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Orient Village — Historic Bayfront Cottage — 2025 Season

Photo gallery for Orient Village — Historic Bayfront Cottage — 2025 Season

Bayside Cottage, Orient
Bayside Cottage — the lawn, the buffer, the bay
Bayside Cottage — covered porch
Bayside Cottage — bay front porch and balcony
Bayside Cottage — bayfront balcony, off of themaster bedroom

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • On beach
  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Rooms & beds

3 bedrooms (sleeps 6)

Back

2 Single Beds

Bayfront master bedroom

1 Queen Bed

Bayview

2 Single Beds

2 bathrooms

Downstairs

Toilet · Shower only

Upstairs

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden

About this property

Orient Village — Historic Bayfront Cottage — 2025 Season

BAYSIDE COTTAGE is available from 3 April 2026. Minimum rental period is two weeks, which can be split over two stays. Discounts available for monthly and longer rental periods.

The Real Thing... the lull of lapping waves, private beach, on the Bay... Simple, plain, authentic, uncorrupted and unadorned “Summer of ‘42” beach cottage for those discerning few who recognize and appreciate the difference. Located in Orient’s National Historic District, and formerly part of Bay House Cottages. Adjacent to Orient Yacht Club. 2-minute walk to Orient Village and Oysterponds Historical Society. Deep-draft boat mooring available.

Upstairs: 3 Bedrooms, Bathroom, Bayfront Balcony
Downstairs: Parlor (w/Franklin Stove as heat source), Kitchen, Bathroom

Inside: Simple, Plain, Authentic & Uncorrupted
Outside: Covered Porch, Shower, Picket-fenced yard, WW1 Monument

Photos provide views of exterior and surroundings of Bayside Cottage, as well as an interior “walk through” and some items from the historical archives.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 9 kg per pet (limit one pet total)
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Smoking

Smoking is not permitted
Pets may be a much loved member of your family; however, they are allowed only after discussion, review and approval by the owner.

Important information

You need to know

Property Registration Number 1296
Property # 4965559
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

About the area

Orient

Located in Orient, this cottage is on the beach. Island's End Golf and Country Club and Kontokosta Winery are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Norman E. Klipp Marine Park and Greenport Carousel. East End Seaport Maritime Museum and Railroad Museum of Long Island are also worth visiting. Spend some time exploring the area's activities, including birdwatching, wildlife walks and winery tours.
View more Cottages in OrientOpens in a new window
Map
Orient, NY

What's nearby

  • Oysterponds Historical Society - 3 min walk - 0.3 km
  • Truman's Beach - 3 min drive - 2.5 km
  • Splish Splash Water Park - 51 min drive - 57.1 km
  • The Hamptons Beaches - 56 min drive - 67.2 km
  • Shinnecock Hills Golf Course - 62 min drive - 73.5 km

Getting around

  • Greenport Station - 14 min drive
  • East Hampton, NY (HTO) - 73 min drive

Restaurants

  • ‪First And South - ‬9 min drive
  • ‪Greenport Harbor Brewing Company - ‬9 min drive
  • ‪Green Hill Kitchen - ‬10 min drive
  • ‪1943 Pizza Bar - ‬9 min drive
  • ‪Aldo's - ‬10 min drive

Frequently asked questions

Is Orient Village — Historic Bayfront Cottage — 2025 Season pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

How much is parking at Orient Village — Historic Bayfront Cottage — 2025 Season?

On-site parking is available at the property.

What time is check-in at Orient Village — Historic Bayfront Cottage — 2025 Season?

Check-in begins at 4:00 PM.

What time is check-out at Orient Village — Historic Bayfront Cottage — 2025 Season?

Checkout is at 11:00 AM.

Where is Orient Village — Historic Bayfront Cottage — 2025 Season located?

Nestled on the beach, this Orient cottage is steps from Oysterponds Historical Society and 1.5 mi (2.4 km) from Truman's Beach. Norman E. Klipp Marine Park and 67 Steps Beach are also within 6 miles (10 km).

