Shelter Island Vacation Rentals

Aurora Rossi

Are you in a hurry?

Here is a quick list of Vacation Rentals in Shelter Island, selected based on their rating

Name of hotel Accommodation Rating Price, $
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

9.6 / 10

(115 Reviews)

From 140$
Fancy Studio Private Entrance

9.3 / 10

(72 Reviews)

From 105$
Riverside Retreat-Waterfront Walkout Apartment

9.5 / 10

(82 Reviews)

From 286$
Downtown New Haven, Spacious Stay By Yale - Ao Destinations

8.8 / 10

(192 Reviews)

From 117$
The Pines Men-Only Stay

9.8 / 10

(82 Reviews)

From 300$

Vacation rentals in Shelter Island offer an array of options for travelers seeking a peaceful retreat surrounded by nature. From charming cottages to luxurious waterfront homes, there is something to suit every preference and budget. This destination, known for its natural beauty and tranquil atmosphere, is ideal for families, couples, and groups looking to unwind. Explore various rental types that provide convenient access to local attractions and serene landscapes. With the right selection, your stay can be filled with comfort and memorable adventures.

Best Shelter Island Vacation Rentals

Table of contents

Shelter Island Retreat W/ Outdoor Pool! Sandpoint By Rove Travel - 6Br Family Home With Pool King-Bed Room With Private Bath -Free Wifi-- New London-Mystic Fancy Studio Private Entrance Riverside Retreat-Waterfront Walkout Apartment Downtown New Haven, Spacious Stay By Yale - Ao Destinations The Pines Men-Only Stay Villa Signor The Cliffside Resort Condominiums Private Apt King Suite, L.I, Ny-Hamptons To Nyc

View all photos

10
Excellent
1 Reviews

Shelter Island Retreat W/ Outdoor Pool!

📍 78 S Ram Island Dr
Check Availability

View all photos

10
Excellent
1 Reviews

Sandpoint By Rove Travel - 6Br Family Home With Pool

📍 Brander Parkway 13
Check Availability

View all photos

9.6
Excellent
115 Reviews

King-Bed Room With Private Bath -Free Wifi-- New London-Mystic

📍 239 Williams Street

From 140$

Check Availability

View all photos

9.3
Excellent
72 Reviews

Fancy Studio Private Entrance

📍 28 Ormond Avenue

From 105$

Check Availability

View all photos

9.5
Excellent
82 Reviews

Riverside Retreat-Waterfront Walkout Apartment

📍 622 Military Highway

From 286$

Check Availability

View all photos

8.8
Excellent
192 Reviews

Downtown New Haven, Spacious Stay By Yale - Ao Destinations

📍 32 Elm Street

From 117$

Check Availability

View all photos

9.8
Excellent
82 Reviews

The Pines Men-Only Stay

📍 488 Tarpon Walk

From 300$

Check Availability

View all photos

9.1
Excellent
103 Reviews

Villa Signor

📍 311 Old Pond Lane

From 236$

Check Availability

View all photos

9.2
Excellent
221 Reviews

The Cliffside Resort Condominiums

📍 61475 Route 48

From 513$

Check Availability

View all photos

9.3
Excellent
52 Reviews

Private Apt King Suite, L.I, Ny-Hamptons To Nyc

📍 1 Martin Street

From 123$

Check Availability

View all photos

8.7
Excellent
65 Reviews

Historic Peaceful Apartment

📍 105 Newhall Street 1

From 123$

Check Availability

View all photos

10
Excellent
17 Reviews

New! Updated Mystic Home W/ Sauna, Hot Tub & Deck

📍 156 Dartmouth Dr.

From 310$

Check Availability

View all photos

9.2
Excellent
45 Reviews

Cozy Garden Apartment Along The Shoreline

📍 14 Charles St

From 202$

Check Availability

View all photos

9
Excellent
88 Reviews

Hyatus Luxury Residences City Crossing

📍 9 Tower Lane

From 289$

Check Availability

View all photos

8.5
Very good
74 Reviews

Beautiful Studio Apartment In Historic House

📍 105 Newhall Street

From 175$

Check Availability

View all photos

9.4
Excellent
30 Reviews

Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed

📍 656 Orange Street

From 326$

Check Availability

View all photos

9.4
Excellent
14 Reviews

Historic Essex Home W/ Large Yard Near Downtown!

📍 73 West Avenue

From 261$

Check Availability

View all photos

10
Excellent
2 Reviews

Charming Old Saybrook Cottage < 1 Mi To Beach

📍 7 Fenwood Pkwy

From 221$

Check Availability

View all photos

9.4
Excellent
14 Reviews

New London Hideaway Near Beaches & Local Spots!

📍 91 Squire St

From 309$

Check Availability

Location