Entire home

A country guest house just 21-32 minutes Bridgeport or New Haven Universities.

Photo gallery for A country guest house just 21-32 minutes Bridgeport or New Haven Universities.

A cozy living area with a stone wall, wooden flooring, a sofa, a dining table with chairs, and a bench.
A dining area with a wooden table and chairs, large windows, and a view of a garden.
A paved pathway leading into a lush garden with a large tree and a potted plant.
A living room with a stone fireplace, wooden flooring, a glass coffee table, a sofa, and a television on a wooden stand.
A bedroom with a wooden floor, a bedside table with a green lamp, a patterned bedspread, and a wooden headboard.

Reviews

8.8 out of 10
Excellent

Highlights

  • Family fun awaits
    Top-rated for families.
  • Sledding nearby
    A rare find — snowy slopes for sledding are just minutes away.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Internet
  • Refrigerator

Explore the area

View in a map
Shelton, CT
  • Place, Indian Well State Park
    ‪4 min drive‬
  • Place, Osborndale State Park
    ‪6 min drive‬
  • Place, Monroe Plaza Shopping Center
    ‪7 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
    ‪38 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Separate dining area
Garden
Dining area

About this property

A country guest house just 21-32 minutes Bridgeport or New Haven Universities.


Welcome to Pleasant Valley Trails! A rustic Mid-Century home on a 41 acre scenic property overlooking a 2 acre pond. The home was built from the wood and stone taken from the property. This is an ideal place for relaxing and spotting a variety of wildlife that like to visit.

Located in the White Hills section of Shelton, you'll find our comfortable two-bedroom getaway. Park in the driveway by white front door for easy access. As you step inside, you'll be greeted by the warmth of the fireplace, the westerly view and the convenience of free WiFi, a washing machine, and a smart TV for your entertainment.

In the fully stocked kitchen, you can whip up delicious meals using the stove, oven, refrigerator, grill, and an array of helpful appliances like the microwave, lobster pot, coffee maker, and blender. Savor your creations at the dining table, surrounded by the serene views outside.

When it's time to unwind, sink into the comfortable living room or step outside to enjoy the patio and outdoor furniture. Indulge in some games or dive into a good book. With the essentials like towels, basic soaps, and a hair dryer provided, you can focus on creating lasting memories during your stay.

Pleasant Valley Trails is nestled in the country between pick-your-own farms. You can get summer berries, autumn apples, pumpkin, baked goods, cider, and holiday Christmas Trees. There are also a nearby winery and a distillery (open weekends) that use locally grown produce for their products.

If up for a a walk, enjoy the public trail ( from sunrise to sunset) that crosses our wooded acres to the north west and connects to other public hiking trails to the southeast. Pleasant Valley Trails is part of Shelton's 28 mile trail system. Yet, we are only a short drive (14- 15 miles) to Bridgeport or New Haven, and close to fresh water or salt water beaches.

More local information such as restaurants, stores, activities, etc., can be found in our guest book kept on the kitchen counter nearest the dining area.

We hope you will enjoy your stay!
Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

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

Similar properties

Bedroom 1
3BR Gem, 10 min to Yale, walk to Tweed
East Shore
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
8.8 out of 10, Excellent, (6 reviews)
3BR Gem, 10 min to Yale, walk to Tweed

House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
default

Children

Children allowed: ages 13–17
Please inform me of children < 12 years old
default

Events

Events allowed: family gatherings and birthday parties
default

Pets

Pets allowed: dogs less than 9 kg per pet (limit one pet total)
default

Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
See the Guest Handbook for explicit details .
Failure to complete these may result in a negative review from the host.
Remove outdoor shoes and leave them by entrance door. Adjust heat by thermostat in dining area . Return heat setting to 50° F before checking out.
Before Checking Out: Strip beds of used sheets and pillow cases & leave in wicker hamper in laundry area. Put used towels & wash cloths on the tub.
Put recycling in blue bin, bagged garbage in brown bin outside, bins at the road Wed. pm Lock all outside doors, close windows, put key in the lockbox

Important information

You need to know

Property Registration Number 1923016
Property # 1923016vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 10
Long-term renters welcome
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, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Shelton

Located in Shelton, this holiday home is in a rural area and by the sea. Boothe Memorial Park and Museum and Perry House are local landmarks, and the area's natural beauty can be seen at Indian Well State Park and Osborndale State Park. Looking to enjoy an event or a game while in town? See what's happening at Wolfe Park Tennis Center or Campus Field. Enjoy the area's slopes with cross-country skiing, and don't miss out on the sledging and ice skating.
View more Holiday homes in SheltonOpens in a new window
Map
Shelton, CT

