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Country Estate: Main Lodge-4 Bdrms, 3.5 bath. Optional Cottages-4 Bdrms, 2 bath

Bedrooms 4
Half Baths1
Space 3,000 sq. ft.
Property type house
Minimum Stay 2 - 3 nights


About the property

Main Lodge -4 bedroom & 3.5 bath; Optional Brookside Cottage & Brookside Lodge

Located at the end of a winding country road and nestled against the base of Mount Anthony, the property has 350+ private acres to hike or walk, two lovely ponds for swimming, stunning views of Pleasant Valley from the wraparound front porch, and spacious, modern living quarters. The property includes two residences. The main house (pictured above) has 4 bedrooms and 3.5 bathrooms with first and second floor master bedrooms with king beds and en-suite bathrooms. The 2 additional bedrooms share a hall bathroom complete with jacuzzi tub. There is a modern, gourmet kitchen with vaulted ceilings and skylights and floor-to-ceiling, fieldstone, wood-burning fireplace. This well appointed home can accommodate up to eight adults.

Also located on the property is separate lodging, the Brookside Cottage, which can be rented for $250/night as additional accommodations for up to 4 adults. The Brookside Cottage (see final photos of our listing) has a gourmet kitchen, open floor plan, wood-burning fireplace, 2 bedrooms, and 1 bathroom.

Here you can enjoy a wide range of sporting, cultural, and restful activities. The expansive acreage of our estate includes clean, crisp ponds for swimming and trails that will lead you across the fields and into the woods and hills. With Pleasant Valley Country Estate as your base of operation, you may enjoy the delights of Southwestern Vermont and return to your luxurious and inviting “Green Mountain” home.

Our gourmet kitchens are fully equipped for your cooking pleasure. Concierge services, such as pre-arrival food shopping, appointments for spa treatments, and catering are available upon request. We can help make your visit easy, carefree, and relaxing.

On the property and in the the Bennington area, there are many activities:

- Hike or bike the trails on our 350+ acre private estate preserve

- Swim each day in the refreshing ponds

- Pick your own fruits and vegetables

- Cross-country ski and snow shoe on untouched snow

- Relax and enjoy the views of the ponds and the valley beyond

- Enjoy nature at its finest

Tour the local Bennington area and visit covered bridges, historic homes, the Bennington Battle Monument, Bennington Pottery, Bennington College, and local museums. Williamstown, Tanglewood, and the Berkshires are all in nearby providing additional cultural activities.

Also, you may:

- Golf at beautiful Mt Anthony Golf Club

- Horse-back ride on local trails

- Canoe or fish the renowned Battenkill River

- Visit one of the area's sugar shacks to see sap turned into maple syrup.

- Ski the mountains of Southern Vermont: Bromley and Stratton are only 30 minutes away and Mount Snow is only 45 minutes away.

Pleasant Valley Country Estate is a wonderful place to visit and enjoy at any time of the year and in any season.

More Details

Property Manager
Justine Robertson
Member since: 2009
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
July 18, 2017

Guestbook comments from the manager

We came up to enjoy a little family time with the new baby & the Irish Music Festival & Garlic Festival. The house was amazing-awesome to give everyone their own space & still let everyone enjoy each others company. Perfect distance from the festivals. We ran & biked every day. Great scenery, beautiful grounds-great for family photos. Everyone cannot wait to come up next year. Maybe the baby will even swim in the pond!
Sep 2010
  • 1 of 8


