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Spectacular Waterfront home on Southold bay - one of a kind!

19 Reviews
Bedrooms 4
Property type house
Minimum Stay 7 nights

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Minimum Stay
7 nights


Southold House Rental Photos and Description

4 Bedrooms, 2 full baths, sleeps 10

Located in the private beach community of Reydon Shores, 'The Roost' was newly built in 2007-2008. This property is bordered by over 400 acres of forever wild land which abounds with astounding wildlife and rare birds. It boasts a 140 degree water view of Southold bay with huge glass windows on three sides to optimize the views. Off the Master Bedroom is a cozy sky deck perfect for sunrises and spectacular sights of the east ends continuous show of Yachts & Tall Ships. Also located upstairs are two additional bedrooms with queen beds. Downstairs has a spacious laundry closet, another bedroom with a full bath. The Kitchen, dining and living room are a combined 'Huge great room' with incredible water views with endless glass windows and doors. The living room has a 50 inch HD flat screen, wireless Internet and stereo.


Fishing Charters : 1-FISHING TRIPS; Specializing in teaching children (and adults) the art of fishing. Our waters hold many species of different fish from prime fluke, scup, sea trout, striped bass, bluefish, blackfish, flounder, tuna and shark. Capt'n Roo is one of the best fisherman on the north fork and loves to share his fishing skills with his quests. Capt'n Roo has the patience and knowledge to make sure the kids (and adults) have an unforgettable fishing experience. We supply the bait, tackle, boat ( 25ft center console inboard) and tales for a great time. All you need is sunscreen, drinks, lunch and towels just in case you might want a quick swim. At the end of the trip- all your fish will be cleaned and properly packaged- ready to eat.

Boating adventure tours: 2- ADVENTURE TOURS;

Your family can choose from swimming, clamming, snorkeling, fishing, and sightseeing .You choose the adventure and set out for a 2 ,4 or 6 hr. trip . For example our most popular trip is the 6 hr. excursion too Southampton Ocean beach. The day begins ( with 15 minute safety briefing and rules set by the captain.) at 9:45 am. We Load the boat (docked on site) with beach gear and were off with a full hour of boating thru the great peconic bay , going thru the Shinnecock Canal and crossing the great Shinnecock Bay where we beach the boat on bayside where you have a short walk over the dunes to one of the most spectacular Ocean Beaches on the east coast. There our quests can choose to remain on the beach (for apprx. 3 hrs) or continue thru the shinnecock inlet for some exciting offshore fishing for the prized doormat fluke and Striped Bass.At apprx. 2:30pm we pick up the beachers and head back towards the northfork. We arrive back at the dock at appr. 4:oopm

Clam Bakes * Cookouts * Barbeques:

Cap'tn Roo is a retired professional caterer specializing in outdoor catering. So kick back settle in with the sights while your clambake is prepared and served on site.

Note: All Fishing ,Cruises, Adventure Trips and Catering are subject to weather and tides so planning events need flexibility.

Prices for all activities given upon request.

More Details
  • non smoking only
  • pets not allowed
  • unsuitable for elderly or infirm
  • wheelchair inaccessible

Chuck Hill
Member since: 2010
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
August 3, 2016
Call Owner

Guestbook comments from the owner

"Truly a piece of heaven! Chuck is the friendliest owner and the house is majestic! I've rented many places over a decade and this house, owner and little touches stand far above the rest!

Thank you Chuck- we will be back soon!

Irene I.
Apr 2010
  • 1 of 6


based on 19 traveler reviews

Spectacular Waterfront home on Southold bay - one of a kind!
average rating of 5.0 based on 25 reviews

Beautiful Home in Southold

  • 5 of 5

Chuck was WONDERFUL to work with, very responsive, very flexible. The house was beautiful, very clean and very modern. The beds were very comfortable, the kitchen was well stocked, the view of the bay was beautiful. Chuck was always a phone call away if we had any questions or problems. He recommended some restaurants, but unfortunately many were closed due to our scheduled visit (12/30/15-1/1/16). We enjoyed visiting a couple of wineries one day and the Greenport Harbor Brewery the following day. The house is on a dead end, so there was no traffic, very quiet neighborhood. I’ve stayed in many VRBO homes, and this was our favorite. We look forward to renting again. Thanks Chuck!

  • Submitted: Jan 12, 2016
  • Stayed: Dec 2015
  • Source: VRBO, from HomeAway
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Bayside, Queens


  • 5 of 5

Stayed here with my family from Friday afternoon till Monday afternoon as I was getting married at Raphael vineyards that Saturday. House and surrounding property are amazing. Postcard views from all levels, including a 2nd floor master with a terrace that overlooks the bay. Chuck is warm, welcoming (bottle of wine and welcome basket) and extremely accommodating. Allowed us full use of the property, even his kayaks! Very secluded location, away from any crowds or noise makes this place a must stay. Definitely plan to be back!

  • Submitted: Jun 16, 2015
  • Stayed: Jun 2015
  • Source: VRBO, from HomeAway
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Lovely House

  • 5 of 5

5 of us make friends stayed here and used it as a base for golf. Beautiful house and location and Chuck was extremely helpful and welcoming. We hope to go back.

