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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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A serene beach view features soft sandy shores leading to calm waters. A small wooden bench is positioned in the foreground, while a sailboat glides gracefully on the horizon. Gentle waves can be seen lapping at the shoreline under a clear blue sky.

Home in Woodmont

4.92 out of 5 average rating, 26 reviews

Light-filled Beach House Steps from the Sand

FayeRating, 5 stars20 months ago

Mougeh's place is a lovely home with ample space, toys, books, games for entire family, within walking distance to the beach, and four mile drive to all shopping needs. The reason for the three star rating given in the "clean house" question was because when we arrived we noticed dog hair in the living area. We contacted the host and immediately the next day the cleaning service arrived and cleaned it. We were refunded the cleaning fee. Mougeh is very caring and responsive to her guests's needs.

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

4.93 out of 5 average rating, 267 reviews

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

AllisonRating, 5 stars2 months ago

This was my fifth stay in Jeanne's wonderful cottage! The cottage gets better and better each time I visit: a newly renovated bathroom, redecoration in lighter/brighter colors, etc. The home is extremely well stocked - every kitchen item you might need (including loads of glasses/plates/silverware, pots/pans, etc.), thick towels, extra blankets and throws, and lots of cleaning and paper products. There are plenty of cozy places to sit and relax, both indoors and out. The best thing of all is Jeanne herself, who is without a doubt the most generous host I've encountered on AirBnB. She is friendly, communicates proactively, and is quick to respond to any issues/questions. She truly opens her home to her guests, encouraging visitors to use the space fully and to make themselves at home. The cottage is an easy walk to the beach ane/or to town and is lovely, homey, and peaceful. I'll definitely return!

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

GeriRating, 5 stars4 weeks ago

It was our first experience with Airbnb. We were there to tour the World Headquarters for Jehovah’s Witnesses and this proved to be our evening haven. The house was well stocked as others had commented. We enjoyed relaxing and spent much time in living room with the beautiful view. It was perfect for our stay. Our thanks to our Host.

Top guest favorite

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

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

PatrickRating, 5 stars2 months ago

Rented this for six weeks while working in the area, was perfect. I enjoyed it very much. Lots of space everything you could possibly need even down to the toothpaste and brushes, you could seriously just show up completely unprepared and you would have an excellent stay. If I am back in the area for long term again this will be my first search.

A stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.

Farm stay in Kent

4.87 out of 5 average rating, 310 reviews

(°) The Wandering Peacock (°)

AlyssaRating, 5 stars1 week ago

I went for my boyfriends 25th birthday it was absolutely stunning from all of the art everywhere in the house and outside! We stayed in the sauna from when we got there till late at night it was an absolutely wonderful experience even just for a night!

Home in Stamford

4.84 out of 5 average rating, 154 reviews

Gem by the water+ firepit and all fenced backyard

TatendaRating, 5 stars1 month ago

I thoroughly enjoyed staying at Maritza’s place. She was very responsive and proactive in sending us the instructions to the house. The house was very clean and homey. The amenities were as described & it had enough space for everyone . I went with 5 other of my friends & there was enough sleeping space. The neighborhood itself is safe & we had no safety concerns. We had a wonderful stay & a wonderful host. Would definitely stay here again if ever we are back in Connecticut!

Vacation rentals for every style

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Popular amenities for Woodbridge vacation rentals

Free parking on premises

Air conditioning

Stay near Woodbridge's top sights

Edge of the Woods Market34 locals recommend

Bella's Cafe32 locals recommend

West Rock Ridge State Park19 locals recommend

Southern Connecticut State University16 locals recommend

Yale Bowl16 locals recommend

Super Stop & Shop14 locals recommend

Other great vacation rentals in Woodbridge

An expansive outdoor area showcases a heated pool surrounded by wooden decking. Sun loungers and umbrellas are arranged around the pool, with colorful seating accents visible. Pathways meander through lush greenery, integrating seating and recreational spaces within the tranquil courtyard.

Apartment in Downtown Stamford

4.83 out of 5 average rating, 6 reviews

Sunny 1BR Apartment

JoanRating, 5 stars4 months ago

Clean , modern apt. Very easy to navigate with the technology. Staff very friendly and helpful. A bit noisy on street outside with traffic. Will definitely rent again with URBY, but request a courtyard side unit

Top guest favorite

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

4.93 out of 5 average rating, 319 reviews

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars4 months ago

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

Cottage in North Fork

5 out of 5 average rating, 13 reviews

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

ChristinaRating, 5 stars2 weeks ago

Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

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

4.94 out of 5 average rating, 68 reviews

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

AdamRating, 5 stars2 weeks ago

We had a wonderful stay at the cabin. It was a perfect size for our family and our son had a great time playing in the yard and the playground right next door. Our hosts were super responsive the couple of times we needed something. We'll definitely be back!

A spacious deck features two lounge chairs and a table set against a backdrop of lush, green trees. The wooden architecture of the A-frame cabin is visible, creating a comfortable space for relaxation. Large glass doors offer access to the interior.

Cabin in New Milford

4.84 out of 5 average rating, 134 reviews

A-Frame Cottage off Candlewood Lake

SimonRating, 5 stars3 weeks ago

Super responsive, hosts. Thanks again!

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

4.95 out of 5 average rating, 19 reviews

Beach House steps from sand & Amazing Views

DonnaRating, 5 stars2 weeks ago

Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.

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

4.89 out of 5 average rating, 485 reviews

Great little place just for a couple

PaulRating, 5 stars5 days ago

The property was cozy and clean with great graden sitting are and almost everything you could need. Only qualm was that the property was advertised to have a fence but there isn’t one, there is a hedge but not a gate to make an enclosed space for a dog. This isn’t a huge deal because the beach is so close and great for walks just a minor disappoint other than that the place is incredibly cozy and we would be happy to stay here again

A charming beachside home is showcased, featuring a wrap-around porch with seating. The sandy beachfront extends along the water's edge, and a clear blue sky overhead enhances the coastal atmosphere. Nearby houses are visible, offering a sense of community along the shore.

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago

we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Quick stats about vacation rentals in Woodbridge

Total rentals
60 properties
Total number of reviews
2.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi

Frequently Asked Questions

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 20 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 house rentals in Woodbridge have free parking?
Absolutely! We offer over 20 house 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 20 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 980 vacation rentals in West Rock, over 930 vacation rentals in Westville, and over 1,010 vacation rentals in West New Haven.

Destinations to explore