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House holiday rentals in Shelter Island Heights

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Top-rated house rentals in Shelter Island Heights

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

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Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

4–11 Apr

$693 SGD per night

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 195 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

6–13 Dec

$1,191 SGD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

2–9 Jun

$1,185 SGD per night

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

New, immaculate, all-season home by the beach with crisp designer details. Every detail was considered for maximum enjoyment. The heated saltwater pool (open April-Nov) hot tub, fenced in yard & deck gets sun all day. Located in the village of Sag Harbor, steps from the Bay and Main Street & all the Hamptons has to offer. Come feel the vacation vibes as soon as you arrive. The central location, luxurious finishes, breathtaking sunsets on the sandy beach make this the perfect year-round getaway.

17–24 Nov

$1,017 SGD per night

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (open 04/19 - additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool, shoot hoops, or take a 15 minute walk to the private (and empty) bay beach where you can use my paddle board. Or drive to the famous Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg 22-1590 Local taxes included

23–30 Oct

$935 SGD per night

Guest favourite

Home in East Lyme

4.96 out of 5 average rating, 105 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

21–28 Feb

$205 SGD per night

Guest favourite

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

11–18 Jun

$1,168 SGD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

29 Jan – 5 Feb

$165 SGD per night

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

8–15 Oct

$593 SGD per night

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 222 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

9–14 Jun

$615 SGD per night

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

17–24 Mar

$1,098 SGD per night

Guest favourite

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

2–9 Sep

$1,052 SGD per night

Holiday rentals for every style

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Popular amenities for house rentals in Shelter Island Heights

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

7–14 Nov

$1,235 SGD per night

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

6–13 Dec

$709 SGD per night

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

10–17 May

$822 SGD per night

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

2–9 Nov

$307 SGD per night

Guest favourite

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

1–8 Jan

$1,497 SGD per night

Guest favourite

Home in Cutchogue

4.87 out of 5 average rating, 116 reviews

The Perfect North Fork Escape

13–20 Oct

$779 SGD per night

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

29 Oct – 5 Nov

$1,124 SGD per night

Home in East Hampton

4.88 out of 5 average rating, 101 reviews

Gorgeous East Hampton Getaway

19–26 Nov

$1,088 SGD per night

Weekly house rentals

Guest favourite

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

10–17 May

$823 SGD per night

Guest favourite

Home in East Marion

4.83 out of 5 average rating, 6 reviews

Private North Fork Cottage- Walk to Beach!

5–12 Nov

$324 SGD per night

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

9–16 Dec

$585 SGD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

19–26 Nov

$744 SGD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

8–15 Nov

$821 SGD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

3–10 Nov

$885 SGD per night

Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 10 reviews

Spacious house with pool.

10–17 Jul

$1,260 SGD per night

Guest favourite

Home in Greenport

4.99 out of 5 average rating, 71 reviews

Beach House in L.I. Wine Country

24–31 Oct

$651 SGD per night

Private house rentals

Guest favourite

Home in Greenport

4.95 out of 5 average rating, 40 reviews

The North Star: Greenport Waterview Beach Getaway

16–23 Jan

$885 SGD per night

Guest favourite

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

24–31 Dec

$596 SGD per night

Home in Shelter Island

4.88 out of 5 average rating, 69 reviews

Charming 4BR Cottage on Shelter Island

3–10 Sep

$778 SGD per night

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Waterfront Greenport Boathouse

16–23 Dec

$812 SGD per night

Home in Greenport

4.9 out of 5 average rating, 20 reviews

modern 3 bedroom home with fireplace

20–27 Dec

$897 SGD per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 22 reviews

Primely located Sag Harbor Village home

11–18 Jun

$817 SGD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

24 Sep – 1 Oct

$786 SGD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 44 reviews

The Big Easy... A gentle, slow and easy going stay

14–21 Dec

$832 SGD per night

Quick stats about house rentals in Shelter Island Heights

Total rentals
190 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
5.5K reviews
Nightly prices starting at
$162 SGD before taxes and fees

Destinations to explore