  • Submitted: Aug 21, 2014
  • Stayed: Jul 2014
  • Source: HomeAway
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Exquisite getaway retreat!

  • 5 of 5

From the moment we entered the house and met Chuck, we were hooked! The home is beautiful and welcoming. The open layout and the view of the Bay is just stunning. The amenities are tremendous. The home is located in a quiet, secluded area overlooking the gorgeous Bay. All the windows allow nature to come in and brighten your day. The home was spotless and very well maintained. We were there for a family wedding, and wish we had more time to spend at the house relaxing. There are so many great restaurants and shops to visit, but you really just want to spend your time at the house enjoying the view and the beauty of the area. We will most definitely be back! Thank you Chuck and Lynn for renting out your little piece of heaven!!!

  • Submitted: May 20, 2014
  • Stayed: May 2014
  • Source: HomeAway
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A Little Bit of Heaven...hidden in Southold !

  • 5 of 5

We have been going away on a family vacation every summer for 30 years and our stay at The Roost" was by far the best! The house is beautiful, and has every amenity imaginable. It was close to the wineries and Greenport village. Chuck was a perfect host... even brought us sunflowers and a delicious strawberry pie! The view is spectacular ... i miss it already. Can't wait to go back again next summer!

  • Submitted: Jul 22, 2013
  • Stayed: Jul 2013
  • Source: HomeAway
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Forest Hills, New York

GREAT home!

  • 5 of 5

What a lovely home!

A few girls got together for a weekend of relaxation and wine tasting... this was the perfect home!

Gorgeous in every way... clean... updated... comfortable.

This home is a must!

I will be staying here again and again and again.

Thank you Chuck!

  • Submitted: Sep 17, 2012
  • Stayed: Sep 2012
  • Source: HomeAway
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Nearest Airport
40 Miles
Nearest Barpub
3 Miles
Founders Landing
Nearest Ferry
7 Miles
Nearest Golf
7 Miles
Island Links
Nearest Train
3 Miles
Nearest Motorway
20 Miles
Nearest Restaurant
3 Miles
Founders Landing
Car: recommended

We are located on the north shore of Hogs neck in Southold. This area is very special as it is very quiet, serene and mostly still exists in its wild state. It is home to Cedar Beach, Goose creek, Paradise point and three prominent wineries. The Indian Museum and Custer Telescope ( famous for study of the solar system) make their home here as well. The North Fork Triathalon is held here every year in the beginning of July mainly due to the extreme low volume of traffic. Horses, pony drawn buggys, runners , Bicyclists and walkers feel they have the roads to themselves.


Rates & Availability

Southold House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate
7 night minimum stay

Additional information about rental rates

Property Damage Protection $59
Refundable damage deposit $300
Cleaning $135

The above rates are for a six person rental- Please note that larger parties are subject to a surcharge based on the number of guests. We normally charge $50-$75 per person over 6 with a max at 10.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
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Southold House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 2500 sq. ft.
Location Type:
  • Beach
  • Waterfront
  • Adventure
  • Away From It All
  • Activities Guide
  • Air Conditioning
  • Ceiling Fans
  • Clothes Dryer
  • Filtered Water
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • 4 Ring Stove
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Lobster Pot
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , tub , shower
    Bathroom 2 - toilet , shower
    Bathroom 3 - outdoor shower
  • 4 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 king , Plus Bunkbeds in adjacent room /closet
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 queen
    Bedroom 4 - 1 twin/ single , bunkbeds
  • Master Bedroom is huge with a pillow topped custom mattress that makes sleeping an incredible experience. Off the bedroom is a sky deck boasting the best water view southold has to offer. This is a great way to greet the day at sunrise watching ospreys catch fish, Yachts and Tall Ships cruising by and local fisherman tending their catch. Additionally there is a walk in closet with a set of bunkbeds for extra sleeping and a beautiful master bath with a clawfoot soaking tub as well as a spacious shower equipped with a rain showerhead.
  • Books
  • CD Player
  • DVD Player
  • Radio
  • Satellite / Cable
  • Stereo
  • Television
  • Balcony
  • Barbecue
  • Boat Dock
  • Deck / Patio
  • Fish Cleaning Table
  • Lawn / Garden
  • Outdoor Grill
  • Outdoor Grill Gas
  • Patio
  • Porch / Veranda
  • Unscreened Porch / Veranda
  • 8 garden chairs
  • 4 beach chairs
  • non smoking only
  • pets not allowed
  • unsuitable for elderly or infirm
  • wheelchair inaccessible
  • autumn foliage
  • bay/sound
  • churches
  • cinemas
  • forests
  • library
  • marina
  • museums
  • playground
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • horseback riding
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • swimming
  • tennis
  • water skiing
  • wind-surfing
SUNSET CRUISES and water taxi service to and from; Greenport, Shelter Island, & Sag Harbor for Shopping, Dining and activities. An example would be an afternoon cocktail cruise leaving the dock Late afternoon- (your choice of time).We arrive at a destination of your choice such as Sag Harbor where we drop you off at the Town Dock for an evening in town. Pickup time is at your discretion but curfew is 11:00pm. Prices upon request.

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