Entire home

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Riverside holiday home with kitchen and balcony

Photo gallery for Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Exterior
Terrace/patio
Interior
Front of house
Room

Reviews

9.8 out of 10
Exceptional
5 bedrooms2 bathroomsSleeps 8325.2 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Old Saybrook, CT
  • Place, Katharine Hepburn Cultural Arts Center
    ‪2 min drive‬
  • Place, Harvey's Beach
    ‪2 min drive‬
  • Place, Chalker Beach
    ‪3 min drive‬
  • Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
    ‪31 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Bedroom 1 First Floor

1 King Bed

Bedroom 2 First Floor

1 Queen Bed

Bedroom 3 Front Upstairs

2 Double Beds

Bedroom 4--Middle upstairs

1 Single Bed and 1 Double Bed

Bedroom 5 Upstairs back bedroom

1 Double Bed and 2 Single Beds

2 bathrooms

Bathroom 2 Upstairs

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

Bathroom First floor

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

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Gather your people at our 1795 historic homestead near Coastal Connecticut, ideal for reunions, retreats & wedding weekends. Cook & linger in the well-stocked kitchen, read fireside or spread out across the private lawn and porches. A character-rich, memory-making home!

⭐ “Full of character, spacious and comfortable—our family loves coming back.” – Stephen

🏜 HIGHLIGHTS
✓ Authentic 1795 historic estate
✓ Private grounds, porches, firepit
✓ Well-stocked kitchen & cozy fireside spaces

THE SPACE

***Message us for weddings or other large events!***

Historic charm with private grounds, fireside rooms, porches, and a cook-ready kitchen.

🏷 Main Floor

Kitchen & Dining Room
∙ FULLY stocked kitchen w/plenty of counterspace for at-home baking and cooking
coffee maker, tea kettle, blender and toaster
∙ Cooking oils and seasoning essentials
∙ Abundance of dishware, glassware and silverware, including children’s
∙ Full-sized fridge and freezer
∙ Gas stove and oven
∙ Microwave
∙ Dishwasher
∙ Blender
∙ Slow cooker
∙ Dining room table, seating for 4

Living Room
∙ Smart TV
∙ Netflix, Prime Video, Disney Plus, Hulu, HBO and more
∙ Sound system
∙ Fireplace
∙ Board games
∙ Books
∙ Toys

Bedroom #1 (Primary Bedroom)
∙ King size bed
∙ Premium mattress and comforter
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Books
∙ Mirror

Bedroom #2
∙ Queen size bed
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers

Bedroom #3
∙ 2 Double beds
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Books

Bathroom #1 and Laundry Room
∙ GE high-efficiency washer/dryer
∙ Tide Free and Gentle
∙ Shower
∙ Single vanity and mirror
∙ Shampoo, conditioner and body soap
∙ Makeup washcloth

Bathroom #2
∙ Shower
∙ Bathtub
∙ Single vanity and mirror
∙ Shampoo, conditioner and body soap
∙ Makeup washcloth

🏷 2nd Floor

Bedroom #4
∙ Double bed
∙ Single bed
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers

Bedroom #5
∙ Queen size bed
∙ 2 Single beds
∙ Premium mattress and comforter
∙ Room darkening shades
∙ Bedside table and lamp
∙ Large closet w/ hangers
∙ Ceiling fan
∙ Full-length mirror

Hallway
∙ Office table and chair

🏷 Outdoor Space(s)

Sunroom
∙ Large glass roof for natural sunlight
∙ Comfortable sofa
∙ Rocking chair

Backyard
∙ Firepit
∙ Outdoor seating
∙ Play area
∙ Picnic tables and umbrella

Balcony
∙ Outdoor seating
∙ Coffee table

Porch
∙ Enclosed porch
∙ Outdoor seating

🏷 Parking

∙ Room for 6 vehicles but can hold up to 50+ for large events (contact us for details)

🚘 Nearby

Main Street Shops & Boutiques (walking ~3 min): Charming local shopping, antiques, galleries and cafés in the heart of Old Saybrook.
Ashlawn Farm Coffee (drive ~2 min): Local favorite café with specialty coffee, pastries, sandwiches and outdoor seating.
Monkey Farm (drive ~3 min): Popular bar & grill with classic fare and laid-back vibe.
Paperback Cafe (drive ~3 min): Cozy breakfast/brunch spot with community favorites.
Swell (drive ~3 min): Highly rated acai & healthy café option on Main Street.
James Pharmacy Bed & Breakfast and Gelateria (drive ~4 min): Historic gelato and coffee stop with old-town charm.
Fresh Salt (drive ~5 min): Upscale seafood dining with seasonal and local offerings.
Cafe Toscana (drive ~4 min): Casual coffee & tea spot for daytime breaks.
Otter Cove Restaurant & Bar (drive ~7 min): Stylish gastropub with seasonal local menus.
Saybrook South Green & Historic Sites (drive ~5 min): Historic district featuring the Humphrey Pratt Tavern and heritage architecture.
The Kate – Katharine Hepburn Cultural Arts Center (drive ~4 min): Live theater, arts and tribute exhibits to the legendary actress.
Saybrook Breakwater Light (drive ~6 min): Iconic sparkplug lighthouse and peaceful waterfront setting.
Lynde Point Light (drive ~6 min): Historic Long Island Sound lighthouse ideal for photography and scenic views.
Old Saybrook Town Beach (drive ~7 min): Saltwater beach with seasonal swimming and sunbathing.
Harvey’s Beach (drive ~9 min): Popular sandy shore and summer gathering spot on Long Island Sound.
Crystal Lake Town Park (drive ~5 min): Community park with playgrounds, trails and open recreational space.

