Entire home

Spacious Southampton Waterview

Bayside holiday home with kitchen and balcony

Rear Patio with BBQ grill, lounges and table

Overview
Amenities
Policies
Location

Wonderful

5 bedrooms5+ bathroomsSleeps 104500 sq ft

Popular amenities

Parking available
Pet-friendly
Dryer
Washer
Fireplace

Explore the area

Southampton, NY

Place, The Hamptons Beaches
‪3 min drive‬
Place, Shinnecock Hills Golf Course
‪4 min drive‬
Place, Cooper's Beach
‪12 min drive‬
Airport, Westhampton, NY (FOK-Francis S. Gabreski)
‪16 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Single Bed

Bedroom 4

1 Single Bed, 1 Double Bed and 1 Queen Bed

Bedroom 5

1 Double Bed

5 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Bathtub or shower · Toilet

Bathroom 4

Toilet

Bathroom 5

Bathtub · Toilet

Bathroom 6

Soap · Bathtub or shower · Toilet

Spaces

Deck or patio

Porch or lanai

Kitchen

Kitchenette

Balcony

Separate dining area

Outdoor play area

Garden

About this property

Spacious Southampton Waterview

"Spacious charm" suggests the delights of this unique, roomy (4,000 sf, 5BR/5.5 bath), historic “Shingle Style” hillside home on 3.7 acres, with spectacular views of Shinnecock Bay (a safe 2-minute walk to beach). All bathrooms have been recently renovated, and there is a new cook’s kitchen, paneled Living Room w/fireplace and grand piano, TV/rec room (HD cable and wireless internet included), two Bay-view verandas for dining or cocktails, A/C in all bedrooms, ample outdoor lawns for relaxation or play, and a lovely sheltered brick patio for sunning and barbecues. A firepit with picnic table and rustic benches off the back lawn is a favorite with our guests for roasting marshmallows and just hanging out with friends.
Children love the rambling spaces and seemingly endless nooks and crannies of the house. Perfect for entertaining your weekend guests, yet with no lack of charming “hideaways” for those who’d prefer to escape to a quiet corner for a while.
Must be seen to be appreciated. No shared rentals, please.

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Amenities

Kitchen

Washing machine

Dryer

Pet-friendly

Free WiFi

Air conditioning

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House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 12:00 PM

Children

Children allowed: ages 13–17

Events

No events allowed

Pets

Pets allowed: dogs and cats (limit 1 total)

Requires Owner's permission. $50 surcharge.

Smoking

Smoking is not permitted

Non-smoking rule strictly enforced

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

On-site parties or group events are strictly prohibited

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

We should mention

A car is required for transport to and from this property

About the area

Southampton

Located in Southampton, this holiday home is near theme parks and near the beach. North Main Street Historic District and Halsey House are local landmarks, and some of the area's attractions include South Fork Natural History Museum and Nature Center and Children's Museum of The East End. Travelling with kids? Consider All Star Bowling and Safari Adventure. Jet skiing and waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.

View more Holiday homes in Southampton

Southampton, NY

What's nearby

The Hamptons Beaches - 3 min drive - 2.1 km
Shinnecock Hills Golf Course - 4 min drive - 4.3 km
Shinnecock Nation Cultural Center and Museum - 5 min drive - 4.3 km
Cooper's Beach - 12 min drive - 8.1 km
Ponquogue Beach - 14 min drive - 13.3 km

Getting around

Hampton Bays Station - 9 min drive
Westhampton, NY (FOK-Francis S. Gabreski) - 19 min drive

Restaurants

‪Rumba - ‬4 min drive
‪Cowfish - ‬4 min drive
‪Canal Cafe - ‬4 min drive
‪Shinnecock Lobster Factory - ‬4 min drive
‪Good Ground Tavern - ‬3 min drive

Frequently asked questions

Is Spacious Southampton Waterview pet-friendly?

Yes, this property allows cats and dogs (limit 1 total).

What time is check-in at Spacious Southampton Waterview?

Check-in begins at 3:00 PM.

What time is check-out at Spacious Southampton Waterview?

Checkout is at 12:00 PM.

Where is Spacious Southampton Waterview located?

This family-friendly Southampton holiday home is located by the sea, within 3 mi (5 km) of Meschutt Beach, Shinnecock Hills Golf Course and Shinnecock Nation Cultural Center and Museum. Cooper's Beach and Good Ground Park are also within 6 miles (10 km).

