Holiday rentals in Woodbridge

4.73 out of 5 average rating, 494 reviews

Guest suite in Ansonia

Private Inn

Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

4.98 out of 5 average rating, 104 reviews

Flat in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

4.95 out of 5 average rating, 372 reviews

Flat in New Haven

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the heart of New Haven’s historic downtown, our designer home is part of the city’s most prestigious new luxury complex, renowned for its unmatched amenities and design. Highlights: • Prime location just steps from Yale University • Immaculately cleaned before every stay • Complimentary coffee, plush linens, and premium toiletries • 24/7 state-of-the-art fitness center • Expansive rooftop terrace with grills and chic lounges • Over 700 sqft of bright and sophisticated living space

4.93 out of 5 average rating, 141 reviews

Guest suite in Cheshire

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

5 out of 5 average rating, 11 reviews

Flat in Hamden

In-law Private Studio Apartment

Enjoy a stylish experience at this centrally-located studio apartment. Located in the quaint, quiet, and highly desirable Spring Glen neighborhood, it’s short walking distance of city bus line, as well as several local restaurants, cafes, & local entertainment. Centrally located to Yale University & Hospital, Quinnipiac University, SCSU, Albertus Magnus, as well as downtown Hamden & New Haven. The 400 sq ft apartment has a full bed w/ Tempur-Pedic mattress, & couch pulls out into a full bed.

4.94 out of 5 average rating, 18 reviews

Flat in New Haven

Spacious Garden Apt + Office with Private Entrance

A lovely ground-floor unit in the heart of New Haven. 2 minutes from a cute downtown area with cafes, shops, and world-class food. 5 minutes to Westville Bowl. 10 minutes to Yale University campus. This unit features art and decorative flair collected from around the world and offers privacy and restfulness in a spacious home. Queen bed and sofa sleeper bed. Also has a fully furnished kitchen, bathroom, washer/dryer, wifi, and a spacious backyard for your enjoyment.

4.93 out of 5 average rating, 55 reviews

Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

4.95 out of 5 average rating, 43 reviews

Home in Westville

7 Mins drive to Yale | Large fenced yard

Nestled in the charming neighborhood of New Haven, our home offers the perfect blend of tranquility and convenience. You'll enjoy a peaceful retreat surrounded by tree-lined streets, all while being just a stone's throw away from the vibrant energy of Yale University and the cultural richness of New Haven. Explore local parks, dine at renowned restaurants, and discover the city's unique character, all from your cozy home base in New Haven.

4.99 out of 5 average rating, 97 reviews

Flat in Westville

Retreat in New Haven by Stephanie and Damian

Welcome to your personal retreat in the heart of Westville. This apartment has a spacious spa-like bathroom, and cozy living room with an amazingly comfy couch and large flatscreen tv. You will relax in a cloud of comfort in this centrally located oasis, where you'll find yourself near Yale's football stadium, Westville Bowl music venue, local art studios, quaint coffee shops, and famous restaurants just steps from your door.

4.94 out of 5 average rating, 308 reviews

Guest house in Westville

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

4.93 out of 5 average rating, 233 reviews

Flat in Westville

Perfect for Yale and New Haven Visits

We purchased the house containing this apartment in 2017, and have been steadily updating and modernizing the space. Beautiful, recently refreshed apartment in a circa 1895 Victorian home. Hardwood floors throughout, and newly redone kitchen and bathroom. Ideally located in a historic neighborhood, with easy access to Yale University and athletic fields, Westville Music Bowl, Hopkins school, and Downtown New Haven.

4.97 out of 5 average rating, 29 reviews

Flat in East Rock

Cozy East Rock apartment

A spacious and serene space in the heart of East Rock inside a historic home. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The private bedroom has a king bed and a shower/bathroom. The sofa in the living room converts to a second bed (queen width) and a second full bathroom (with shower and tub) is located by the kitchen.

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Popular amenities for Woodbridge holiday rentals

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Other great holiday rentals in Woodbridge

4.93 out of 5 average rating, 85 reviews

Private room in Hamden

Cozy Bedroom in shared Queer home - women only

RebeccaRating, 5 stars6 days ago

Very friendly host! Made us feel comfortable and safe. Clean house and room. There are children in the house, so we heard them playing in the morning, but it was of no issue to us.

Private room in New Haven

4.89 out of 5 average rating, 27 reviews

Aesthetic Room 6 Min From Yale

GeraldineRating, 5 stars1 month ago

Daiana was incredibly helpful and accommodating with all my questions. The apartment is lovely, with a wonderfully powerful shower! The neighbourhood is very residential with no nearby shops or restaurants. But if you are going to an event at the Yale Bowl or nearby sports area (which I was), it is very convenient. And it is less than 10 minutes by car or Uber from downtown New Haven. Daiana's beautiful apartment and very friendly attitude made my stay memorable. Highly recommended!

Private room in East Rock

4.96 out of 5 average rating, 395 reviews

Comfy room for up to three guests

YJRating, 5 stars1 month ago

If I could give more than 5 stars, I would. This is the kind of place that makes Airbnb truly special. I hope it gets the recognition it deserves—but at the same time, it’s so perfect that a part of me wants to keep it a secret. Shelly redefines what it means to be a host—warm, thoughtful, and genuinely caring. From the moment I reached out, she was incredibly responsive and kind, even across different time zones. She made sure everything was ready for us with care and intention. My friends and I arrived to find a spotless, peaceful home that felt more like a retreat than a rental. There were small gestures throughout that made us feel welcomed and cared for—Shelly had anticipated what we might need before we even thought of it. Her warmth showed in every detail. All of us agreed: we’ll definitely stay here again next time we’re in New Haven. We’ll miss Shelly and the peaceful haven she’s created. It was truly a home away from home.❤️We'll miss you, Shelley!

Private room in New Haven

4.85 out of 5 average rating, 34 reviews

Chapel Room

TeresaRating, 5 stars1 month ago

This was the perfect place for a few day trip to visit New Haven. I was only ever a 10-20 minute walk from the house and it is on a quiet street. There are a couple other rooms occupied but I almost never ran into any one else! If i did people were friendly. The kitchen came in handy and the other amenities were appreciated (wifi, clean bathroom, other furnished and comfy common spaces). I think the most gratitude I felt was at checkout when I was delayed in leaving and I was quickly accommodated. Thanks to Naomi for the lovely stay!

Private room in Westville

4.83 out of 5 average rating, 18 reviews

Quiet rm. with private entrance, at edge of woods

DavidRating, 5 stars3 weeks ago

Everything was perfect for my stay, the room was clean private and very comfortable with its own private entrance. I loved the location in a quiet area next to a beautiful nature park. Sascha has set up the house providing everything that I wanted and it has a very happy wholesome feel to it.

Private room in New Haven

4.98 out of 5 average rating, 107 reviews

3 Welcome to the New Haven Experience

MarijkaRating, 5 stars3 months ago

I will definitely stay here again in the future and highly recommend this place! It was very clean and cozy, Katy was really responsive and friendly, and I appreciated the list of recommendations for things to do as I am not local to Connecticut.

4.98 out of 5 average rating, 93 reviews

Private room in Hamden

Budget meets Boho-Chic!

DanielRating, 5 stars6 days ago

Fantastic hosts, very welcoming and accommodating. Room was very comfortable and clean. I appreciated the well stocked shower. Guestbook had lots of good local dining and activity recommendations. Would definitely return next time I stay in the New Haven area.