TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12

Guilford, Connecticut
$742 avg/night Minimum Stay 3 Nights
Bed 5

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 3 nights

Min Stay

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. Perfect for retreats, events, and reunions!
PLEASE NOTE: *Property not suitable for children under 8 years old. 2 small dogs allowed with prior discussion and fee of 50 per night. Events to be discussed prior to booking and there is a reasonable event fee. Nightly rate for 6 guests, additional guests pay 60 a night. Please list all guests upon booking*

Treetops is perfect for family reunions, work retreats, rest and relax retreats, yoga retreats, writers' workshops, and even small weddings! Spa services right in town, 5 minutes away. Stroll along the loop trail in our backyard woods, hike in acres of beautiful Westwoods next door, visit the town green with lovely shops, swim at Jacobs beach, have s'mores by the natural stone fire pit, or relax and get some sun by the marine-blue, stone decked pool area with flower garden! Birdwatching, breakfast, yoga, and evening cocktails are best on the spacious wrap-around deck. We also have an incredible library, fireplaces, and even a baby grand piano!

The space
The inside of Treetops is spectacular, where classic and modern styles blend. Antiques are plentiful but so too are modern paintings, sculptures, and other unique art. Our love of indigenous cultures will be obvious, and we don't shy away from colors as well! Beautiful, lush plants give the house a welcoming, homey feel.

Treetops has vaulted ceilings, and an open and spacious floor plan. There is a great kitchen with new appliances, a two-person breakfast nook, and an oversized dining area and living room overlooking the oversized deck mentioned above. Perfect for social gatherings of all kinds! Plentiful windows and slider doors flood the house in sunlight and fresh breezes.

The large living room has a top-of-the-line stereo system, CDs, large Smart TV, impressive fieldstone fireplace, and extensive library. Grab a book and recline on the new sofa while listening to some classical music! From there, walk into the master bedroom with more windows and wooded views, TV with DVD player and huge selection of movies, walk-out deck, and walk-in closet. The tiled bathroom has two sinks, a jetted tub for easing sore muscles, and a great shower/showerhead, with some basic amenities available for your stay.
Then walk into the Blue room, a bedroom with 1 Twin bed and 1 Full bed overlooking the driveway with bureau, bedside table, and bookshelves. Guests in this room will share the master bathroom for bathing but can also use the half bathroom near the front entrance.

A hallway then leads to the newly appointed den, with new TV, sofas, and a second beautiful fieldstone fireplace. There are games and coloring books available in the cabinet.

Across from the den and off the main entrance is the Yellow room. It too is newly renovated and has a Full bed, large built-in desk overlooking the pool, views galore, and a cozy reading nook that can also double as a second place to sleep.

Upstairs are two bedrooms, The Queen, with a queen-size bed, and The Twins with -- you guessed it -- 2 twin beds. Both rooms have bureaus, bedside tables, one or two oversized windows, sound machines, fans, and their own full bathroom. You are really in the treetops up here! Enjoy your stay.

Other things to note
Nightly rate is for 6 guests. additional guests are 60 dollars a night.

We are near some railroad tracks and a few times a day, mostly morning and evening, trains go by. You will definitely hear them if you are awake, but we have never been bothered by them when sleeping.

The Pool is scheduled to be available between Memorial Day and Labor Day weather permitting.

See house rules for additional information.

If we can be of help during your stay, please contact us. Please reach out with any questions! Thanks for choosing Treetops.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Eco-friendly Cleaning Products Provided Recycling Unit Size: 4850 Sq Ft (451 Sq M) Uses Some LED Lighting
  • KITCHEN

    Blender Dishwasher Electric Kettle Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden Outdoor Furniture
  • POOL/SPA

    Fence Around The Pool Heated Pool Outdoor Pool Private Pool
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Hiking Nearby Hiking/biking Trails Nearby Kayaking Nearby Marina Nearby Power Boating Nearby Sailing Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books DVD Player Music Library Stereo Video Library Smart TV
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Games
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Stephen W.

    Submitted Dec 30, 2025

    Stayed Dec 23, 2025

    We arrived late, and Dan turned on the lights and left the front door open for us. Then on our last evening there began a decadal snowfall; we called Dan and said we had to leave by 7 a.m. and could he please have the very long and uphill driveway plowed before then? Sure enough, he arrived with a crew at 6:30 and we left on time. Because the house was in perfect order, we had no need to contact him during our stay.

  • Joe S.

    Submitted Dec 3, 2025

    Stayed Nov 24, 2025

    Beautiful home in great location

  • Jennifer C.

    Submitted Oct 27, 2025

    Stayed Oct 23, 2025

    The house was great, we enjoyed hanging out in the living room with the fireplace. Beautiful house, would enjoy going back.

  • Shannon R.

    Submitted Oct 22, 2025

    Stayed Oct 15, 2025

    The Treehouse is pure magic — it’s become our annual home away from home. Every year, my friends and I return for our much-anticipated getaway, and every time, it feels even more special. The house has everything we could possibly need — comfortably accommodating all eight of us — and the setting is absolutely breathtaking. Surrounded by stunning scenery and just minutes from town, it strikes the perfect balance between peaceful retreat and easy convenience. We can’t imagine our tradition anywhere else — the Treehouse truly has our hearts.Sincerely, The Gilmore Gang

  • William B.

    Submitted Oct 1, 2025

    Stayed Sep 25, 2025

    Very large, beautiful house. Impeccably decorated with antiques, knick-knacks, really nice stuff. Pool was closed when we stayed but looked great. The property Manager and host communicated lavishly and were a pleasure to deal with. The property Manager 9Dan) even found something we left and mailed it back to us. Very comfortable and easy to work with. Enthusiastically recommended!

  • Joseph P.