Reviews

10

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. 22 out of 24 reviews
Rating 8 - Good. 2 out of 24 reviews
Rating 6 - Okay. 0 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Tonia G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host is fantastic. The location would be ideal in the summer.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

William W.

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

Lovely spot

Beautiful place with great views and a private beach! Great food and nature nearby, and very accommodating host!
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Jon B.

Great little get away. Cute older beach cottage. The owner was awesome.

My family and 4 freinds all had a great time exploring and golfing some very nice golf courses in the area! Great place to stay no complaints at all!
Stayed 3 nights in Aug 2018
Verified

10/10 Excellent

Bruce K.

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

Fall 2024

We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!
Stayed 6 nights in Sep 2024
Verified

10/10 Excellent

Sally L. B.

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

Those sunsets

You don't go to this house for the latest in home decor. You go for the beauty of the place. Drinking coffee and staring at the water. Swimming in the water and then drinking wine and staring at the water. A place I know very well and a pleasure to be back. It helps a lot that Tim is right across the street and always happy to answer a question. A very relaxed, welcoming host
Stayed 7 nights in Sep 2022
Response from VrboOwner on 19 Sept, 2022
Thank you for capturing the nature and spirit of Bayside Cottage. It’s not for everyone; you passed the test and “got it”. Come again!
Verified

10/10 Excellent

Adrienne B.

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

Vintage cottage

The property’s greatest asset is its location. The cottage itself is in no way luxurious, and it all fairness it is not advertised as such. It is definitely a step back in time. A “Summer if 42” is an excellent description of the property. Would I go back? No. Am I glad I went? Yes! Vacations are about experiencing new things and sometimes those things are old. Orient Village is a great little town, a gem. If you want to feel more like part of the scene and not a tourist, this is a great place to stay.
Stayed 7 nights in Sep 2021
Response from VrboOwner on 12 Oct, 2021
Thank you for enjoying and appreciating the vintage and original quality of Bayside Cottage. Your review is entirely accurate and directly on point! Our current age is one of “faux” luxury when measured against the more authentic and unadorned standards of simpler times. I’m glad you experienced it and got it!
Verified

10/10 Excellent

Jennifer G.

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

Lovely Stay!

Step away from your busy schedule, step back in time, and step down to the beach. Bayside Cottage is an idyllic, charming, and rare place -- one increasingly harder to find as grandiose properties populate many parts of the Island. Thankfully the North Fork has retained much of its character since we began visiting some 20 years ago, and Orient is beautifully preserved with a lot of tender loving care, especially towards nature. It was turtle season in June! At Bayside, circa 1887, one doesn't need chic and glamor to enjoy the beautiful bay view, sailboats, rose bushes and occasional bunny, just a good book with afternoon tea or a glass of wine on the balcony, to the tune of lapping waves and mockingbirds. The bend where the picket-fenced, gray-shingled house sits could have been drawn from Harper Lee, but furnishings tell another story -- pictures of sailors, rowers, boats, shells, maps, needlepoints, even old tools -- thoughtfully collected over time. The main dock and marina are right next door, and you will observe a few apprentice sailors as lessons are available.This lovely cottage is situated in an historic and peaceful hamlet, complete with a general store, post office, and small cafe. The cottage is delightfully old and comfortable, and perfect for relaxing, enjoying simplicity and family time. Nicely there is no TV, but there are board games and wifi -- and your most gracious, welcoming, and attentive host is but a stone's throw away.Thank you for having us!
Stayed 7 nights in Jun 2025
Response from VrboOwner on 3 Jul, 2025
Many thanks for both your stay, and your gracious and thoughtful review of Bayside Cottage and its simpler and lost sensibilities. Openly available to all, truly appreciated only by the increasingly rare and discerning few. I am glad you stepped back and found it, and that it found and spoke to you. Step back and come again. Best and be well.
Verified

10/10 Excellent

Joanie G.

