Holiday rentals in Woodbridge

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

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!

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

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

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!

Urban Garden Suite

Relax & Recharge in Westville’s Hidden Gem in. We Haven✨ Unwind in this serene, sun-filled, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. 💫 Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

Large Private Studio + Entrance + Bath

Large beautiful secluded studio with a private entry and private bath. Includes comfy queen size bed, futon sofa bed, free wifi, large smart TV with tons of movies, eat-in table for 4, microwave, mini-fridge, Keurig, toaster, closet w/ iron, and your own dedicated room temperature controls. Located in a beautiful, safe, and quiet neighborhood, the studio is attached to a split level house and located in the back on the lower level. It overlooks beautiful woodlands.

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.

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.