Family-friendly vacation rentals in Woodbridge

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Popular amenities for Woodbridge family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Washington
4.81 out of 5 average rating, 21 reviews

ZoomIn Map BestTown Washington "Kirby" PoshPadsCT

ElizabethRating, 5 stars12 months ago
Beautiful house, gorgeous and convenient location, excellent host. We had a great stay.
Top guest favorite
Home in North Fork
4.97 out of 5 average rating, 206 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars4 weeks ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Guest favorite
Home in North Fork
4.9 out of 5 average rating, 21 reviews

Chic Beach House: Waterfront, Vineyards, Hot Tub

SamRating, 5 stars2 months ago
Our family rented for a weekend off season. Surroundings were beautiful. Home was clean and comfortable. Host was super friendly and very communicative. Any questions were answered within 5-10 minutes. Lots and lots of space for large groups. We had 6 adults, 2 children and a dog in our trip. Literally open the back door and you’re right on the beautiful beach!
Guest favorite
Home in Litchfield
4.96 out of 5 average rating, 95 reviews

Home in historic Litchfield village

JessicaRating, 5 stars7 months ago
Jeannine’s home was an absolute gem! We had our annual girls weekend here and felt right at home. The house was so cozy and warm yet had ample space for me and the girls to sit and chat together. We loved that the house was lived in with family photos and mementos around, rather than being sterile like many other bnbs we’ve stayed in. There was also so much to do in the surrounding area! I would definitely recommend this stay :)
Top guest favorite
Home in Wading River
4.96 out of 5 average rating, 504 reviews

Your Zen Retreat

ChrisRating, 5 stars1 week ago
We had an event nearby and Brian’s place was a great base for us. Lovely and peaceful neighborhood. Brian was super responsive and reached out to us when the house was ready(before the official check-in time). Would def recommend to anyone!
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 116 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars2 months ago
Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!
Guest favorite
Farm stay in Kent
4.86 out of 5 average rating, 318 reviews

(°) The Wandering Peacock (°)

SarahRating, 5 stars2 weeks ago
We only stayed at the Wandering Peacock for 1 night but it was such a treat as a place to crash along our road trip. Not a corner of the home was glossed over, every inch of the place is beautifully curated. Abigail was super responsive and a welcoming host. We squeezed in some time for the hot tub, it was ready to go in 2-3 hours and super relaxing. 10/10 would recommend.
Apartment in Shelton
4.68 out of 5 average rating, 325 reviews

1ST FLR APT Your private resort, now FAMILY-ized!

OrlandoRating, 5 stars3 weeks ago
We had a wonderful stay! Gabe was a very welcoming host and shared some great local restaurant recommendations—highly recommend checking out Casa Nova on River Road. His two dogs, Molly and Nate, were also incredibly friendly and added a warm, homey touch to the experience. The apartment was spotless and filled with thoughtful notes that made everything easy. A special surprise was the bag of everything needed to make s’mores left for us—such a sweet and thoughtful gesture! The pool area offered stunning views, and the hot tub was clean and perfect for relaxing. There’s even a hiking trail accessible right from the property, which we unfortunately didn’t get a chance to explore—but it’s a great bonus for future visits. This place truly felt like a little piece of heaven. We’d absolutely stay here again!

Family- and pet-friendly home rentals

Guest favorite
Cottage in Middlefield
4.92 out of 5 average rating, 247 reviews

Lake Beseck cottage

MaryRating, 5 stars2 weeks ago
We loved our stay here. It was the perfect place for two of us and our dog. The home was just as described, welcoming, cosy and well equipped, and we appreciated all the local recommendations. We enjoyed local walks, the lake, and the great dog park, as well as easy access to Middletown to visit our son. Elisabeth and Daniel were fantastic hosts!
Guest favorite
Cottage in North Fork
4.97 out of 5 average rating, 154 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

BrettRating, 5 stars1 week ago
Look no further! The Beach Cottage is beautiful, immaculate, private, and all things one would hope a vacation getaway would entail. This location feels “off the grid” albeit close to modern amenities/stores. Hope to be back soon!
Top guest favorite
Guesthouse in South Salem
4.94 out of 5 average rating, 283 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

