Dering Harbor Holiday Rentals, Shelter Island: Private House Rentals

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Go beyond your typical stay in Dering Harbor

Pet friendly

Apartment

Pool

Condo

Spa

Hot tub

Family friendly

Cottage

Waterpark

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Our top choices for Dering Harbor hotels

Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio

1. The Harbor Front Inn

Greenport

Michael

฿8,555

฿10,714 total

includes taxes & fees

4 Oct - 5 Oct

Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking

2. Zey Hotel

Greenport

Renee

฿5,551

฿6,341 total

includes taxes & fees

15 Sept - 16 Sept

3. The Pridwin Hotel

Shelter Island Heights

Anna

฿17,657

฿22,190 total

includes taxes & fees

15 Sept - 16 Sept

4. The Menhaden

Greenport

Lisa

฿12,996

฿16,164 total

includes taxes & fees

17 Sept - 18 Sept

5. Silver Sands Motel & Beach Bungalows

Greenport

Sirikhwan

฿11,052

฿12,627 total

includes taxes & fees

21 Sept - 22 Sept

6. Sound View Greenport

Greenport

Irene

฿9,621

฿13,810 total

includes taxes & fees

28 Sept - 29 Sept

7. Cliffside Resort Condominiums

Greenport

Christine

฿9,600

฿13,900 total

includes taxes & fees

30 Sept - 1 Oct

Cottage, 2 Bedrooms, Patio | Living room

8. North Fork Resort

Greenport

Lisa

฿11,742

฿13,416 total

includes taxes & fees

5 Oct - 6 Oct

9. American Beech Hotel

Greenport

Mary

฿8,848

฿11,425 total

includes taxes & fees

9 Sept - 10 Sept

10. Oyster Estate

Greenport

Jenny

฿11,315

฿14,256 total

includes taxes & fees

5 Oct - 6 Oct

A house with a porch, a sign reading "House on Chase Creek," and a tree with red leaves.

11. House on Chase Creek

The Heights

Calvin

฿7,081

฿8,090 total

includes taxes & fees

5 Oct - 6 Oct

12. The Chequit

The Heights

Kristin

฿6,809

฿7,779 total

includes taxes & fees

4 Oct - 5 Oct

13. Shelter Island House

Shelter Island Heights

Dorothy

฿6,625

฿7,569 total

includes taxes & fees

4 Oct - 5 Oct

The Shoals Grand Suite | Private kitchen

14. The Shoals Suites and Slips

Southold

Melissa

฿6,638

฿8,407 total

includes taxes & fees

1 Oct - 2 Oct

Suite, 1 King Bed, Kitchenette (Living Room) | Living room

15. West Neck Guesthouse

Shelter Island Heights

Allie

฿10,320

฿11,791 total

includes taxes & fees

9 Sept - 10 Sept

16. Sag Harbor Inn

Sag Harbor

Loretta

฿10,657

฿12,176 total

includes taxes & fees

4 Oct - 5 Oct

17. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Theresa

฿3,327

฿3,826 total

includes taxes & fees

4 Oct - 5 Oct

18. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Carolyn

฿2,806

฿3,227 total

includes taxes & fees

10 Sept - 11 Sept

19. Saybrook Point Resort & Marina

Old Saybrook Center

Florence

฿11,479

฿14,352 total

includes taxes & fees

4 Oct - 5 Oct

20. The Captain Stannard

Westbrook Center

Deborah

฿7,694

฿8,540 total

includes taxes & fees

13 Sept - 14 Sept

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Top Dering Harbor Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"This was one night, strictly for sleeping. It worked perfectly for that. Everything was clean, supplies were adequate, shower was hot and plentiful, the HVAC worked fine, the bed was comfortable, and it was quiet all night. Friendly, easy check-in, and check out. Good location for me with several choices for good restaurants for dinner and breakfast. I would be happy to return."

Shorewood Inn

10/10 Excellent

"While initially I was struck that it is not an Inn by looks like a motel. HOWEVER, the he owners are so lovely and sweet. It is in walking distance of a nic restaurant as well as coffee etc. The grounds ar nicely maintained with pretty flowers and plants. And there are chickens!!! Mad sitting area in th back with furniture and lots of grass."

Hampton's Vacation Inn

10/10 Excellent

"Wonderful stay!! Loved this property and the staff. Clean, well kept. Beds were slightly uncomfortable but that wasn’t a big deal. Great location!"

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Water's Edge Resort & Spa

8/10 Good

"Excellent staff and location. The food was mediocre"

Sound View Greenport

10/10 Excellent

"A Beautiful and Peaceful Stay at Sound View Greenport I had a wonderful stay at Sound View Greenport and would highly recommend it to anyone looking for a relaxing getaway on the North Fork of Long Island. It’s a great place for couples, families, or anyone who simply wants to escape the busy city and enjoy some quiet time by the water. Greenport is also nearby, making it convenient to explore the local restaurants, shops, vineyards, and other attractions. If you’re planning a trip to Greenport or the North Fork, Sound View is definitely a place worth considering. I would happily stay here again! 🌅🌊❤️"

The Hampton Maid

10/10 Excellent

"Absolutely beautiful hotel, in peaceful setting with lovely amenities."

Sag Harbor Inn

10/10 Excellent

"Sag Harbor Inn was located in a beautiful spot and close to shops and restaurants. This was an excellent choice."

North Fork Resort

8/10 Good

"My sisters and I booked a 2 bedroom cottage for a long weekend around Greenport. The listing said it was a 2 bedroom with queen beds but when I arrived I realized one room was only a full so one of us had to sleep on the pull out couch for us all to be comfortable. You also definitely need a car. It’s a 45 min walk from the train station so if you’re coming from the city it’s not a convenient location and it’s off a busy road. The cottage did have lots of kitchen amenities and a grill which is great if you’re looking for some easy meals. The shower’s water pressure was great and the air conditioning was effective. Unfortunately you can’t open any windows because there are no screens in the windows and the area is buggy. Overall, the place was nice but the rooms are smaller than I expected and you’re far from everything (even the main reception and pool)"