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A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Holiday home in Guilford with private pool and kitchen

Photo gallery for A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Exterior image
exterior image
Front entrance
Pool and gardens image
Pool and gardens image

Reviews

10 out of 10
Exceptional
5 bedrooms2+ bathroomsSleeps 12450.6 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Fireplace
  • Barbecue grill

Explore the area

View map
Guilford, CT
  • Place, Stony Creek - Thimble Islands Historic District
    ‪4 min drive‬
  • Place, Bishops Orchard and Winery
    ‪4 min drive‬
  • Place, Hammonasset Beach State Park
    ‪13 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
    ‪20 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 Double Bed and 1 Single Bed

Bedroom 3

1 Double Bed and 1 Single Sofa Bed

Bedroom 4

1 Queen Bed

Bedroom 5

2 Single Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Jetted bathtub · Shampoo

Bathroom 2

Soap · Towels provided · Toilet

Bathroom 3

Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Garden
Dining area

About this property

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

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 woods in "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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Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 3–17
House is best for children 8 and above.
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
With fee and prior approval. No furniture or pool!
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Smoking

Smoking is not permitted
Age 30 and up to book Children over 8 welcome Guests to leave house in vg condition. Nightly rate is for 6 guests. Xtra guests 60 a nite
Property sleeps 11; only booked guests may stay/visit unless prior auth obtained. AC must be above 74 deg's in summer; below 70 deg's in Fall/Winter
Guests not to use pool heater. Heating pool to 78 is $65 a day. Must sign a pool liability waiver. Dog owners must agree to/sign rules upon arrival

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30
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 and a deadlock

About the area

Guilford

Located in Guilford, this holiday home is in the city centre and near the beach. Bishops Orchard and Winery and Rose Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chaffinch Island State Park and Hammonasset Beach State Park. Looking to enjoy an event or a game while in town? See what's happening at Foote Memorial Park Tennis Center or Connecticut Sportsplex. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Guilford, CT

What's nearby

  • Guilford Town Green - 2 min drive - 2.2 km
  • Chaffinch Island State Park - 4 min drive - 1.8 km
  • Stony Creek - Thimble Islands Historic District - 4 min drive - 4.0 km
  • Bishops Orchard and Winery - 4 min drive - 2.8 km
  • Hammonasset Beach State Park - 13 min drive - 14.5 km

Getting around

  • Guilford Station - 4 min drive
  • New Haven, CT (HVN-Tweed - New Haven Regional) - 29 min drive

Restaurants

  • ‪The Place - ‬4 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Mr. J Asian Bistro - ‬5 min drive
  • ‪Dunkin' - ‬6 min drive
  • ‪Vfw In Guilford - ‬5 min drive

Frequently asked questions

Does A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL! have a pool?

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

Is A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL! pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!?

Check-in begins at 4:00 PM.

What time is check-out at A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!?

Checkout is at 10:00 AM.

Where is A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL! located?

Located in the heart of Guilford, this holiday home is within 2 miles (3 km) of Chaffinch Island State Park, Guilford Town Green and Hyland House Museum. Bishops Orchard and Winery and Henry Whitfield State Museum are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 36 out of 37 reviews
Rating 8 - Good. 1 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Aaron B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025

10/10 Excellent

William B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Sep 2025

10/10 Excellent

Lisa B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 14 nights in Jul 2025

10/10 Excellent

Wayne A.

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

unique house, great location

great stay!
Stayed 8 nights in Sep 2023

10/10 Excellent

Joseph P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Sep 2025

10/10 Excellent

joseph s.

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

Beautiful home and setting

Thoroughly enjoyed my visit. Lovely home, well appointed. Gracious host and responsive manager, Dan. Easy access to local attractions and adjacent to extensive hiking trails. Well worth the visit.
Stayed 6 nights in Apr 2023

10/10 Excellent

Tracy C.

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

Girl’s Getaway

Treetops is a beautiful property that was perfect for a girls weekend. Plenty of room and a lot of unique furnishings and art. Great outdoor space, including a gorgeous pool. Westwoods is in its backyard which offers spectacular hiking. Convenient to downtown.
Stayed 3 nights in Jun 2023

10/10 Excellent

Julianne D.