Tanger Outlets Westbrook (drive ~7 min): Outlet shopping with over 150 brands for fashion and gifts.
Rocky Neck State Park (drive ~15 min): Beach, camping, hiking and nature trails.
Hammonasset Beach State Park (drive ~26 min): Connecticut’s largest shoreline park with miles of sandy beach and boardwalk.
Essex Village (drive ~20 min): Historic small town with antique shops, riverfront views and dining (great half-day trip).

💡 Other things to note
✓ This is a true historic home, full of charm and character, which means you may notice older-home quirks that come with a property from the late 1700s.
✓ The home sits near a main road, so you may hear some traffic at times, though the yard and grounds feel private once you’re settled in.
✓ The beach is ~5 minute drive from the property.
✓ Some areas on the property are reserved for caretaking and maintenance use and aren’t accessible to guests.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

No pets allowed, service animals permitted
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
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
Please message when you leave since we have back-to-back Guests, and the cleaners need to get in to clean. Check-out is at 11:00 a.m. There are no exceptions.
Please clean Outdoor Grill and oven; please do not make the beds. The towels can be started in the washer if you have enough time. Furniture must be put back where you found it
*Pets must be strictly picked up after. *If you use the iron, please empty water from it. *Lint must be removed from the dryer after every use.
Failure to complete these may result in a negative review from the host.
No smoking in the house or green house
Please keep the door to the house shut, either A/C
Please put things back where you have found them.

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: 50
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

We should mention

A car is recommended for transport to and from this property

About the area

Old Saybrook

Located in Saybrook Manor, a neighbourhood in Old Saybrook, this holiday home is in a rural area and on a river. Essex Island Marina and Indian River Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Connecticut Valley Railroad State Park Trail and Ferry Landing State Park. Travelling with kids? Consider Saybrook Country Barn and Stay and Play LLC. Enjoy the area's slopes with cross-country skiing and snowboarding, and don't miss out on the sledging and snowmobiling.
Map
Old Saybrook, CT

What's nearby

  • Katharine Hepburn Cultural Arts Center - 2 min drive - 2.2 km
  • Saybrook Country Barn - 2 min drive - 2.2 km
  • Harvey's Beach - 2 min drive - 2.5 km
  • Stay and Play LLC - 2 min drive - 2.5 km
  • Chalker Beach - 3 min drive - 2.5 km

Getting around

  • Old Saybrook Station - 6 min drive
  • New London, CT (GON-Groton - New London) - 30 min drive

Restaurants

  • ‪McDonald's - ‬3 min walk
  • ‪The Essex - ‬3 min drive
  • ‪Burger King - ‬2 min drive
  • ‪Starbucks - ‬2 min drive
  • ‪Dunkin' - ‬2 min drive

Frequently asked questions

Is Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats pet-friendly?

No, only service animals are welcome at the property.

How much is parking at Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats?

On-site parking is available at the property.

What time is check-in at Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats?

Check-in begins at 4:00 PM.

What time is check-out at Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats?

Checkout is at 11:00 AM.

Where is Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats located?

This family-friendly Old Saybrook holiday home is located by the sea, within 1 mi (2 km) of General William Hart House and Katharine Hepburn Cultural Arts Center. Saybrook Country Barn and Stay and Play LLC are also within 2 miles (3 km).

Reviews

9.8

Exceptional

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. 119 out of 136 reviews
Rating 8 - Good. 12 out of 136 reviews
Rating 6 - Okay. 1 out of 136 reviews
Rating 4 - Poor. 3 out of 136 reviews
Rating 2 - Terrible. 1 out of 136 reviews

9.6/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Hayley T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!
Stayed 3 nights in Jan 2026

10/10 Excellent

Karen B.

Liked: Cleanliness, communication, listing accuracy
This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening.
Stayed 2 nights in Dec 2025

10/10 Excellent

Todd R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very responsive. We had a sizable snow storm on our checkout morning and Yvette offered for us to checkout late. As well as giving us updates on the plow arrival.
Stayed 4 nights in Dec 2025

10/10 Excellent

Deana L.

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

Wonderful Stay

We loved our stay!
Stayed 2 nights in Dec 2024

10/10 Excellent

Rob C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back.
Stayed 1 night in Aug 2025

10/10 Excellent

Elyssa R.