What's nearby

  • Indian Well State Park - 4 min drive - 4.3 km
  • Osborndale State Park - 6 min drive - 5.7 km
  • Monroe Plaza Shopping Center - 7 min drive - 7.8 km
  • Shelton Dog Park - 8 min drive - 7.4 km
  • SportsCenter of Connecticut - 15 min drive - 14.7 km

Getting around

  • Bridgeport Station - 24 min drive
  • Oxford, CT (OXC-Waterbury - Oxford) - 29 min drive

Restaurants

  • ‪Dunkin’ - ‬8 min drive
  • ‪McDonald's - ‬8 min drive
  • ‪Bill's Drive In - ‬7 min drive
  • ‪Roseland Apizza - ‬12 min drive
  • ‪Dock 34 - ‬15 min drive

Frequently asked questions

Is A country guest house just 21-32 minutes Bridgeport or New Haven Universities. pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

How much does it cost to stay at A country guest house just 21-32 minutes Bridgeport or New Haven Universities.?

As of 22 Sept 2026, prices found for a 1-night stay for 2 adults at A country guest house just 21-32 minutes Bridgeport or New Haven Universities. on 5 Dec 2026 start from £673, 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.

How much is parking at A country guest house just 21-32 minutes Bridgeport or New Haven Universities.?

On-site parking is available at the property.

What time is check-in at A country guest house just 21-32 minutes Bridgeport or New Haven Universities.?

Check-in begins at 3:00 PM.

What time is check-out at A country guest house just 21-32 minutes Bridgeport or New Haven Universities.?

Checkout is at 11:00 AM.

Where is A country guest house just 21-32 minutes Bridgeport or New Haven Universities. located?

Situated by the sea, this holiday home is within 6 miles (10 km) of Indian Well State Park, Monroe Plaza Shopping Center and Housatonic River. Shelton Dog Park and Wolfe Park Tennis Center are also within 6 miles (10 km).

Reviews

8.8

Excellent

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. 17 out of 25 reviews
Rating 8 - Good. 4 out of 25 reviews
Rating 6 - Okay. 2 out of 25 reviews
Rating 4 - Poor. 1 out of 25 reviews
Rating 2 - Terrible. 1 out of 25 reviews

9.0/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.4/10

Location

9.0/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Lovely peaceful

Rustic but great spot in the woods, views, dogwoods in bloom. Old but lovely vibe and great location, winery nearby.
Stayed 5 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very scenic place with an amazing backyard and atmosphere.
Stayed 7 nights in Jul 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is absolutely gorgeous, beautiful view and very private. The house is rustic, but very clean. Communication with Jill was flawless and check in/out is very easy.Beautiful fireplace, wood can be purchased just up the road at a reasonable price. We stayed a month and have already rebooked. If you are looking for a clean house, good location, great views, you will be happy here, if you are looking for brand new not for you. As far as children go, I think 8 and up would have a great time. Fishing, trails, canoe, exploring. Would not recommend for toddlers.
Stayed 28 nights in Feb 2026
Response from VrboOwner on 1 Apr 2026
Thank you for your review. I appreciate your taking good care of the house and communicating well. The spring and summer offer much better access to the trails when there is as much snow as we had this winter. When the weather is cold or rainy it is nice to be inside and cozy by the fireplace. I'm glad you enjoyed the view. There will be more wildlife to see with the warmer weather. Also, local U-Pick farms will be active starting in mid June berry picking in the fall for pumpkins and until through December with winter decor and Christmas trees.. I welcome you to visit in any season!
Verified review

10/10 Excellent

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

Christmas stay.

Beautiful view with all the amenities. We would definitely come back to this place when in town again.
Stayed 3 nights in Dec 2022
Verified review

10/10 Excellent

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

Beautiful private retreat

We had a wonderful stay. Jill was very responsive to some minor issues. Great to check in and out easily. Definitely would stay there again😊
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

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

Pleasant Thanksgiving getaway.

