Vacation rentals in Woodbridge

4.93 out of 5 average rating, 269 reviews

A scenic beach scene captures individuals enjoying a relaxing day by the water. Sun loungers are positioned in the soft sand, with gentle waves lapping at the shore and a vibrant blue sky filled with fluffy white clouds.

Cottage in Guilford

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

4.98 out of 5 average rating, 166 reviews

The entrance area features a welcoming glass door leading to a bright hallway. A set of wooden stairs ascends to the upper levels, with light illuminating the space through a nearby window. The floor is finished in a dark, textured material.

Vacation home in Warren

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

4.92 out of 5 average rating, 205 reviews

A private backyard space features a wooden gazebo with a seating area, surrounded by a gravel surface. Comfortable wicker furniture, including a sofa and chairs, invites relaxation. The fenced yard offers a sense of privacy, complemented by beach gear visible in the background.

Guesthouse in Milford

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

5 out of 5 average rating, 10 reviews

Home in Roxbury

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

4.79 out of 5 average rating, 43 reviews

Two comfortable chairs are positioned on a spacious porch, offering a clear view of the beach and ocean. The horizon is visible in the distance, with calm waters under a blue sky dotted with clouds.

Home in West Haven

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

4.94 out of 5 average rating, 114 reviews

A spacious outdoor dining area features a large wooden table surrounded by matching chairs. Sunlight illuminates the area, showcasing a well-maintained yard with a manicured hedge and a small garden shed visible in the background.

Home in Northport

Cool pad, Private Rms, Walk to village, Wtr view

Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

5 out of 5 average rating, 61 reviews

Home in Farmington

Lake Escape: Lake Cottage Charm, Lake Front, AC

Direct lakefront access with gorgeous views on a private lake. This beautiful 1930's lakefront cottage was fully renovated and reimagined by its owners in 2021. Custom architectural trim and details can be found throughout blending this homes' heritage with modern amenities. 2 bedrooms, eat-in kitchen and window seat nook, 2 full baths, custom barn doors and cabinetry, a reimagined sunroom, beautiful views on 100' of accessible lake frontage with outdoor patio, 1 mile from town center.

4.98 out of 5 average rating, 110 reviews

A sandy beach scene is visible, framed by wooden fencing leading to the shoreline. Colorful umbrellas dot the beach, with visitors lounging on towels, while gentle waves lap at the shore. A clear sky adds to the serene coastal atmosphere.

Cottage in Hampton Bays

Hamptons Waterfront- Relax & Getaway!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Conveniently located just minutes from the center of town for all your shopping needs; grocery store, Starbucks, 7-11, rite-aid, bagel cafe, pizzaria, farmers market and more.

5 out of 5 average rating, 102 reviews

A well-lit wooden deck features comfortable seating arrangements with padded chairs, perfect for relaxation. Soft lights illuminate the space, creating a welcoming atmosphere. A protective railing borders the deck, with a view of a privacy fence in the background.

Home in Milford

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

4.9 out of 5 average rating, 100 reviews

A charming building is illuminated by soft evening light, surrounded by blossoming trees adorned with twinkling lights. Outdoor seating is visible, inviting guests to enjoy the vibrant atmosphere of the town. The sky transitions to a serene twilight blue, enhancing the scene.

Guest suite in Branford

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

4.92 out of 5 average rating, 117 reviews

Home in New Fairfield

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

5 out of 5 average rating, 11 reviews

A small outdoor seating area features a round table with a woven tray holding glasses, complemented by two comfortable chairs. The view extends over the calm waters of the Peconic River, with boats moored nearby and trees lining the shore under a clear blue sky.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

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Popular amenities for Woodbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Woodbridge's top sights

Edge of the Woods Market6 locals recommend

Bella's Cafe11 locals recommend

West Rock Ridge State Park11 locals recommend

Southern Connecticut State University9 locals recommend

Yale Bowl4 locals recommend

Super Stop & Shop3 locals recommend

Other great vacation rentals in Woodbridge

Apartment in Downtown Stamford

A stylish lobby area features large glass walls allowing natural light to flood the space. Lush greenery is displayed in various decorative pots, enhancing the vibrant atmosphere. Comfortable seating is arranged on a patterned rug, providing a welcoming environment for guests.

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

4.93 out of 5 average rating, 319 reviews

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

4.94 out of 5 average rating, 31 reviews

The living room features a modern design with a curved green and orange sofa surrounding a light wood coffee table. A striking black fireplace provides a focal point against a light wall. A statue and decorative elements contribute to the welcoming ambience.

Home in West Haven

Westshore Luxury

5 out of 5 average rating, 13 reviews

Cottage in North Fork

Lovely North Fork Beach Cottage (2 BR/2 bath)!

4.94 out of 5 average rating, 68 reviews

The spacious kitchenette features modern appliances, including a refrigerator and a stove, set against rustic wooden beams and a brick fireplace. Natural light filters through the wooden windows, illuminating the inviting wood flooring and enhancing the open layout.

Cottage in Norwalk

Seaside Serenity: 2B 1B, Patio,Near Beach

4.95 out of 5 average rating, 20 reviews

A large beach house is visible, featuring multiple gables and a spacious deck with balcony. The facade is painted in light grey, complemented by white trim. In the foreground, sandy beach leads toward the house, framed by green grass and shrubs on either side.

Home in West Haven

Beach House steps from sand & Amazing Views

4.89 out of 5 average rating, 488 reviews

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

Great little place just for a couple