Bennington House Accommodation and Amenities

Property Type:
  • house
  • Catering available
  • Housekeeper Optional
Floor Area:
  • 3000 sq. ft.
House Rules:
  • Max. occupancy: 8
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Mountain
  • Mountain View ...
  • Rural ...
  • Village ...
  • Water View ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer ...
  • Fireplace ...
  • Firewood
  • Free Long Distance
  • Hair Dryer
  • Heating ...
  • Iron & Board
  • Laundry Soap
  • Linens Provided ...
  • Living Room ...
  • Local Activities Guide
  • Local Maps
  • Local Restaurant Guide
  • Paper Towels
  • Parking ...
  • Parking Off Street ...
  • Telephone ...
  • Telescope
  • Toilet Paper
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet
  • Wood Fireplace ...
  • Catering Available ...
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils ...
  • Dishwasher ...
  • Freezer ...
  • Grill
  • Ice Maker
  • Kitchen ...
  • Lobster Pot
  • Microwave ...
  • Oven ...
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 3 Bathrooms
  • 1 Half Bath
  • Main House Bathroom 1 - toilet , tub , shower , in Bedroom 1
    Main House Bathroom 3 - toilet , tub , shower , jetted tub , off 2nd floor hallway
    Main House Bathroom 4 - toilet , first floor
    Main House Bathroom 2 - toilet , tub , shower , in Bedroom 2
  • Main House: Bathrooms are extra large, and have luxurious stone shower stalls with separate soaking bathtubs. Upstairs shared bathroom has full washer, dryer and laundry sink for guest use if desired. Brookside Cottage: 1 full bathroom. Brookside Lodge: 1 full bathroom
  • 4 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 king , 2nd floor
    Bedroom 2 - 1 queen , 2nd floor
    Bedroom 3 - 1 queen , 2nd floor
    Bedroom 4 - 1 king , 1st floor
  • Main Lodge: Bedroom 1 and Bedroom 4 are king master suites with en-suite bathrooms containing over-sized marble showers and separate tub. Bedrooms 2 and 3 in the main house share a bathroom off the main hallway on 2nd floor with shower and whirlpool tub. Brookside Cottage: The queen bedded and twin bedded rooms share a bathroom.
  • Books ...
  • CD Player
  • DVD Player ...
  • Games ...
  • Music Library ...
  • Piano
  • Ping Pong Table
  • Radio
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Toys ...
  • Video Library ...
  • Beach Chairs
  • Beach Towels
  • Bicycles ...
  • Deck / Patio
  • Golf ...
  • Kayak / Canoe ...
  • Lanai / Gazebo ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Outdoor Grill Gas
  • Porch / Veranda ...
  • Ski & Snowboard ...
  • Tennis ...
  • Unscreened Porch / Veranda
  • 1 bicycles
  • 10 garden chairs
  • suitable for elderly or infirm
  • wheelchair accessible
Pool / Spa:
  • Private Pool ...
  • Spa Whirlpool
  • jetted tub ...
Onsite Services:
  • Concierge
  • Massage
  • Private Chef
  • autumn foliage
  • caves
  • churches
  • cinemas
  • festivals
  • forests
  • health/beauty spa
  • library
  • live theater
  • museums
  • playground
  • pond
  • recreation center
  • restaurants
  • synagogues
  • theme parks
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • horseback riding
  • horseshoes
  • outlet shopping
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cross country skiing
  • cycling
  • equestrian events
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • ice skating
  • jet skiing
  • kayaking
  • mountain biking
  • mountain climbing
  • mountaineering
  • racquetball
  • rafting
  • rock climbing
  • skiing
  • snowboarding
  • snowmobiling
  • swimming
  • tennis
  • water skiing
  • water tubing


Wonderful! 4.9/5 -
(29 traveler reviews)

89% Complete
10% Complete
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Country Estate: Main Lodge-4 Bdrms, 3.5 bath. Optional Cottages-4 Bdrms, 2 bath
average rating of 4.8965516 based on 37 reviews

Great house

  • 4 of 5

House is beautiful and spacious. It has a nice fireplace which is well stacked. House is on a rather large property and a lot of privacy. The only small issue is the stove. If you need to cook something it doesn't work all that well and takes forever for even water to boil (felt like we were in Colorado in high altitude). Otherwise house is just beautiful.

  • Submitted: Jan 13, 2017
  • Stayed: Dec 2016
  • Source: HomeAway
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Peaceful, gracious, spacious, and clean - perfect stay in a perfect location

  • 5 of 5

Our weekend stay at the estate was picture perfect. The property is secluded and expansive, with amazing views and plenty of room for activities. The house was exactly as described, and even more impressive than the photos. There was more than enough room for the ten of us to congregate on the porch and in the kitchen. Every room was meticulously clean and kitchens and bathrooms were well stocked.

Location was also perfect: A strenuous hike was only ten minutes drive, the cozy town of Bennington even closer.

Communication with the owner and caretaker was very easy and Vinny was very responsive to our questions. I would highly recommend a stay at the Country Estate.

Thanks again!

  • Submitted: Sep 29, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your lovely review of your stay at Pleasant Valley Counntry Estate. We love to share this unique property with wonderful guests like you. Justine Robertson, owner
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Greenfield MA

Beautiful House with Breathtaking Views

  • 5 of 5

This gorgeous house was perfectly located just minutes from downtown. The views from this property were absolutely beautiful. The amenities were perfect, we had all we needed. The house included hairdryers, cooking supplies, cable, and internet. The floor plan was open and spacious. My husband and I stayed here for our wedding, including some of our bridal party. This house will hold some of the most special memories for us always.