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

Awesome spot! Truly a treehouse

First visit to Connecticut. Stayed for 4 nights with my adult children and my sisters family for family wedding. Loved everything about the house. Very eclectic with lots of outdoor space next to miles of trails and close to quaint town.
Stayed 4 nights in Aug 2023

10/10 Excellent

Ray D., Peoria

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

Stunning, unique, amazing

By far the most unique architecture that we have ever stayed in. Every room is an adventure from its shape to the stunning artifacts from around the world. A gorgeous setting that was perfect for relaxing. Everything is first class-five star. So memorable that we are coming back next year.
Stayed 6 nights in Sep 2023

10/10 Excellent

Alyssondra C.

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

Peaceful retreat

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.
Stayed 3 nights in May 2024

10/10 Excellent

Gina S.

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

Beautiful in the trees!

We loved this property! In town for a wedding. Property was as listed in the description - plenty of room for all guests and super clean! Large kitchen plenty of areas to relax ( bird watching from the dining table was great!) The pool was wonderful too! Neat layout with multi levels. Only draw back was all of the stairs - we had some older guests in our party (in their late 70’s) that had trouble with the stairs but a younger crowd would not have a problem.
Stayed 5 nights in Jun 2023

10/10 Excellent

Patricia S., Catskills, NY

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

Perfect for family fun and relaxation

Upon our arrival Dan, our kind and gracious host, explained all of the amenities in this amazing home. The entire family had fun in the beautiful pool (especially lovely when it was lit up at night) and all areas of the house. We enjoyed the abundant art, music, and books that were provided. We all had plenty of personal space and comfortable beds. Guilford is a beautiful town and my family raved about the restaurants and stores. We hope to return to this home. It was ,by far, the best vacation home I have ever rented.
Stayed 4 nights in Jul 2023

10/10 Excellent

Jordan S., Boston, MA

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

A curated escape

This house is INCREDIBLE. The pictures do not do it justice. It's like staying in a perfectly curated museum. It's extremely comfortable and lovingly decorated. The space is so unique and inspiring. The decks are lovely for lounging. The pool is amazing. Six adults very comfortably shared the home and we had a great time! There's lots of hiking right by the property and the birdwatching is incredible at the house. Also Guilford is a very quaint and charming town with plenty of diversions and dining. It's the perfect place to unwind.
Stayed 7 nights in Aug 2023

10/10 Excellent

candace d.

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

I could get used to this!

A visually stunning home, inside and out. We found a book that the owner had written, so we were able to find out a lot about the house and the lives of the people who lived here... made it so personal for us. Truly, nothing has been overlooked, just amazing. the ONLY problem? We had to leave! But... we WILL be back! Dan welcomed us to our home and gave us the tour, and was available to answer a couple questions during our stay. Customer Service seems to be a lost art, and we appreciated his helpfulness!
Stayed 3 nights in Jul 2023

8/10 Good

Jennifer C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was great, we enjoyed hanging out in the living room with the fireplace. Beautiful house, would enjoy going back.
Stayed 3 nights in Oct 2025

10/10 Excellent

Shannon R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 4 nights in Oct 2025

10/10 Excellent

Jordan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Aug 2025

10/10 Excellent

Wayne A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the place, great location, very cool house. Booked for next year!
Stayed 7 nights in Aug 2025

10/10 Excellent

Bryan D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 5 nights in Jul 2025

10/10 Excellent

Kristin R.

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

Great stay!

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!
Stayed 3 nights in Jul 2025

10/10 Excellent

Kathie R.

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

Wonderful time with family

This property had all we needed and more !
Stayed 8 nights in Jun 2025

10/10 Excellent

Joe S.

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

Peaceful retreat

Beautiful property. Spacious home with great amenities. Owner’s rep Dan very helpful with any information on local attractions.
Stayed 7 nights in Apr 2025

10/10 Excellent

Annette P.

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

Guilford Stay

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!
Stayed 4 nights in Feb 2025

10/10 Excellent

Kristel F.

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

Thanksgiving Family Weekend

The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings.
Stayed 3 nights in Nov 2024

10/10 Excellent

Amanda M.

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

Great spot for an adult group

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!
Stayed 3 nights in Oct 2024

About the host

Hosted by Dan Casey

Host profile image
15+ experience as a property manager, personable, and friendly.

Why they chose this property

This is a very special property, with a unique, contemporary, exquisitely decorted home, on 2 acres of private wooded and garden grounds, and beautiful in-ground pool. Fireplaces, jacuzzi, extensive library, and baby grand piano make this the perfect retreat.

Premier Host

They consistently provide great experiences for their guests