Holiday rentals in Plum Island

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Top-rated holiday rentals in Plum Island

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

26 Mar – 2 Apr

$1,005 SGD per night
Guest favourite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

28 Sep – 5 Oct

$459 SGD per night
Guest favourite

Guest suite in Groton

4.98 out of 5 average rating, 184 reviews

Babs Place - Groton, Ct

Clean spacious suite in a residential neighborhood sleeps eight. Centrally located. A child-friendly location with easy access from I-95. Private entrance, kitchen, off street parking, patio with grill, washer/dryer set up, and a dishwasher. Short drive to local historical and tourist locations such as CT wine trails, Clyde’s apple cider, downtown Mystic – the Aquarium, Seaport, and Village. Nautilus Museum, Ivryton and Godspeed Opera houses and Garde Arts Center. Decorated for the holiday.

9–16 Apr

$129 SGD per night

Popular amenities for Plum Island holiday rentals

Other great holiday rentals in Plum Island

Guest favourite

Home in Preston

4.96 out of 5 average rating, 595 reviews

Entire House Magical Waterfront Getaway

29 Dec – 5 Jan

$248 SGD per night
Guest favourite

Home in East Lyme

4.96 out of 5 average rating, 161 reviews

Beachfront Paradise

19–26 Nov

$581 SGD per night
Guest favourite

Cottage in Groton

4.95 out of 5 average rating, 269 reviews

Restored Historic Schoolhouse, Mystic River Views

31 Jan – 7 Feb

$169 SGD per night
Guest favourite

Barn in Essex

4.98 out of 5 average rating, 121 reviews

River Barn, Sidewalk Stroll into Essex Village

3–10 Apr

$615 SGD per night
Guest favourite

Guest suite in Groton

4.96 out of 5 average rating, 190 reviews

Private Guest Suite for Two

10–17 Apr

$170 SGD per night
Guest favourite

Holiday home in New London

5.0 out of 5 average rating, 108 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

2–9 Dec

$266 SGD per night
Guest favourite

Home in East Hampton

4.96 out of 5 average rating, 187 reviews

Ritz-East Hampton Cottage- 5 stars

13–20 Sep

$817 SGD per night
Superhost

Bungalow in Old Lyme

4.85 out of 5 average rating, 85 reviews

Insta-worthy * Couples Retreat

16–23 Dec

$240 SGD per night
Guest favourite

Flat in East Lyme

4.98 out of 5 average rating, 63 reviews

Lakefront Luxury on Pattagansett

25 Apr – 2 May

$206 SGD per night
Guest favourite

Home in Old Saybrook

4.98 out of 5 average rating, 47 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

14–21 Feb

$203 SGD per night
Guest favourite

Flat in Clinton

4.98 out of 5 average rating, 48 reviews

Cozy Shoreline Getaway

25 May – 1 Jun

$163 SGD per night
Guest favourite

Home in Orient

4.9 out of 5 average rating, 60 reviews

The Lane House | North Fork Private Beach Escape

7–12 Apr

$701 SGD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Southold
  6. Plum Island