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

Family Vacation

Three generations of our family couldn't have asked for a better cottage by the water. Sunsets incomparable, neighborhood friendly, ice cream perfect. We will be back. Thank you for welcoming us. Joanie and Mark
Stayed 14 nights in Aug 2022
Verified

10/10 Excellent

Terry B.

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

A little slice of heaven

The Bayside cottage is the quintessential beach cottage. If you're looking for a luxurious fully equipped house this place is not for you. If you're looking for a gorgeous view of the sunset walk out your door to the beach, this is the place for you. This is a rustic style cottage 15 paces from the beach. See the sunset every night from the porch and from the master balcony or the beach.Walk to the ice cream store or the general store. Bike through the neighborhood, or just sit on the porch and stare at the water.
Stayed 7 nights in Jun 2022
Verified

8/10 Good

Dawn K.

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

Bayside Cottage Fall Getaway

the location on the bay and town of Orient was excellent. The weather was great, but when the wind a couple nights got cold without heat but a fire made it cozy. The home has everything we needed with great views, towels, bedding, kitchenware and walking access to the market and 2 small take out restaurants. Overall a great place.
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

Simon H.

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

Very Special Home

Great host, could not ask for a better location, view, charm and experience. Thank you!!
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

haley p.

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

Amazing time!!!

We had such a wonderful, relaxing time at the Bayhouse. Not only was the town so beautiful but the view from the house was perfect. Hearing the waves at night as I fell asleep was magic! The house itself was great - clean, charming and had everything we needed. Tim was an excellent host - quick to respond and so friendly. We wish we could have stayed all summer!!! We hope to be back someday to enjoy the serenity of the Bayhouse.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Sandy P.

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

Perfect location, breeze, and views

This cottage is such a peaceful getaway with the sound of the water lapping on the shore and beautiful views every way you look. It's a rustic but well maintained cottage on your own private beach, with the very responsive host right across the street in case you have any questions. We rented bikes for the week from Dan's Bike Rental and they drop off and pick up the bikes whenever you want. I highly recommend this; it's the best way to check out all the beautiful scenery and beaches that Orient has to offer. The kitchen is small but well equipped with everything you'd need to cook and serve any meal. There is also a small grill outside. The master bedroom was our favorite spot in the house. The bed faces the balcony overlooking the beach, so get ready to be lulled to sleep with the lovely breeze and beach sounds.
Stayed 6 nights in Jun 2021
Verified

10/10 Excellent

Philip C.

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

The perfect spring getaway

My wife, our friends and I had a really wonderful time at the bayside cottage. It was the perfect escape from the city—quiet, pleasant, peaceful. Tim was very kind and easy to communicate with. Though the weather in April was surprisingly nice, the wood stove was appreciated for the cooler mornings and evenings. Some of the furniture and decor is a bit older and worn, but for me that was part of the comfortable charm. I am hoping we can return again soon.
Stayed 7 nights in Apr 2021
Verified

10/10 Excellent

Susan M.

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

Marvelous

The location of this modest cottage directly on the bay is spectacular- with breathtaking sunsets. Its an outside place with a huge covered porch - The town is simple and lovely. Owner of the property is always accommodating and quick to respond. The interior is very basic with everything you need in the kitchen and good beds and linens.
Stayed 14 nights in Sep 2020
Verified

10/10 Excellent

wesley t.

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

Just what the doctor ordered: A relaxing change of scenery for telework!

Tim is a great host and very close to the rental cottage for easy communication and a warm welcome. The house was built in 1887 so your expectations must be adjusted for the reality of some minor limitations (bathrooms were dated, but there were TWO!!!). We don't look for luxe accommodations, so it suited our tastes well. If you want sleek and new, look elsewhere. That is not a knock, just preference. Orient is all about old beachtown charm. We didn't have many needs besides beds, wifi, and access to the beach. We got that plus the charm of a nice home, and the best bay view. I don't think I've ever woken up to the sound of waves, even in my travels to tropical places. The weather was just right to leave the doors open at night and enjoy the air. (there is A/C if you need it). My recommendation for families is that if you are going to stay for more than a day or two, bring your own kitchen spices etc to cook with. There are the essentials (plates, coffee maker/grinder, large fridge/freezer), but bring anything else you need beyond salt and pepper. I like to cook a lot so it wasn't a problem to run to the IGA 15 minutes away and get whatever I needed. I used the grill a lot and also the stove. Tim was wonderful to chat with and we hope to be back next year.
Stayed 4 nights in Aug 2020
Verified

10/10 Excellent

Melissa S.