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

Great time

Very much enjoyed our trip!
Stayed 1 night in Apr 2025

10/10 Excellent

Ray S.

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

Wonderful house

Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend.
Stayed 5 nights in Jun 2025

10/10 Excellent

ANN W.

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

Family weekend

The charming house was well furnished and well equipped. The host was responsive when there was a small issue about the backyard barbecue grill. We all enjoyed ourselves very much!
Stayed 4 nights in Jul 2025

10/10 Excellent

Shari M.

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

Lovely old historic New England home

We thoroughly enjoyed our stay...the historic home was a perfect New England getaway for our group of women.
Stayed 2 nights in Nov 2024

10/10 Excellent

Susannah A.

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

Perfect family vacation!

We absolutely loved this property. It was homey, charming, well stocked, and close to everything.
Stayed 8 nights in Aug 2024

10/10 Excellent

Nancy P.

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

Lovely taste of historic area

charming historic property, ideal for large groups.
Stayed 2 nights in Sep 2023

10/10 Excellent

Karen H.

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

Reunion of friends

We were a group of women who needed a place to gather. This house is a wonderful house. Full of beautiful art and plants. The side porch off the living room is a fabulous place to sit in the morning. Just a great place.
The porch/sun room where we gathered.
Another of the porch/sunroom.
Stayed 1 night in May 2025

10/10 Excellent

Michele L.

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

Great girls trip!

We had a nice time in this lovely home! Nice location, plenty of beds, and great communication from the host!
Stayed 1 night in Jul 2024

10/10 Excellent

Alma M.

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

Beautiful historic home

Charming place to stay and experience New England living. A comfortable place to stay with family. It has everything you need.
Stayed 4 nights in Jul 2024

10/10 Excellent

Jim K.

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

It's a great old house with lots of character!

We enjoyed the house and the grounds - the house was reportedly built in the late 1700's and has lots of character
Stayed 2 nights in Sep 2024

10/10 Excellent

Erin M.

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

Very clean! Great location.

We loved this house. So clean and great location.
Stayed 2 nights in Feb 2023

8/10 Good

Melissa H.

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

Fall Friends Weekend

Perfect for our fall weekend trip in Connecticut
Stayed 1 night in Nov 2024

10/10 Excellent

Mark F.

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

Charm of a historic home

This house is a reflection of the deep and impressive history of the property. There is a variety of art and artistic styles throughout to enjoy. A perfect place for a larger group and many local amenities nearby.
Stayed 2 nights in Nov 2024

10/10 Excellent

Denise L.

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

Company Retreat!

Awesome experience!
Stayed 1 night in Jun 2024

10/10 Excellent

Andrew B.

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

Great Property

Great property with an amazing outdoor space! Yvette was very kind and incredibly easy to work with.
Stayed 3 nights in May 2024

10/10 Excellent

Robert M.

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

Great stay that felt like home

My family and I were in town for a wedding and this place accommodated us all perfectly. Clean, plenty of rooms, and lots of character. The private backyard was great for hanging out. We all enjoyed our time here!
Stayed 2 nights in Sep 2022

10/10 Excellent

Anne D.

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

Family reunion

The house and property were very nice. We had ample room for everyone to eat together, and also had enough space so everyone had privacy. Lots of towels,beds were comfy and great location to town and beaches!
Stayed 7 nights in Aug 2023
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Julie N., Winchester

Great New England Getaway

Loved this house--great for a large group. It was extremelly well-maintained and the landlord was fabulous! The common area was very well-appointed and had a wonderful fireplace. Perfect for any size group...Thumbs up!

10/10 Excellent

Tricia L., Washington, DC, USA

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

Wonderful gathering spot

The house is so charming and has everything you could need for a wonderful getaway. We enjoyed the fire pit and the yard. The living room and dining room were great for gathering. The beds were comfortable. Overall, a terrific place.
Stayed 2 nights in Dec 2022

10/10 Excellent

Hadasi B.

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

Magical family time

The house was great, comfy beds, cute decor, had everything we needed - towels, blankets, utensils, enough rooms for quiet time and a huge living room for games and fun!
Stayed 3 nights in Jul 2023

About the host

Hosted by Yvette

Host profile image

Why they chose this property

The neighborhood here feels very much like classic Old Saybrook—quiet, lived-in, and comfortably local. Within about a half mile you’ll notice a mix of long-time residents, retirees, and families, with people out walking dogs, heading to coffee, or meeting friends downtown. Main Street Old Saybrook is close by with small shops, Paperback Café, ice cream spots, and casual restaurants, plus The Kate for shows and events. The area is generally safe and relaxed, especially in the evenings, though you’ll notice some daytime traffic as this part of town connects people to beaches, the train station, and nearby villages. It’s not flashy or touristy—more of a real coastal town where things move at a steady pace and neighbors know their routines.

What makes this property unique

✓ Authentic 1795 historic estate with charm and quirks
✓ Private grounds, porches, firepit for gatherings
✓ Well-stocked kitchen, books, fireside spaces

Premier Host

They consistently provide great experiences for their guests
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