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.

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Top Guest favourite

A spacious deck features multiple blue Adirondack chairs, all facing the tranquil waters of Long Island Sound. The horizon showcases a gentle gradient of pastel colors, signaling the transition from day to evening, while the calm water reflects the serene atmosphere.

Holiday home in Guilford

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

Top Guest favourite

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Apartment in Milford

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, 651 reviews

Top Guest favourite

Apartment in New Haven

Elegant Modern Stay Near Yale • Gym • Roof Terrace

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! Broadway lies just around the corner and some of New Haven’s best Pizza a stone’s throw away you’d be hard-pressed to find a better location for your stay. Enjoy cooking up a nice dinner at home one night using the fully-equipped kitchen provided. Spend the evening on the rooftop terrace watching the sunset over the city skyline before tucking in for the night. Use the downstairs gym for a morning workout.

4.94 out of 5 average rating, 188 reviews

Guest favourite

A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.

Cottage in Milford

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

Top Guest favourite

A comfortable living area features a light-colored sofa, two leather chairs, and a wooden coffee table. A flat-screen TV is mounted on the wall, with decorative artwork above it. Soft curtains frame the windows, allowing natural light to fill the space.

Apartment in New Haven

Gemstone: Family-friendly, Close to Yale/Downtown

Welcome to Gemstone! Nestled on a quiet, tree-lined street, this architect designed space is just minutes from Yale Campus and downtown New Haven. Both beautiful and functional, it has been fully renovated and thoughtfully crafted to feature both modern and classic elements. In addition to two bedrooms and two full bathrooms, it includes everything you need to feel comfortable: central air, washer/dryer, WiFi, a 4-seat breakfast bar, new appliances, easy parking, and a 6-person dining table.

4.99 out of 5 average rating, 123 reviews

Top Guest favourite

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

4.97 out of 5 average rating, 270 reviews

Top Guest favourite

Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

4.99 out of 5 average rating, 113 reviews

Superhost

A bright living area features large windows, allowing natural light to fill the space. A comfortable gray sofa sits alongside a round coffee table and a cozy armchair. The open kitchen is equipped with modern appliances and sleek cabinetry, ideal for a relaxing stay.

Apartment in New Haven

Luxurious 3BR Apartment w/ Parking & Gym

Our prime location meets modern elegance. This three-bedroom spacious apartment is designed for comfort, convenience, and sophistication in the heart of a dynamic urban community. Whether planning a quiet night in or a lively evening downtown, Hyatus amenities elevate your living experience. º Rooftop Sky Lounge with an outdoor TV º Screening area º Cabanas º Billiards º Bocce courts º Fireside lounge º Co-working space featuring private work pods º Meeting rooms º Cappuccino Bar

4.95 out of 5 average rating, 129 reviews

Top Guest favourite

A bright and modern kitchen area features white cabinetry and stainless steel appliances. A large island is equipped with seating for three, while a cozy living space with two leather chairs is visible in the background. Natural light filters through multiple windows.

Apartment in New Haven

The Winchester House at Science Park-Yale

Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

5.0 out of 5 average rating, 209 reviews

Guest favourite

A cozy sleeping area features a wooden bed frame adorned with decorative pillows, flanked by two bedside tables. A light blue throw is draped over the bed. A comfortable seating area includes a round table and armchair, complemented by a soft rug covering the floor.

Apartment in New Haven

Modern Urban Getaway | Near Yale + Downtown

Beautiful and private Airbnb apartment located in New Haven. Peaceful, bright, immaculate and thoughtfully appointed is the best way to describe the Urban Sanctuary. You will fall in love with our cozy and charming garden apartment, nestled in a historic 3 family home in Westville. You will find good restaurants and coffee shops around, it's just the best place for you to stay. We provide a variety of amenities.

4.93 out of 5 average rating, 355 reviews

Top Guest favourite

Home in Fairfield

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.

4.96 out of 5 average rating, 233 reviews

Guest favourite

Apartment in New Haven

Soaking Tub Retreat | Cozy Luxe Stay Near Yale

Relax in this peaceful retreat just 10 minutes from downtown New Haven and Yale. Ideal for solo travelers or anyone seeking a quiet escape. Enjoy the deep soaking tub, calming decor, fast Wi-Fi, and a serene space to recharge. No parties—just peace, comfort, and good vibes. This is a calm, intentional space for peaceful stays only. We welcome guests who appreciate good energy and quiet rest.

4.97 out of 5 average rating, 119 reviews