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

Lovely home, great location.

Exactly what I was looking for in a beach cottage. Can’t wait to return.
Stayed 12 nights in Jun 2020
Verified

10/10 Excellent

Gerald M.

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

Bayhouse

Semi rustic, cottage with historic roots. Provides excellent water scenery, pleasant breeze with that classic, open water smell.
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Colin M.

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

Perfect summer spot...

This cottage was perfect for our small group (two couples and one toddler). The location can’t be improved upon, and the cottage was as charming as possible. Bring sunscreen because if the weather is even halfway decent you’re going to want to be outside most of the time, enjoying the view....
Stayed 4 nights in May 2019
Verified

10/10 Excellent

Harvey F.

Beautiful getaway for your busy life

Five of our family stayed here for most of a week in mid-springtime. If you are familiar with the Long Island Southold, Greenport Harbor area, you know that Orient is close by these but in a quieter area nearer the end of the North Fork. This gives it a very nice balance of peace and calm and with easy access to things to do. When we were at the cottage, we enjoyed the bay view and breeze, sounds of waves and birds and some glorious sunsets from the porch. Osprey where frequent flyers by the bay. Bayside Cottage is on the beach and has no immediate neighbor house on one side, helps with the feeling of a place just for you. A short walk down the street brings you to the Orient Country Store for easy breakfast or tasty lunch sandwiches and salads. Don't miss some of their selection of house made cookies for desert. We enjoyed the attractions of the area for oysters (Little Creek Oyster Farm); clams, fresh fish, oysters and IGA bought onion rolls filled seafood salad (shrimp-crab-lobster) from Southold Seafood Market, good times beer and food at Greenport Harbor Brewery (Southold), and tastings at a select few of the many excellent local wineries. Nearby nature preserves we visited included Orient Point State Park and Mashomack Preserve. The latter features a system of trials with viewing of wildlife and local flora (labelled for your interest). Tim, our host, was very helpful and likeable, easily accessible whenever we needed something, more of a friend than a host in the way we were treated. I'd like to go back to Bayside Cottage for my next visit to the North Fork area just to see the sunsets again.
Stayed 7 nights in May 2019
Response from VrboOwner on 1 Apr, 2020
Many thanks for your gracious and generous review. Sounds like you took in the relaxing throw-back charm and vibe of Bayside Cottage and Orient while still undertaking a full slate of local activities. Enjoyed hosting you, and, when you get the urge and need, feel free to wander on back. Until then, God bless Texas!
Verified

10/10 Excellent

ted k.

Wonderful getaway

We had a great time in this charming cottage. The owner was so unbelievably accommodating! Beautiful location!
Stayed 4 nights in Oct 2018
Verified

10/10 Excellent

Liz & paul M.

beachy

It had a very beachy feel. Not luxury but comfortable. It was right on the water with a beautiful deck at the side of the house. Plenty of chairs to sit and enjoy the view. The bedrooms were roomy enough. The bathrooms could stand an upgrade but they were clean.
Stayed 4 nights in Oct 2018
Verified

10/10 Excellent

Joanne G.

Great Place!

We loved Bayside Cottage, we came here for a weekend fishing trip for my husbands birthday and had a great time. Wood burner was a plus!. Owner was very nice and accommodating also. We cant wait to come back to Orient.
Stayed 2 nights in Sep 2018
Verified

8/10 Good

Diane C.

Stayed 30 nights in Jul 2025

About the host

Hosted by Tim Frost

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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