Our stay was a pleasant, relaxing Thanksgiving long weekend in the woods. We enjoyed serene hikin g trails.All amenities / utilities worked well. The kitchen was well stocked
Stayed 5 nights in Nov 2024
Verified review

10/10 Excellent

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

Amazing

Highly recommend
Stayed 31 nights in Dec 2020
Response from VrboOwner on 13 Feb 2021
Thank you, Sara. I am pleased to find that you enjoy the property and the trails as well as the house. Jill
Verified review

2/10 Terrible

Disliked: Cleanliness, check-in, communication, location, listing accuracy
Driveway wasn't sanded, Doors were frozen shut, electrical outlets didn't work, no smoke detectors, microwave, washing machine didn't work. Appliances were circa 1975, toilet didn't fill...
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

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

Great Location for Wedding weekend stay

This home is conveniently located for a wedding at The Waterview. I wanted a local home for a stay with my older parents and husband and this was perfect. We had events at Candlewood Lake as well as the wedding at The Waterview and this home was perfectly located. The home was clean and the setting is lovely. We had everything we needed. We couldn't beat the price and having a home is always much more convenient when traveling with my parents.
Stayed 4 nights in May 2024
Verified review

8/10 Good

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

Secluded, quiet cabin

Old fashioned quaint cabin with hand made shelving and cabinetry. Very quiet, set in the woods overlooking a beautiful piece of land & pond. Don’t go alone… a bit spooky, but very nice. The place was very clean, but could use some work or updating. If you enjoy nature & a beautiful peaceful setting, this place is great.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

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

Comfortable, rustic stay surrounded by nature

The property sits enough off the main road that it feels secluded. A deer was standing outside one bedroom one morning! Surrounded by woods with a lake in back down a hill. The 1 Q and 2 T beds were fine for the needs of 3 senior citizens. We didn’t cook there, but there were lots of dishes & pans.We enjoyed our stay & would stay again if in the area.
Stayed 4 nights in Sep 2024
Response from VrboOwner on 23 Sept 2024
Thank you for your lovely review, Debra. I am always pleased to hear that my guests enjoyed the property and the wild life at Pleasant Valley Trails. Your group were great guests. I appreciate your suggestions. It was a pleasure to host you and I would welcome you to stay again anytime you are in the area! Sincerely, Jill Bennett
Verified review

10/10 Excellent

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

Quaint and quiet

Home is located back from the road, very quiet. Lots of wildlife outside. Home was built in 1952, all hand made cabinets and lots of built ins. House was very clean. There had been a leak in the roof by the bathroom in the hallway that needs repair. Lots of space inside with a very large eat-in kitchen. Washer and dryer worked great. Easy access to Jones Family Farm and highway.
Stayed 6 nights in Jun 2023
Verified review

10/10 Excellent

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

Away from it all

My husband and I go to a music festival about 20 minutes from this house. We enjoy the house almost as much as the festival. The house is charming and has a rich history. I feel like I’m visiting a house my Great grandparents built. It’s absolutely gorgeous. I love all the windows and rock fireplace. The view of the pond is an added plus. This is our second year, attending the festival, and being at the house. We hope to make it a tradition. 5 Stars hands down. I’d give it more if I could!
Stayed 4 nights in Sep 2023
Response from VrboOwner on 21 Oct 2023
Thank you so much for your great review. I'm glad you enjoy the house and the property! It was nice to have you visit again. You and your husband are welcome to visit at Pleasant Valley Trails anytime!
Verified review

10/10 Excellent

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

A piece of heaven ✨️

We came to Connecticut from California to look at colleges. I found this gem and couldn't resist its beautiful charm. The house is surrounded by beautiful tree-lined roads and a very serene view out the windows from the kitchen to the living area. There is a pond in which geese , turtles , and fish live. It was very comfortable and ideal if you appreciate nature and quiet surroundings. The only thing I would recommend is curtains in the living area. It truly was a memorable stay! The owner is very nice, easy to reach if needed. 👍👍🙌
Stayed 6 nights in Apr 2023
Response from VrboOwner on 26 Apr 2023
Thank you for your lovely review. I always like hearing that my guests enjoy the nature and the wild life on the property of Pleasant Valley Trails. Considering your suggestion, will look into getting some shades for the long windows in the living room dining room area that gets the evening sun.
Verified review

6/10 Okay

Liked: Check-in, communication, location

First Experience in Shelton

This property was built in the 1950’S and needs a lot of updating. The furniture on the website was different from what was in the house. There was a grill that was not useable. The house some insect issues but we’re resolved by an exterminator after we contacted owner. There were other issues but the owner took cate of them in a timely manner. Very quiet area. Roku TV was hard to operate. We had Xfinity in FL so we could get some TV. Overall it is a very quiet and secluded home. Owner very responsive to any issues we had.
Stayed 91 nights in Jun 2021
Verified review

6/10 Okay

Liked: Check-in, communication, location
Disliked: Cleanliness

Secluded but a bit dilapidated

The seclusion and privacy of the property is certainly there, though a security gate or at a minimum a “private drive” sign would have given some added peace of mind. There were kids drink straws and pieces of trash in the driveway upon arrival, tiles on the sidewalk were broken and many of the light fixtures didn’t work. The large windows looking out toward the pond were very dirty and the outside framing was rotting away. The back porch tile was falling apart and two of the doors headed out back opened to areas you would not want to step into. One of the beds had a broken box spring and mattress that leaned heavily to the side. The floor in the hallway had a trapdoor that is hidden until it pinched my wife’s toe so bad it made it bleed (found it was a large hinged panel in the floor with the light from the phone while investigating what cut her). The place has potential, it is just a bit dilapidated for use as a rental.
Stayed 4 nights in May 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location

Wake up with the sun!

