Vacation rentals in Woodbridge

4.88 out of 5 average rating, 109 reviews

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.

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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.

4.99 out of 5 average rating, 119 reviews

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.

LocationFamilyLong stay

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.

4.95 out of 5 average rating, 125 reviews

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

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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.

4.94 out of 5 average rating, 161 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.

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4.97 out of 5 average rating, 143 reviews

A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.

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.

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A well-appointed bedroom features a spacious bed with neutral-toned bedding, flanked by two wooden nightstands with lamps. Decorative wall accents and a potted plant enhance the inviting atmosphere. Natural light filters through the window, illuminating the warm hardwood flooring and soft area rug.

4.96 out of 5 average rating, 75 reviews

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.

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4.92 out of 5 average rating, 354 reviews

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 New Haven

Westville Hideaway | Stylish Guesthouse + Parking

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

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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.

5.0 out of 5 average rating, 205 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!

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An elegant entryway frames a view of a dining area furnished with a large wooden table surrounded by chairs. A vintage-style bar cart, stocked with various beverages, is positioned to one side, contributing to a refined atmosphere. Warm wood accents complement the bright and inviting space.

4.89 out of 5 average rating, 245 reviews

Large Designer Westville house! Walk to Yale Bowl

Large pristine 2 bedroom, perfect location, set up specifically for the luxury traveler. Central a/c and heat. Cozy living room with extra large, sofa, well-stocked kitchen, huge dining table, comfortable and very quiet bedrooms with black out curtains, memory foam mattresses (Tuft & Needle), and super soft sheets bamboo cooling sheets. Centrally located house with all the amenities of home. Safe and quiet, cute walk-able area!

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Superhost

An outdoor space features a heated pool with a clear blue surface, surrounded by a spacious deck. Lounge chairs and shaded seating areas are arranged nearby, offering comfort and relaxation. Lush greenery borders the area, enhancing the tranquil atmosphere.

Home in Hamden

4.83 out of 5 average rating, 83 reviews

Modern home with a private Heated pool and jacuzzi

In our home-away-from-home, enjoy hotel luxury with more space to feel at home. Our mission is to provide you with more space, less contact, and modern design. Whether for business or leisure, our rooms are perfect for you. We offer keyless entry and exceptional cleaning standards. Conveniently located near Wintergreen Lake and just 12 minutes from Downtown New Haven, get ready to experience the best of New Haven!

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Guest suite in Woodbridge

A spacious two-story house is framed by lush green grass and landscaped gardens. A circular driveway leads to the entrance, flanked by trimmed hedges and a small tree at the center of a mulched bed. Large windows reflect the surrounding greenery.

4.91 out of 5 average rating, 173 reviews

Cupola Hill -a 2 BR guest suite with bucolic views

Beautiful 2 bedroom guest suite attached to main house with separate entrance, bathroom, living room. Set on magnificent 20 acre estate, perfect country get away, only 15 minutes to Yale and downtown New Haven. It’s the best of both worlds! Come enjoy the great restaurants of New Haven and then head to Cupola Hill for an evening in the country! Have a glass of wine under the stars and watch the wildlife!

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A large brick house with a distinctive gabled roof and charming architectural details is surrounded by lush greenery and blooming flowers. The welcoming exterior features well-maintained landscaping and pathways leading to the entrance. The sky is clear, contributing to a bright and airy appearance.

4.98 out of 5 average rating, 123 reviews

Large group haven! Sleeps up to 20!

Spacious, stylish, and perfect for groups! This bright 6BR home near Yale has room for everyone—2 cozy lounge areas, Smart TVs, foosball, a fully stocked kitchen, and flexible sleeping setups. Located in a quiet neighborhood just minutes from Downtown, SCSU, and Tweed. Great for family trips, celebrations, or weekend getaways. Self check-in, fast WiFi, free parking, and all the comforts of home!

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Popular amenities for Woodbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Woodbridge

A stylish living area features a dark green accent wall adorned with decorative wall hangings. A black velvet sofa offers seating, complemented by two green armchairs. Central round coffee tables sit on a patterned area rug. Natural light filters through sheer curtains, enhancing the inviting space.

4.96 out of 5 average rating, 74 reviews

Serene Bohemian Paradise *420 friendly*

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A charming exterior of a multi-story house is presented, featuring green siding and classic white columns. Potted plants hang from the balcony, while lush greenery frames the entry, creating a welcoming atmosphere. Sunlight highlights the architectural details and vibrant colors.

4.93 out of 5 average rating, 28 reviews

Esther’s Retreat Two

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4.84 out of 5 average rating, 86 reviews

Home in Hamden

Game room retreat with fire pit near Yale

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4.97 out of 5 average rating, 78 reviews

A tranquil view of Swan Lake is captured, surrounded by autumn foliage. Colorful outdoor chairs are positioned on a leaf-covered shore. Sunlight reflects off the calm water, creating a serene atmosphere that invites relaxation.

Home in Oxford

Lakefront Summer Oasis - kayak, fish and get cozy!

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4.88 out of 5 average rating, 81 reviews

The exterior of a two-family house is displayed, featuring a light blue siding and maroon shutters. A manicured lawn surrounds the property, with shrubs and a small, decorative tree visible. Stairs lead to a covered entrance, providing access to the self-contained apartment.

Apartment in West Haven

Fully furnished 2nd floor apt. 4 rooms 2 bedrooms

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4.99 out of 5 average rating, 79 reviews

An aerial view captures a charming beach cottage surrounded by greenery, with the expansive beach and ocean visible in the distance. The vibrant blue water contrasts with the sandy shore, while the quiet neighborhood adds to the serene atmosphere.

Home in West Haven

Relaxing Waterview Getaway

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Superhost

Home in Seymour

4.84 out of 5 average rating, 19 reviews

Cozy Woodland Haven on a Quiet Street

QuietBathroomWifi

A charming home is framed by vibrant red and orange foliage, indicative of the fall season. The exterior features a light grey facade with white trim and welcoming porch steps. A stone wall borders the lush garden, creating an inviting atmosphere for guests.