  • Submitted: Sep 29, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
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Milwaukee, WI

Beautiful country home!

  • 5 of 5

This property is beautiful and was perfect for our family getaway. The property is expansive and had plenty of room for our kids to run and explore. The caretaker was very kind and ensured that we had everything we needed. The home is well-equipped.

  • Submitted: Sep 6, 2016
  • Stayed: Aug 2016
  • Source: HomeAway
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Pleasant Valley Estate is a slice of heaven!

  • 5 of 5

We came for five days with our family of 6. One of our sons had soccer training in Bennington so the house was perfectly located. From the minute we arrived the kids were obsessed with catching (and releasing) frogs in the pond, and exploring the scenic property.

Situated on 200+ beautiful acres the views never got dull. Each morning we enjoyed the views of expansive rolling hills, ponds as we sipped our coffee from the back porch.

House is in amazing shape, looks brand new. Super comfy beds and top of the line renovated bathrooms . Expansive kitchen with high end appliances, stocked with pans, cooking accessories, pretty much anything you could want/need!

Basement with ping pong for all to enjoy, TVs in most bedrooms and good Wifi.

About 30 minutes to Manchester, Bromley so tons to do - shopping, hiking, river rafting down the battenkill. Bennington Mounment 10 min away for history buffs. Major food shopping 10 min.

Justine and Stephanie were wonderful to deal with, as was Vinny. We can't wait to come back!!

  • Submitted: Aug 21, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for this lovely review. We welcome your return visit
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Relaxing Getaway

  • 4 of 5

We used the main house, cottage, and efficiency for our girls' weekend. Each of us was able to have our own room. It had large spaces, inside and out, where we could gather, as well as plenty of space to be alone. The property is beautiful and conducive to relaxing, enjoying nature, or being active. We were pleasantly surprised to find our one co-worker taking advantage of the piano. The property is spacious and well-maintained. The owner was very concerned about our comfort and enjoyment, as was shown in the texts and phone call. We enjoyed our short stay immensely and cannot wait for our next girls' weekend. We would highly recommend this property for a weekend getaway or a longer stay.

  • Submitted: May 1, 2016
  • Stayed: Apr 2016
  • Source: HomeAway
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Nearest Airport
38 Miles
Albany International Airport
Nearest Golf
1 Miles
Mt. Anthony Country Club
Nearest Train
39 Miles
Amtrack, Rensselaer, (Albany) NY
Nearest Motorway
5 Miles
Route 787, NY
Nearest Restaurant
1 Miles
The Bennington Station
Nearest Ski
30 Miles
Bromley Ski Area; Stratton Ski Area
Car: necessary

Bennington is an easy drive from NYC, NJ, & CT and uniquely situated between Albany, NY, Williamstown, MA and resort areas of Vermont. Enjoy theater, music, fine dining and recreation in this area. Bromley and Stratton Ski areas are only 30 minutes away. Whatever your plans include, you can easily get there from Bennington. Southern Vermont boasts many State Parks, lakes and trails as well as a quaint downtown area for shopping and dining. The closest airport is Albany, NY, an easy 50 minute drive from Bennington.


Rates & Availability

Bennington House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Labor Day weekend
Sep 1 2017 - Sep 4 2017
2 night minimum stay
Notes: Rates are based on 4 guests; add $50 per night, per additional guest
Fall Foliage
Sep 22 2017 - Oct 23 2017
2 night minimum stay
Notes: Rates are based on 4 guests; add $50 per night, per additional guest
Nov 22 2017 - Nov 26 2017
3 night minimum stay
Notes: Rates are based on 4 guests; add $50 per night, per additional guest
Dec 20 2017 - Jan 2 2018
2 night minimum stay
Notes: Rates are based on 4 guests; add $50 per night, per additional guest
My Standard Rate
2 night minimum stay
Notes: Rates are based on 4 guests; add $50 per night, per additional guest

Additional information about rental rates

Refundable damage deposit $1,000
Cleaning fee (mainhouse) $150
Tax Rate 9.0%

Holiday Rates also apply to July 4th, Columbus Day & Veterans Day. The "Instant Quote" calculator will give you an approx. cost for your group. Actual cost & damage deposit will depend on whether you rent the Brookside Cottage in addition to the main house. We do not charge for children under 2 yrs. old. Please E-mail manager to obtain a precise rental quote.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Contact Manager

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