AlicjaRating, 5 stars1 month ago
We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!
Superhost
Cabin in New Milford
4.84 out of 5 average rating, 136 reviews

A-Frame Cottage off Candlewood Lake

PaulRating, 5 stars1 month ago
Emily and Carol were wonderful hosts. They were responsive to our questions and provided great recommendations. Sitting on the balcony with the view of the trees and the lake beyond was tranquil. The living area is cozily furnished and both the fireplace and tv were easy to use. The nearby community beach was fun to visit and an added benefit of the stay. Great location with plenty of good food and small town charm!
Guest favorite
Cottage in Guilford
4.93 out of 5 average rating, 273 reviews

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

MaryRating, 5 stars2 weeks ago
Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.
Top guest favorite
Cottage in Fairfield
4.98 out of 5 average rating, 120 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

BriannaRating, 5 stars9 months ago
We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.
Guest favorite
Guest suite in North Fork
4.88 out of 5 average rating, 665 reviews

Walk to Vineyards, Beaches, Farms & Town

DoreenRating, 5 stars4 weeks ago
We spent a special weekend at Alex’s place to celebrate our 33rd wedding anniversary — and it was also our dog’s very first trip with us! As new dog parents, we couldn’t have asked for a better spot. The home was peaceful, dog-friendly, and just what we needed to unwind. The bed was incredibly comfortable, and everything was clean and well-appointed. We truly enjoyed our stay and would absolutely recommend it to others.
Top guest favorite
Guesthouse in Southport
4.96 out of 5 average rating, 194 reviews

Southport, CT across from BEACH

ValRating, 5 stars1 week ago
Jeff’s place was a hidden gem. It was private, close to the beach and town and the home was safe, clean and well designed. Jeff was kind and super responsive. There is a reason this place is always booked. I highly recommend staying here and can’t wait to return!

Family-friendly home rentals with a pool

Top guest favorite
Barn in Bethel
4.98 out of 5 average rating, 237 reviews

Escape to a Restored New England Antique Milk Barn

GavinRating, 5 stars2 weeks ago
My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.
Guest favorite
Home in North Fork
4.87 out of 5 average rating, 127 reviews

The Perfect North Fork Escape

JodieRating, 5 stars2 weeks ago
Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.
Home in North Fork
4.8 out of 5 average rating, 5 reviews

NoFo Getaway: Pool, Farm Views, Beach Sunsets

LylyRating, 5 stars2 months ago
This was the perfect place for our family to get away from the city. It was a family friendly home that was perfect for our little one. The house was clean and came with all of the necessary essentials we needed. The location was private and serene while still accessible to lots of wonderful local restaurants and stores. The beach was easily accessible and within walking distance. Additionally, Morgan was responsive and always available to answer any questions we had. We absolutely enjoyed our stay and recommend it to any family.
Superhost
Condo in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

DenisRating, 5 stars6 months ago
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!
Guest favorite
Cottage in Redding
4.96 out of 5 average rating, 23 reviews

Guesthouse & private pool, historic 24-acre estate

IanRating, 5 stars9 months ago
This place really is a gem. The bedroom and bathroom and spacious and have everything you need. The kitchen is small and can be challenging to work in, but the outdoor grill and dining space make up for that. We spent most of our time outside by the private pool relaxing. James and Margie were great hosts. They greeted us upon arrival and were so friendly and warm. They even brought fresh-bakes cookies. We had a great time!
Guest favorite
Condo in Mount Sinai
5 out of 5 average rating, 34 reviews

1856 Trading House close to water

JohnRating, 5 stars5 months ago
Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars1 week ago
Only complaint would be the noise from road during the morning commute
Guest favorite
Apartment in Glastonbury
4.89 out of 5 average rating, 438 reviews

Quiet 2 bed room apt w/ private entrance.

JoshRating, 5 stars3 weeks ago
Alice’s place was great! We’ll be back again for sure.

Quick stats about vacation rentals that are family-friendly in Woodbridge

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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