The unit is in a nice area in the country but after I found a tick on me in February we didn't go out. The owners live in the attached unit next door, separated only by a wooden door so ALL the sound goes both ways. You can hear them put dishes away and talk--but rarely--they were super quiet most of the time. They never complained about us being noisy although my son kept later hours due to the time change and could occasionally be loud because of medical issues. The host was responsive and ordered a us a crock pot for our stay when I asked. She met us when we arrived and opened the lock box. Go slowly up the driveway as there is a drainage dip and bumps that cars might bottom out on if low to the ground. The curtains in the master bedroom aren't lined but seem to keep out most light except that they aren't wide enough to cover the windows. I rigged towels, pillows, and a chair to cover the remainder of the window. The kids/twin beds room is terrible though with only white unlined curtains around 2 sides of the room so my 13 year old son couldn't sleep well at all after the sun came up since it was so bright. He said the twin beds at first seemed comfortable but weren't. The queen was fine. Liked the wood floors but they do creak loudly and are uneven in places. You can't turn the WIFI off but can unplug the extender which decreases it. Sign into your own accounts for TV/movies--or maybe I just couldn't figure it out. Plenty of pots and pans and dishes. BYO bedside clocks.
Stayed 12 nights in Feb 2023
Verified review

4/10 Poor

Liked: Check-in, communication
Disliked: Cleanliness, location, listing accuracy
The site is on approximately 40 acres and a clearing at the top of the hill.The property was a shambles. An old greenhouse has pieces of broken glass, all around the ground. A old tractor was outside the bedroom window. It was used to mow The lawn twice in two months. We had. to buy our own lightbulbs. We had to freeze ice and metal bowls and then chop up, place in the dispenser, then press the button to deliver ice.The landlord was very friendly and polite, in answering our questions and trying to solve our problems. However, she was managing the property from out of state and had no one reliable to be able to solve some of our problems. These are the reasons for our review.
Stayed 61 nights in Jul 2026
Verified review

10/10 Excellent

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

Recommend

Good stay and nice lake to look at. When things are not working, they get fixed rather quickly
Stayed 31 nights in Oct 2022
Verified review

10/10 Excellent

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

Unique and Private

My husband and I loved this property. It is surrounded by trees and the views out of the many large windows of the pond is just beautiful. The stone fireplace and gorgeous wood floors make this house unique. I’d love to go back again!
Stayed 3 nights in Sep 2022
Verified review

10/10 Excellent

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

Absolutely amazing!

We were in CT for Christmas and we needed a lace with 2 bedrooms so that my 5 year old and 19 month old could sleep (and not keep each other awake). What we got was do much more. We got a beautiful view, a great place for piddle jumping and leaf throwing, and a warm and cozy place. Thank you for allowing us to stay there and for giving us the history of the property! We had an absolutely great time!!!
Stayed 6 nights in Dec 2021
Verified review

8/10 Good

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

Western Connecticut Exploring

Older property set well off the road with a beautiful view of a serene pond. We found the location excellent for exploring the beautiful Western Connecticut countryside.
Stayed 7 nights in Oct 2021
Verified review

10/10 Excellent

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

Great view

The property is very pretty and we enjoyed the fireplace.
Stayed 3 nights in Nov 2020
Response from VrboOwner on 6 Dec 2020
It is lovely to sit by the warm fireplace when the weather is chilly. I'm glad you enjoyed it!
Verified review

10/10 Excellent

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

Pleasant Valley Trails

Very nice and attentive property owner. Property is perfect for R & R. Quiet and peaceful wooded location. Would stay again.
Verified review

10/10 Excellent

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

Amazing stay

It is a great house with an incredibly picturesque view. There is a large pond surrounded by a forest that can be seen from the house and it is a difficult view to leave behind. Will stay again.
Stayed 2 nights in Oct 2020
Response from VrboOwner on 3 Nov 2020
Thank you for your lovely review! I am pleased that you enjoyed your stay. I will be happy to have and your group visit Pleasant Valley Trails again!

About the host

Hosted by Jill S. Bennett

Host profile image

Languages:

English

Premier Host

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