
Holiday houses in Long Island Sound
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Top-rated holiday rentals in Long Island Sound
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Spacious Oceanfront Getaway with Spectacular Views
Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)
4.99 out of 5 average rating, 149 reviews
Beachfront Paradise
Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.
4.97 out of 5 average rating, 227 reviews
1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!
4.91 out of 5 average rating, 146 reviews
Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!
4.97 out of 5 average rating, 650 reviews
Cheerful 3 Bedroom Cottage with Fire Place
We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.
4.88 out of 5 average rating, 109 reviews
Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.
4.93 out of 5 average rating, 138 reviews
Savor Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated and featured as a top Airbnb by New York Magazine, 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. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.
4.98 out of 5 average rating, 184 reviews
Serene Waterfront Retreat - 400 ft Private Beach!
Welcome to a slice of waterfront heaven! Located on Milford's Cedar Beach, this newly renovated 3 bedroom / 1.5 bath home features over 400 feet of private beach. Enjoy breakfast prepared in the Chef's kitchen while watching one of the most radiant sunrises you will ever see. Stunning views from every room in the house. Wade into Long Island Sound with your own private beach. Located 3 doors down from the CT Audubon Society, known for its views & wildlife. We can't wait to host you!
4.99 out of 5 average rating, 159 reviews
Oceanfront Beach House w/ Private Hot Tub
Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.
4.94 out of 5 average rating, 145 reviews
The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.
4.96 out of 5 average rating, 462 reviews
Beautifully Restored Barn With New England Charm
Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.
4.96 out of 5 average rating, 355 reviews
The Katalpa House -by the beach
-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.
4.88 out of 5 average rating, 293 reviewsPopular amenities for Long Island Sound holiday rentals
Other great holiday rentals in Long Island Sound

Apartment in New Haven
4.94 out of 5 average rating, 142 reviews
Hang by the (Chel)SEA
5.0 out of 5 average rating, 45 reviews
White Cottage East Setauket
4.9 out of 5 average rating, 51 reviews
Stareway to Heaven
5.0 out of 5 average rating, 62 reviews
The Connecticut Cottage | Historic Modern Charm
4.97 out of 5 average rating, 31 reviews
Nama-stay: sweet Saugatuck Shores beach cottage
5.0 out of 5 average rating, 25 reviews
Bungalow by the Bay
5.0 out of 5 average rating, 3 reviews
RP modern cozy cabin
4.95 out of 5 average rating, 61 reviewsDestinations to explore
- Rentals with lake access Long Island Sound
- Barn rentals Long Island Sound
- Waterfront rentals Long Island Sound
- Family-friendly rentals Long Island Sound
- Cabin rentals Long Island Sound
- Bungalow rentals Long Island Sound
- House rentals Long Island Sound
- Loft rentals Long Island Sound
- Rentals with a sauna Long Island Sound
- Serviced apartment rentals Long Island Sound
- Luxury rentals Long Island Sound
- Guesthouse rentals Long Island Sound
- Rentals with a hot tub Long Island Sound
- Villa rentals Long Island Sound
- Boutique hotels Long Island Sound
- Cottage rentals Long Island Sound
- Apartment rentals Long Island Sound
- Holiday home rentals Long Island Sound
- RV rentals Long Island Sound
- Pet-friendly rentals Long Island Sound
- Rentals with breakfast Long Island Sound
- Rentals with beach access Long Island Sound
- Beachfront rentals Long Island Sound
- Bed and breakfasts Long Island Sound
- Private suite rentals Long Island Sound
- Townhouse rentals Long Island Sound
- Rentals with an accessible height toilet Long Island Sound
- Rentals with pools Long Island Sound
- Condo rentals Long Island Sound
- Rentals with an accessible height bed Long Island Sound
- Rentals with a kayak Long Island Sound
- Tiny house rentals Long Island Sound
- Hotel rooms Long Island Sound
- Farmstay rentals Long Island Sound
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