Photo by Nina Dinoff

Holiday Homes in Greenport

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Holiday Homes in Greenport

Property grounds
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
8.0 out of 10, Very good, (1)
"The property was perfect for our needs! My husband was able to work from the desk in the primary bedroom during the day while my mom and I shopped and explored nearby! Our dog LOVED the backyard and space to explore. We didn’t even need to go venture to the nearby dog park, but that was also super close! As out of towners, unfamiliar with locale, we would recommend bottled water for drinking. Everywhere we went was 5-15 min drive, we very much enjoyed our stay and grateful for the opportunity to...
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Exterior
Enjoy the North Fork of Long Island at Our Lovely Home
Enjoy the North Fork of Long Island at Our Lovely Home
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is NZ$2,152
includes taxes & fees
9 Jun - 10 Jun
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Fridge, microwave, oven, stovetop
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
10.0 out of 10, Exceptional, (41)
"This home was immaculately clean, well decorated and well equipped. It had everything you need including toiletries (soap, shampoo, conditioner, etc). I would definitely recommend it."
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
Property grounds
Waterfront Beach House
9.6 out of 10, Exceptional, (33)
"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."
Waterfront Beach House
Property grounds
The SandPiper
9.4 out of 10, Exceptional, (3)
"This listing was exactly as described and was a great little apartment in Greenport with everything we needed. About a 10 minute walk to downtown area which was very convenient. It sits on a busy street so there is some noise from the road but it did not bother us too much and the host provided noise machines in the bedrooms which was very helpful. Overall I recommend this apartment and would definitely stay in the future!"
The SandPiper
Fridge, microwave, oven, stovetop
Beach Cottage, > .5 walk to beach, quaint, Beach community
10.0 out of 10, Exceptional, (1)
"Pretty gingerbread cottage, well appointed. Lovely area, 2 min walk to the beach. Owners super helpful. Overall beautiful, serene, highly recommmend."
The price is NZ$534
includes taxes & fees
29 May - 30 May
Beach Cottage, > .5 walk to beach, quaint, Beach community
Outdoor pool
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Interior
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, (1)
"I found it cozy, comfortable and very peaceful. Bonus wildlife visits of deer, geese and turkeys, Most people will understand this accommodation as quality “clamping”."
The price is NZ$388
includes taxes & fees
27 May - 28 May
Airstream Art Studio Sculpture/Nature Preserve
Fridge, microwave, stovetop, dishwasher
Remodeled Farmhouse in Waterford Near 2 Beaches!
10.0 out of 10, Exceptional, (60)
"Great stay, convenient location, very charming house with everything we needed."
Remodeled Farmhouse in Waterford Near 2 Beaches!
Fridge, microwave, oven, stovetop
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
10.0 out of 10, Exceptional, (21)
"Our group of four friends in our 50s loved our stay here. Heather was a responsive, welcoming, flexible host who left us a card, bottle of wine and a prepped wood pile in the fire pit. The decor was tasteful and beautiful, clean and modern. The mattresses were firm, which we liked. We made use of the comfortable couch on the deck as well as the gas fireplace in the living room. The location is lovely and we had a short, 5-minute walk to the beach. Birders would enjoy the tremendous diversity of...
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️
Property grounds
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
10.0 out of 10, Exceptional, (162)
"Got away for a girls weekend and this was perfect. It was close to wineries, and a short Uber away to Greenport. The house was comfortable, clean, and private with enough space for all 8 of us. The outside was also beautiful- right on the water. Highly recommend!!"
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
Pool
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, (10)
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
A heated pool
July month or weekly still available. Hampton 5br, pool, hot tub, private beach.
10.0 out of 10, Exceptional, (67)
"The house was great - just as listed and very comfortable / kid friendly. There wasn't a whole lot to do in the area over the holidays but we enjoyed the house, trampoline and jungle gym."
July month or weekly still available. Hampton 5br, pool, hot tub, private beach.
Property grounds
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
10.0 out of 10, Exceptional, (10)
"Perfect spot for a weekend on the North Fork"
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
Beach
The Hampton Sack a cheerful relaxing beach cottage
7.2 out of 10, Good, (11)
"Truly no frills but key things work like heat and internet. Quite small but OK for 2 people."
The Hampton Sack a cheerful relaxing beach cottage
Don't see what you're looking for?
See all available properties in Greenport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Greenport

Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is NZ$419
includes taxes & fees
29 May - 30 May
Cliffside Resort Condominiums
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$426
includes taxes & fees
28 May - 29 May
Windward Shores Ocean Resort
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (186)
"Well maintained upscale resort. "
The price is NZ$369
includes taxes & fees
9 Jun - 10 Jun
Driftwood Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Greenport Holiday Homes information

Number of reviews
523
Accommodation
1560 Holiday Homes
Lowest Price
NZ$388
Highest Price
NZ$2,152

Recent Reviews in Greenport
Expedia verified reviews

The Niantic Inn

The Niantic Inn

5/5 Excellent
Excellent hotel!
"Our experience in Niantic and at the Niantic Inn was great! The owner was very friendly and helpful. There was EVERYTHING you could need provided in the clean and comfortable room, with many extras such as bottles of water and snacks. The location of the hotel was better than we imagined as the owner told us about a lovely and scenic 1 mile walk along the boardwalk along the bay, which started right across the street from the Niantic Inn! . She gave suggestions for coffee shops and anything else we asked about. Personal and professional. A delightful stay! Thank you’ "
A verified traveller stayed at The Niantic Inn
Posted 1 day ago
The Niantic Inn