
Holiday houses in New Haven County
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Top-rated holiday rentals in New Haven County
Guests agree: these stays are highly rated for location, cleanliness and more.

Home in Milford
4.92 out of 5 average rating, 26 reviewsLight-filled Beach House Steps from the Sand
Located in prime Bayview Beach, a one min stroll to the sandiest beach in Milford. Two floors with private patio. Main level: half-bath, Cooks kitchen with a 6 person dining area, living room with flatscreen. Upstairs: master w/king size bed & en-suite bath, kids bedroom w/ bunkbed, another full bath w/ tub. 3rd bedroom with queen bed and trundle twin. If you want a get-a-way from the city, or just an escape then come to this tucked-away home. Enjoy all that this coastline gem has to offer.

Home in Fairfield
5 out of 5 average rating, 8 reviewsNewly built twin beach house within steps to beach
Keep it simple at this peaceful and centrally-located home. Newly built in 2019! Premier beach living at its finest. Steps to Fairfield’s beaches and less than a mile to downtown restaurants, shops, and bars. Fenced backyard. Central air throughout. Decks off the front and back with a Weber grill. Furnished with luxury furniture, sheets, comforters, and pillows. Smart TVs in every bedroom and living room. Tesla charging station at the house. Identical home next door available for larger bookings

Cottage in Guilford
4.93 out of 5 average rating, 265 reviewsCharm + location. Walk to beach, town, & harbor.
We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Guesthouse in Milford
4.92 out of 5 average rating, 204 reviewsChic Coastal Retreat: Modern Apt Steps from Beach
Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Home in Roxbury
5 out of 5 average rating, 10 reviewsZoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT
PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

Home in West Haven
4.79 out of 5 average rating, 43 reviewsBeachside Retreat
***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Home in Milford
4.76 out of 5 average rating, 55 reviewsSky-Top on Private Sandy Beach
Charming two bedroom located on Silver Sands Beach with magnificent ocean views and full private beach access! Located in a cute, beachy, family-friendly neighborhood with tons of activities to do! 1-mile boardwalk at the end of our street and a national state park. You can also find some of the best restaurants and shops in downtown Milford (1-Mile away) and New Haven just 15 minutes away… New Haven pizza is a must while in CT!!! Unwind to breathtaking sunrises and sunsets all year round!

Home in Milford
4.95 out of 5 average rating, 22 reviewsLa Sirena Beach Cottage
Charming Milford Bayview Beach cottage. The perfect blend of coastal charm and comfort. Boasting 3 cozy bedrooms and an inviting outdoor space. You'll have a comfortable place to relax and unwind inside or out. Yet the real gem is our location -- just a short 2-minute walk to the beach, where you can soak up the sun, ride the waves or take a leisurely stroll along the shore. Whether you're seeking a romantic escape or a family vacation this cottage is tailored to meet your needs!

Home in Milford
5 out of 5 average rating, 5 reviewsSeaside Paradise
Welcome to our beach house in Milford! This getaway is just a short walk from the beach, making it the perfect vacation spot for families or groups of friends. Whether you're looking to soak up the sun on the sandy shores, explore the charming town of Milford, or simply relax in a comfortable beach house, our rental is the perfect choice. We can't wait to host you and make your beach vacation unforgettable. Book now and start counting down the days until your beachside getaway!

Guest suite in Branford
4.9 out of 5 average rating, 100 reviewsGranite Bay Getaway - Private Studio Apartment
Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Home in Milford
5 out of 5 average rating, 96 reviewsWaterfront!-Hot Tub-The Charles Island Beach House
Hot Tub on Deck overlooking LI Sound Build in 2016 92/92 5 Star Ratings Sound-on-Sound (Soundside Music Festival) – 9 Miles away Silver Sands Beach in Milford, CT. Open concept (2500 sq. feet), modern house directly on the water. Spectacular views of Long Island Sound and Charles Island. Sunsets on roof deck. Hot Tub, Outdoor Shower, Kayak/Paddle Boards, and lots more. NOTE: From May-Sep we only accept weekly rentals - Sat-Sat rentals.

Home in Milford
5 out of 5 average rating, 100 reviewsSteps2Beach, Fish Pond w/Tropical Backyard Oasis!
🌟 Special Discounts on Early Birds, Last-Minute Stays & 7+ Nights! 🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC, it’s the perfect retreat for beach days, nature adventures, & coastal charm!
Holiday rentals for every style
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Popular amenities for New Haven County holiday rentals
Other great holiday rentals in New Haven County

Guesthouse in Southbury
4.93 out of 5 average rating, 318 reviewsCharming Guest Cottage with Modern Amenities

Guest suite in Wolcott
4.92 out of 5 average rating, 50 reviewsModern cozy, pet friendly

Home in West Haven
4.94 out of 5 average rating, 18 reviewsBeach House steps from sand & Amazing Views

Home in Middletown
4.95 out of 5 average rating, 40 reviewsHot Tub and pool Home away from home

Home in Fairfield
4.71 out of 5 average rating, 7 reviewsModern Beach Area Vacation Home With Pool

Home in Milford
4.98 out of 5 average rating, 43 reviewsBeachfront paradise- come, stay, relax!

Guesthouse in Trumbull
4.95 out of 5 average rating, 20 reviewsCozy in laws suite in the woods

Home in Milford
4.92 out of 5 average rating, 244 reviewsBright and Breezy Cottage by the Sea
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