Greenport Vacation Homes

An aerial view of a harbor with boats, a ship, and a dock extending into the water.

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Our top choices for Greenport holiday homes

Beach Block Hideaway

Pipes Cove

Jessica0610@gmail.com A.

HK$4,300 total

includes taxes & fees

2 Aug - 3 Aug

American Beech in Greenport - Petite King Room 7

Greenport

Parent From The Heart, Inc. E.

HK$4,550 total

includes taxes & fees

19 Jul - 20 Jul

Aqua Vista

Pipes Cove

Sophia

HK$4,048 total

includes taxes & fees

9 Aug - 10 Aug

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

HK$5,638 total

includes taxes & fees

23 Jul - 24 Jul

American Beech in Greenport - Deluxe King 6

Greenport

Jeffrey

HK$5,159 total

includes taxes & fees

29 Jul - 30 Jul

Rogers Lake House (87) · CT College+Beach+USCGA

Old Lyme

Cheryl H.

HK$4,146 total

includes taxes & fees

20 Jul - 21 Jul

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Waterford

Michelle M.

HK$3,600 total

includes taxes & fees

28 Jul - 29 Jul

Adorable Cottage, 5 min walk to water & town

Westbrook Center

Donovan V.

HK$3,489 total

includes taxes & fees

20 Jul - 21 Jul

The Beach Nest-Lux Cottage Steps to the Beach

Clinton

Karol W.

HK$4,587 total

includes taxes & fees

19 Jul - 20 Jul

The Bay Cottage · Rocky Neck Park, Beach & Niantic

East Lyme

Sarah G.

HK$3,798 total

includes taxes & fees

20 Jul - 21 Jul

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Waterford

Elaine A.

HK$4,794 total

includes taxes & fees

13 Aug - 14 Aug

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

"My family and I had an ideal stay at Kristine's beachside cottage. Highlights include a short walk to the beach, a well stocked kitchen, easy and efficient temperature controls and my kids especially loved the bunk beds! It was perfectly cozy and comfy for a family of four. We stayed here in April, but I can only imagine how lovely the screened in porch and back deck would feel during warmer months. 5 stars!"

Leila N.

Coastal New England Waterfront Home, Harkness Park, Casinos

Waterford

Kathleen C.

HK$6,438 total

includes taxes & fees

19 Jul - 20 Jul

Villa Luz Family Home w/ heated pool & jacuzzi

Hampon Bays

Annie B.

HK$14,786 total

includes taxes & fees

21 Jul - 22 Jul

adorable ranch in beach community

Old Saybrook

Matthew V.

HK$6,589 total

includes taxes & fees

18 Jul - 19 Jul

BlackBerry Private home with jacuzzi yearlong

East Hampton

Suzanne R.

HK$13,478 total

includes taxes & fees

21 Jul - 22 Jul

Coffee/tea maker, fridge, microwave, oven

Work and Play Special! Extended Stay Discount

Shelter Island

Nava S.

HK$12,279 total

includes taxes & fees

22 Jul - 23 Jul

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

Saybrook Manor

Hayley T.

HK$5,933 total

includes taxes & fees

19 Jul - 20 Jul

Hampton Bays Townhouse - Pool, Beach Access

Hampton Bays

Eileen O.

HK$5,222 total

includes taxes & fees

14 Aug - 15 Aug

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Top Greenport Hotel Reviews

Bayview Resort

10/10 Excellent

"Very peaceful, clean, and very nice location. The staff were very polite and accommodating. It was like staying over a family members home. Will definitely go back."

The Bentley Hotel Southampton

10/10 Excellent

"The staff at check in and check out were helpful and friendly. The suite was beautiful and felt like home. Also the entire room was extremely clean. The bed sheets were so soft! Most hotels they are like sand paper. Wish I traveled to this area more so I could stay there again. Wonderful experience."

Silver Sands Motel & Beach Bungalows

10/10 Excellent

"We had a great stay at Silver Sands! From my first phone call to them and their suggestions on places to ride our bikes, to the good mornings and smiling faces, the mood was set for a good time. The rooms, although not our usual taste in decor, were adorably decorated and kept the "feel" of the original motel and it's retro vibe. The attention to detail was high with crisp yellow and blue robes and a mermaid handle on the shower door, to special pour coffee in the room and an adorable SMEG refrigerator! But by far it was the location and view that made it spectacular, not to mention the bon fire at night!! It was just the icing on the cake, so to speak. We sat and had some wine and crackers and just really relaxed and enjoyed ourselves. We will definitely look to go back there again. Our only suggestion would be to add a pool :)"

The Harbor Front Inn

8/10 Good

"We are return guests and stayed for two nights. There was a new parking charge of $29/day. One of the reasons for choosing this hotel is that they are pet friendly. Unfortunately, that meant our room had several carpet stains and smelled distinctly of nature’s miracle cleaner (which is better than pee). I can deal with the stains, although had me wondering if the bed was clean, but the smell was overpowering. In our past stays, at this property the room was clean and odor free, so maybe just one room. This and the $75 pet fee seemed like we were simply covering for the damage caused by the untrained pets of others. We took our dog on six walks per day and never left her unattended so as to keep up our end of it. Otherwise it is a nice property in a good location with great staff."

Budget Host East End

10/10 Excellent

"The rooms were clean and though the buildings were dated, it seems like it's been recently renovated and they are taking steps to upkeeping the rooms and maintenance though there is still some work to be done with the ceiling of the room and the carpeting coming undone in the rooms. I was traveling with my mother and our first room had a non cooling AC and had to be switched out thanks to Jose. Very kind staff. It switched our night around for sure. So glad they accommodated us when we needed it. It was a hot humid night, that would of not been fun. Thank you. Great convenient location too. Ended up enjoying our stay."

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