Vacation rentals in Woodbridge

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Top-rated vacation rentals in Woodbridge

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
An open bedroom suite is featured, with a warm-colored comforter covering a spacious bed. A wooden dresser stands beside the bed, and a leather couch is positioned against the wall. Natural light enters through windows, brightening the neutral-toned walls.
Guest suite in Ansonia
4.74 out of 5 average rating, 521 reviews

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

Top guest favorite
A white Dutch door is framed by rustic wooden walls, showcasing a combination of horizontal and vertical planks. A small lantern hangs nearby, and a woven basket adorns the wall beside the door. A simple bench with a patterned cushion sits on the side.
Guesthouse in Southbury
4.93 out of 5 average rating, 359 reviews

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).

Guest favorite
A cozy living space features a light-colored sofa with yellow accents, positioned beside a small round table. A striped area rug adds texture to the hardwood floor. Bright natural light enters through nearby windows, illuminating the space and connecting to the kitchen and bathroom beyond.
Apartment in Dwight
4.98 out of 5 average rating, 251 reviews

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.

Top guest favorite
Apartment in Milford
4.98 out of 5 average rating, 131 reviews

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.

Guest favorite
A spacious living area is illuminated by natural light streaming through large windows. A comfortable gray sofa with decorative pillows faces a modern coffee table. A stylish area rug adds color, while a wall-mounted TV and decorative plants enhance the space.
Apartment in New Haven
4.95 out of 5 average rating, 401 reviews

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

Top guest favorite
A serene waterfront view is presented, showcasing calm waters reflecting a soft pink sky. Lush green grasses frame the foreground, while a tree line marks the horizon, creating a tranquil landscape. A few ducks can be seen gently floating on the water.
Loft in Milford
4.94 out of 5 average rating, 166 reviews

Lovely water front lower-level loft, free parking

This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

Top guest favorite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 186 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top guest favorite
A cozy living room features a spacious blue couch adorned with yellow accent pillows. A wooden coffee table is positioned in front, with colorful artwork hanging on the walls. A large flatscreen TV is mounted for entertainment, enhancing the comfort of the space.
Apartment in Westville
4.98 out of 5 average rating, 119 reviews

Retreat in New Haven by Stephanie and Damian

Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

Superhost
A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.
Apartment in Brookfield
4.92 out of 5 average rating, 292 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Top guest favorite
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 Prospect Hill
5 out of 5 average rating, 163 reviews

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!

Guest favorite
A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.
Guesthouse in Westville
4.92 out of 5 average rating, 330 reviews

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.

Guest favorite
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 Edgewood
4.94 out of 5 average rating, 323 reviews

Urban Getaway

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.

Popular amenities for Woodbridge vacation rentals

When is the best time to visit Woodbridge?

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Frequently Asked Questions

  • How much does it cost to stay in apartment rentals in Woodbridge?

    Experience the best of Woodbridge with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Woodbridge have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Woodbridge. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Woodbridge?

    Woodbridge has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Woodbridge have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Woodbridge. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Woodbridge?

    Four-legged friends are welcome in Woodbridge. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Woodbridge have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Woodbridge. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Woodbridge have free parking?

    Absolutely! We offer over 10 apartment rentals with free parking in Woodbridge. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Woodbridge?

    Yes! Work meets play with ease at over 30 vacation rentals in Woodbridge featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Woodbridge?

    Make yourself at home in Woodbridge by choosing from our most frequently booked neighborhoods. We have over 1,030 vacation rentals in West New Haven, over 1,000 vacation rentals in West Rock, and over 950 vacation rentals in Westville.

  • What are the most popular amenities for Apartment Rentals in Woodbridge?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Woodbridge

  • Total vacation rentals

    Explore 60 vacation rentals in Woodbridge

  • Nightly prices starting at

    Woodbridge vacation rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 2,730 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Woodbridge vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodbridge rentals

  • 4.8 Average rating

    Woodbridge stays are highly rated by guests—averaging 4.8 out of 5!