    Submitted Sep 16, 2025

    Stayed Sep 9, 2025

    What a magical property. We were in town for a wedding and this was a great getaway from the craziness of the wedding party. It has tremendous private areas for our guests to get away for privacy and the pool was a great gathering place. It did not feel like a rental home, it felt like the owner invited over to stay and they stepped away. It had history and was equipped to host a large gathering. We could help sharing the info on the house with people who lived in the area and are looking for a place to put guests, we can't say enough nice things! thanks again Dan and Lisa.

  • Jordan S.

    Submitted Sep 16, 2025

    Stayed Aug 23, 2025

    Staying at Treetops is the highlight of our year. My husband and I and our group of friends have been coming to Guilford for a few years now and it just feels like home. We love it and I can't recommend the property enough.

  • Wayne A.

    Submitted Sep 9, 2025

    Stayed Aug 30, 2025

    Loved the place, great location, very cool house. Booked for next year!

  • Aaron B.

    Submitted Aug 25, 2025

    Stayed Aug 19, 2025

    This is an amazing property that is great for groups. Plenty of sleeping places, great for a remote feeling getaway with town amenities still nearby, fun and quirky decorations, and plenty of gorgeous outdoor space. There is also a hiking trail just next door to the property. The property manager was also prompt and responsive, Would happily recommend to anyone looking for a gorgeous get away.

  • Lisa B.

    Submitted Jul 28, 2025

    Stayed Jul 12, 2025

    This property was perfect for our family gathering. Our teen granddaughters loved their private upper level, while their brother had a nifty off-the-beaten-path downstairs den. The pool was warm, clean and fabulous. Great kitchen. Comfortable beds for all. My 95 year old dad loved reading on the deck. Caretaker Daniel was terrific. Truly a top-notch stay.

  • Bryan D.

    Submitted Jul 13, 2025

    Stayed Jul 7, 2025

    It was a beautiful house. The views were gorgeous. The pool was well maintained and a nice place to hangout, overall wonderful place to stay and unwind. We’d definitely come back.

  • Kristin R.

    Submitted Jul 7, 2025

    Stayed Jul 4, 2025

    We really enjoyed our extended family stay at this house! The house is summer unique and different. Plenty of room for the 10 of us. We loved spending time together grilling and swimming in the pool! Dan, the house manager, was great! Super friendly and helpful. We are excited to stay there again in the future!

  • Kathie R.

    Submitted Jun 19, 2025

    Stayed Jun 11, 2025

    This property had all we needed and more !

  • Joe S.

    Submitted Apr 25, 2025

    Stayed Apr 17, 2025

    Beautiful property. Spacious home with great amenities. Owner’s rep Dan very helpful with any information on local attractions.

  • Annette P.

    Submitted Feb 22, 2025

    Stayed Feb 14, 2025

    This house is amazing! Has everything we needed for our stay and very clean. Dan was accessible and very responsive at all times. Highly recommend!

  • Kristel F.

    Submitted Dec 3, 2024

    Stayed Nov 27, 2024

    The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings.

  • Amanda M.

    Submitted Oct 23, 2024

    Stayed Oct 17, 2024

    This was a great spot to stay with friends, with great separate living areas and a great central living room to gather. The location is minutes from downtown Guilford and was very convenient to do and see everything. I would not recommend bringing small children because there is so much beautiful artwork all around the house, but it’s a beautiful retreat for older kids/teens and adults!

  • Daniel L.

    Submitted Sep 28, 2024

    Stayed Sep 20, 2024

    We stayed at the treetops retreat for a long weekend and we can’t wait to go back. It’s everything you can ask for and more. Dan was a great host with amazing communication. My wife and I got married on Friday night and had a bbq there with family and friends on Sunday. Plenty of space for a large family gathering / reunion. The pool and fire pit were a great bonus! Thanks

  • Paul T.

    Submitted Sep 9, 2024

    Stayed Sep 6, 2024

    We held a small engagement party, and the space exceeded out expectations!

  • Trish M.

    Submitted Aug 24, 2024

    Stayed Aug 11, 2024

    Very nice house with lovely outdoor pool area. Very well equipped kitchen and lots of room for entertaining. Short drive to Guilford Green and Docks with lots of restaurant choices. Property's manager was quick to respond and always happy to assist with any questions or requests. As noted in the listing, the train does pass by regularly, which is loud but short lived and not really an issue inside the house. We would definitely consider staying again when we’re back in the area to visit family.

  • Jordan S.

    Submitted Jul 25, 2024

    Stayed Jul 14, 2024

    We are a close group of friends and this is our second stay at Treetops. It is truly an idyllic and wonderful place. The house is extraordinary. It's like staying in a museum! And the pool is incredible. Guilford is adorable and Madison is close by with beautiful beaches. I can't recommend staying here enough.

  • Sean H.

    Submitted Jul 8, 2024

    Stayed Jul 2, 2024

    We had a recent stay at Treetops during a family reunion and it was perfect. It fit a bunch of us and provided a beautiful space to relax. We had a few children in the group and we did make some clear rules at the start as the house is full of amazing artwork that was off limits for the kids. Dan was communicative and a great host. One last tip is that the trails behind the house could fill a whole day of exploring nature. We hope to stay again soon.

  • joseph s.

    Submitted Jun 30, 2024

    Stayed Jun 24, 2024

    Very well appointed and located property. Gracious host. House is very comfortable

  • Alyssondra C.

    Submitted May 27, 2024

    Stayed May 24, 2024

    Treetops is a gem! We celebrated our daughter’s graduation from Wesleyan and the cozy, green, beautiful space was welcoming, spacious and wonderfully decorated. It had plenty of room to gather and be together while allowing grandparents quiet nooks to retreat and regroup. Thank you.

Your dates are Available!

Total

Includes taxes and fees
$742+
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