9.0

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

8.2/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.6/10

Location

9.0/10

Listing accuracy

10/10 Excellent

Zhenya N.

1 Jul, 2024

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

Great weekend in Southampton!

My friends and I booked Mr. Freeman's place for a weekend get together, and loved every minute of it. The house is spacious, with lots of history baked into every corner and picture on the wall. It was a short drive from the beach, and in a nice, quiet location. We enjoyed our stay and would highly recommend this place to everyone!

Stayed 3 nights in Jun 2024

10/10 Excellent

Blair C.

12 Sept, 2023

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

Just what we imagined

I was looking for a unique, comfortable home for a girls trip to the Hamptons, and this property blew me away! It's very very large and we did not feel cramped at all even with 9 adults. Despite the home's age, the air conditioning worked beautifully. It is such a unique, lovable home and we enjoyed noticing a new piece of artwork or detail every time we entered a room. Very pleased with our stay.

Stayed 3 nights in Sep 2023

8/10 Good

Maureen S.

8 Jul, 2022

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

Large old home on secluded property

Beautiful 100+ year old home on large secluded property. Perfect for large family gathering. Many sitting areas inside and outside. Overall great. A couple room a/c units need replacing. Beware, lots of ticks outside.

Stayed 5 nights in Jun 2022

This review was submitted before 2018 and has not been verified.

10/10 Excellent

Jessica B.

10 Aug, 2011

Great Family Getaway

Our family loved spending a week at this huge historic house. The house had lots of interesting architectural features, lovely outdoor spaces, and a fire pit for roasting marshmallows. The house was very clean with modern bathrooms and kitchen appliances. The description provided in the listing is right on. We loved spending time on the balconies enjoying the bay view and bird watching. It was very relaxing and was only a short drive to Southampton and Hampton Bay beaches. Good access to cycling routes. The owners were genuinely nice and very helpful. I would definitely recommend it for a family vacation or romantic getaway.

8/10 Good

Steven C.

18 Aug, 2024

Liked: Check-in, communication, location

Disliked: Listing accuracy

Wedding weekend

Huge old estate built in the early 1900s. Everything works but needs updating. Tons of antiques makes it challenging for young children. The amenities stated hot tub / spa but none ever existed on premises. The host was very prompt with responses to questions. The refrigerator and freezer had items for owner that were off limits and especially in refrigerator took up lots of space. The Hamptons are expensive so this is a good place to stay if you are on a budget and don’t mind musty smells and lots of closets, cabinets off limits. Btw, lots of deer ticks around the property so be careful and check yourselves.

Stayed 5 nights in Aug 2024

10/10 Excellent

N Patrick H.

16 Sept, 2022

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

Sugarloaf

unique, captivating, obviously full of history

Stayed 3 nights in Sep 2022

10/10 Excellent

Darren S.

25 Aug, 2021

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

Perfect location

Plenty of space and amazing location.

Stayed 3 nights in Aug 2021

10/10 Excellent

Patricia L.

10 Aug, 2021

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

Our Stay at Sugarloaf

Our stay at Sugarloaf Cottage was great. The house looks exactly as advertised. It’s a very large house that’s over 100 years old but has all of the modern conveniences. My family and I loved the fire pit and we had our morning coffee everyday out on the veranda. The owner was very pleasant to work with. He responded almost immediately to all of my emails and made sure we were happy with house. I would definitely rent this house again.

Stayed 7 nights in Aug 2021

10/10 Excellent

JC d.

2 Aug, 2021

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

A very special, old, charming house

This house is very special – it has a long history and a tremendous amount of character. We very much enjoyed staying there for the whole month of July with our family. Our young girls loved its nooks and crannies (and the outdoor fire pit for making smores) and it was convenient to not only Shinnecock Bay, at walking distance, but also to the Atlantic Ocean beaches, with Cooper’s Beach about 10 mins by car. At times, the rooms on the top floor got hot but the AC (available in each bedroom) helped, and a new, large AC unit on the main floor was very effective. It is an old, charming house, well lived-in (with great shelves of books), well-equipped, which we found to be as advertised. We felt like it was a privilege to have the ability to experience this special place. We found the owners to be extremely responsive to any query we had and very helpful.

Stayed 28 nights in Jul 2021

10/10 Excellent

Ryan B., New York

17 Jun, 2020

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

Summer at the Sugarloaf

This place is awesome! Conveniently located to a bunch of great beaches, Southampton town and Hampton Bays town. The grounds of the property are perfect for lawn games, and the many decks are ideal for cocktail hour for the sunset! The house was clean and overall the trip was great. Communication with the host was also seamless.

