Mountain Skiing. If you are searching for the perfect country escape in a meticulously restored country home on scenic dirt road with a barn, stream, and pond, Roxbury Colonial is for you! The home features a stainless steel chef's kitchen, vaulted barn style living room with giant granite fireplace, oak beams, wide floor boards, library, home theater, wine cellar, and a heated pool surrounded by a large blue stone terrace with a gas barbeque, lounge and dining areas. The vaulted over-sized master bedroom features a granite enclosed over-sized waterfall shower, soaking tub and dual sinks.

Flat screen tvs, home theater, wifi, central heat and air conditioning, down feather beds, comforters and pillows, Frette cotton sheets and bathrobes are just a few of the luxury amenities you will enjoy.

The location is on a scenic dirt road - a great walking, running and biking neighborhood in Roxbury, near the Washington town line in historic, rural Litchfield County. Roxbury is one of Litchfield County's most beautiful rural towns - home to well-known actors, artists, and writers. The home is within a few miles of the Relais and Chateau Mayflower Inn and Spa and Winvian Inn and Spa - perfect for enjoying the best fine dining in New England and the Gunnery Prep School and Washington's historic green. In addition to numerous other popular restaurants, close by are antique shops, wonderful boutiques, art galleries, farm stands, golfing, hiking, fly fishing, canoeing/kayaking/tubing, Mohawk Mountain Ski Area and Lake Waramaug.

Within an hour are the cultural centers of Lenox MA, Hartford CT and New Haven (Yale).
Washington and Roxbury are an easy low traffic 1 3/4 hour drive from NYC or Boston.

Maid service ($25/hour), catering, baby sitting are available for an additional charge.
Pets are welcome.

Master Bedroom: King Bed with private Master Bathroom
Bedroom 2: Queen Bed
Bedroom 3: Queen Bed
Bedroom 4: Two Twin Beds
Bedroom 5: Two Twin Beds



Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi

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House Rules

Check in after 3:00 PM
Check out before 12:00 PM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted
Monthly Rentals have an additional Utilities, Pool Cleaning & Heat, Mowing, Plowing Deposit required.
Weekday rates may be only in conjunction with a weekend booking – please request a quote.
Short-term bookings under one month in duration are only accepted 1-30 days before arrival. Holidays have special rates and minimum stay requirements.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Roxbury

Located in Roxbury, this vacation home is in a rural area and on a river. Institute for American Indian Studies Museum and Research Center and Glebe House Museum and The Gertrude Jekyll Garden are cultural highlights, and some of the area's activities can be experienced at DiGrazia Winery and Valley Golf Center. Traveling with kids? Consider Hollister House Garden and Quassy Amusement Park. Enjoy the area's slopes with cross-country skiing, snowboarding, and skiing, and don't miss out on the ice skating.
View more Vacation Homes in RoxburyOpens in a new window
Map
Roxbury, CT

What's nearby

  • Institute for American Indian Studies Museum and Research Center - 5 min drive - 5.3 km
  • Steep Rock Preserve - 9 min drive - 7.4 km
  • Candlewood Lake - 17 min drive - 17.3 km
  • Lake Waramaug - 17 min drive - 19.3 km
  • Elephant's Trunk Flea Market - 17 min drive - 19.4 km

Getting around

  • Appalachian Trail - 40 min drive
  • Oxford, CT (OXC-Waterbury - Oxford) - 24 min drive

Restaurants

  • ‪McDonald's - ‬15 min drive
  • ‪Starbucks - ‬15 min drive
  • ‪Bridgewater Village Store - ‬10 min drive
  • ‪Dunkin' - ‬16 min drive
  • ‪Three Brothers Family Restaurant - ‬15 min drive

Frequently asked questions

Does 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ have a pool?

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

How much does it cost to stay at 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ ?

As of Apr 6, 2026, prices found for a 1-night stay for 2 adults at 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ on Jun 25, 2026 start from $889, 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 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ ?

Check-in begins at 3:00 PM.

What time is check-out at 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ ?

Check-out is at 12:00 PM.

Where is 100% ROXBURY! PoshPadsCT "JUDD'S BRIDGE" 1.5Hrs NYC, 5BR, Ski, Pool, Pond, BBQ located?

This family-friendly Roxbury vacation home is located on a river, 2.7 mi (4.4 km) from Institute for American Indian Studies Museum and Research Center, and within 6 mi (10 km) of Steep Rock Preserve and Lake Lillinonah. Glebe House Museum and The Gertrude Jekyll Garden and Hollister House Garden are also within 9 mi (15 km).

Reviews

10

Exceptional

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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jennifer R.

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

Wonderful Spring long weekend

Loved the house. Great location. Stephen was a fabulous host. We will be back
Stayed 4 nights in May 2019
Verified

10/10 Excellent

Katherine B.

Perfect Place for a Weekend Away

We had a lovely time! The property looks even better than it did in the photos and the pool was the ideal place to hang out! We are already discussing going back!
Stayed 2 nights in Aug 2018

About the host

Hosted by Stephen Brighenti

Host profile image
I am in the luxury boutique hotel business and saw the need for luxurious accommodations for vacationers to Washington and Roxbury. I have restored and furnished and currently rent 9 homes in these wonderful Litchfield County communities. Each is furnished like a luxury hotel - the best bedding - down featherbeds, comforters, and pillows with Frette all-cotton sheets, bath linens, and bathrobes. All bathrooms are new with nickel bath fixtures. New high-end kitchens, art, antiques and great amentities.

Why they chose this property

This location is one of the best in Roxbury on a country dirt road that leads into a 1000-acre land preserve yet close to the Mayflower Inn and Spa and great dining options, skiing, lakes and more.


Roxbury & Washington are located in historic, rural Litchfield County, within a scenic 2-hour drive from NYC and is exceptional for its excellent restaurants, spas, antique shops, art galleries, boutiques, farms, historic homes, gardens, vineyards, distilleries, and orchards. The Gilmore Girls creator modeled Stars Hollow, the perfect Connecticut town, after Washington and the Independence Inn after the Mayflower Inn. It is the current or former home to many artists, writers, actors and Wall Street executives – referred to as "more Vermont, than Vermont" and "the un-Hamptons". Nature preserves, Lake Waramaug, and the Shepaug River offer extensive hiking, biking, and water activities. Mohawk and Sundown Ski Areas , Lime Rock Raceway, and Quassy Amusement Park are all a short drive. ExploreWashingtonCT and PoshPadsCT have the best listings of area amenities and event calendars. (Note that VRBO-HomeAway's map needs to be zoomed to really show Washington and Roxbury listings only and not homes 30 minutes away in less desirable locations.)
All of my homes in Washington and Roxbury (PoshPadsCT) are beautifully landscaped with flowering shrubs, flagstone terraces with gas bbq. And heated pools. They are furnisged with Frette pressed cotton sheets, plush towels and bathrobes, down featherbeds, comforters and pillows. Optional maid and catering and massage services are available. All homes have Central heat and AC, WiFi, flat screen televisions with dvds, cable and movie channels, and central alarms.

A car is necessary to enjoy rural Roxbury, Washington and Litchfield County.
The nearest bus station is Southbury, 15 minutes away.
The nearest train stations are in Amenia and Wingdale NY or Danbury or New Haven CT – all about 45 minutes away.

Languages:

English
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