Stayed 7 nights in Jun 2020

8/10 Good

Takami S.

28 Aug, 2019

Liked: Check-in, communication, location, listing accuracy

Our stay in the Southampton historical house

Overall, we enjoyed our stay in this house. This is more than 100 years old historical house and we understood that the atmosphere is quite different from staying in modern hotels or newly developed houses. First of all, there is no air conditioner in the house. It was a hot day when we arrived and the house was 92 F. It took several hours to feel comfortable in staying inside of house. The following days were cooler and we did not have such problem. The second thing is a room door knob. We were locked in the master bed room on the first floor and we needed to ask someone to open the door from the outside. It was as if the house was scaring us. Otherwise, it was enjoyable experience. Starry sky was incredible and we enjoyed watching deers passing by the yard. We appreciated the owner spent a lot of time to maintain this old house.

Stayed 3 nights in Aug 2019

6/10 Okay

veronica b.

22 Aug, 2019

Liked: Check-in, listing accuracy

Vacanza in famiglia

Tutto bene, struttura vecchia ma accogliente e spaziosa

Stayed 4 nights in Aug 2019

10/10 Excellent

Alexandra S., Flushing

24 Jul, 2019

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

A Gem in Hampton Bays

I rented this house for out of town family to stay in during our wedding weekend. We had so much fun exploring the property, and fire pit was a big hit. The grounds and views are beautiful. It is (as advertised) an old house, but if you like charm and character like we do, you will absolutely love this place. Thank you to the Freemans for providing our guests with your home for the weekend!

Stayed 3 nights in Jul 2019

4/10 Poor

Todd B., Chicago, IL USA

7 Jul, 2019

Liked: Check-in, communication

Disliked: Cleanliness, listing accuracy

Big & unique, but needs some TLC

Large, historic home, but in need of some significant updating and upkeep. Unfortunately in this old beauty, which is heavily wooded, we had to deal with subpar a/c & water pressure, insects, dust and animal smells. This could be a true gem in Southampton, but it needs some work.

Stayed 3 nights in Jun 2019

10/10 Excellent

mathini s., Bethesda MD

20 Jun, 2019

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

Very beautiful home

Very beautiful home and convenient to attractions and shopping.

This review was submitted before 2018 and has not been verified.

8/10 Good

Andrew H.

20 Aug, 2016

A vacation rental with character and charm

This Southampton vacation rental lived up to its billing and description, and was spacious enough for our family (retired couple, two adult children, son-in-law, and young grandson), family friends, as well as assorted visitors who came for a meal or a night or two. Wonderful spaces to entertain in (two verandas, patio, large lawn) as well as quiet places too, so we were definitely able to spread out, as well as to move about the house depending on whether we wanted sunshine or shade. We didn’t realize we’d booked a historic, architect-designed house (more than 100 years old!) or that some of the owners were artists, so that added to its quirky charm. Great location in The Hamptons (near both Hampton Bays and Southampton), close to beaches, and situated before the traffic gets really congested. There are plenty of interesting things to do in the area (art galleries, wineries to name a couple), but we also enjoyed just hanging out at the house, cooking, and sharing meals together. We spent a pleasant week here, the only downsides being the lack of a working washer and dryer and leaks in a bedroom during downpours (but fortunately, the leaks weren’t over the bed). We are West Coast folks and this was our first visit to Long Island, but if we came back to The Hamptons, we’d want to stay here again.

Stayed 7 nights in Jul 2016

This review was submitted before 2018 and has not been verified.

8/10 Good

Robert S., Williston Pk,NY

9 Sept, 2013

Perfect for large family

If you want to experience the Hamptons circa early 20th century with modern conveniences and you have a large family, this is the house for you. If you are interested in character and history, this is the house for you. It sits high on a hill at the end of a long driveway in a very private, quite and peaceful location overlooking Shinnecock Bay yet it is very convenient to Hampton Bays or Southampton as well as to several beaches and other areas of interest. Parking for multiple cars is more than adequate. All the rooms (there are a lot) are large and you can always find a quite spot in a house full of people. The house is reasonably priced for the Hamptons. All in all, my large family spent 2 wonderful weeks in this house and I would highly recommend it to anyone who is looking for tradition and not glitz.