
Family-friendly holiday rentals in Woodbridge
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Woodbridge
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Guesthouse Farm Stay
Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

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.

New Haven Pizza Cozy Guest House 1 mile to yale
Welcome to our 2 bedroom 1 bathroom peaceful and centrally-located guest house. Located in the heart of New Haven less than 5 min away from Yale Hospital and less than 10 minutes from Yale University. The unit has some amazing features like a private 1 car parking space and in-unit washer and dryer. The space is cozy, but has all the necessary amenities for a comfortable short or long stay. Full size kitchen appliances, large bathroom with glass shower & central AC. All pizza lovers welcome

2 Bedroom with sweeping views of Long Island Sound
Entire 1st floor apartment with private entrance. A spacious layout with spectacular views of Long Island Sound from your private deck. Convenient location; minutes to downtown Milford, train station, beaches, restaurants, and shopping. 15 minutes to Yale and famous New Haven landmarks. Walking distance to local restaurants, beaches, and an ocean-side playground. Public Beach: 7 minute walk - 0.4 mi Restaurants: 6 minute walk - 0.3 mi Playground: 2 minute walk - 250' *NO SMOKING*

Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

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.

Luxurious 2BR - 2Bath W/ Gym | Downtown at Yale
Located in a brand-new luxury building, at the center of New Haven’s historic downtown, this luxury apartment provides unparalleled comfort, service, and amenities. Watch a movie on a 4K TV, relax in a living room with floor-to-ceiling windows, or whip up dinner in a fully-equipped kitchen. Highlights: • Walkable access to Yale • Deep-clean + sanitizing prior to every guest • Coffee, fresh linens, and bathroom essentials provided • 1000+ sqft private apt

Square6ix Stylish Guesthouse in Westville
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.

Wintergreen Gardens Suite @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

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!

Rustic Two-Story Townhouse Apartment
Rustic two-story Townhouse Apartment connected to Historic New England home located in downtown New Haven. Although the unit is connected to the main house it has its own entrance, kitchen, living room, bedroom and bathroom. It is connected to the main house through a staircase to the basement and a French door. Please note: We have a family cat named Jazz who likes to roam the whole house.
Popular amenities for Woodbridge family-friendly rentals
Family-friendly home rentals with a hot tub

Lakefront Bungalow Bliss | Serene 2BR Retreat

Cozy New England Escape with relaxing hot tub

Luxury cottage by the sea with hot tub and pool

Oceanfront Beach House w/ Private Hot Tub

Private cozy getaway

Cozy Cottage |Quintessential CT | Pet Friendly

Beach Haven - waterfront, near Yale, sunsets

3 Bedroom Beach House with Hot Tub!
Family- and pet-friendly home rentals

Everything you need! Full Apartment!

Luxury Stay in Expansive Historical Home

Spring Sale! Cozy Bungalow/Pet-friendly/Walk2Beach

Modern Downtown Yale, Wooster Square apartment

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

Light and airy, pet friendly rental in Newtown

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

The Cottage at Cedar Spring Farm
Family-friendly home rentals with a pool

Artist Retreat in Beautiful Country Setting

Escape to a Restored New England Antique Milk Barn

Hilltop House w/POOL/SPA- HOST & Co.

Redding Retreat with Pool

Cozy studio unit

Spacious Cottage Loft

Modern farmhouse w/ pool, beach, horses and winery

Peaceful apartment on 3.5 acres w/ Artist studio.
Quick stats about holiday rentals that are family-friendly in Woodbridge

Total holiday rentals
Explore 30 holiday rentals in Woodbridge

Nightly prices starting at
Woodbridge holiday rentals start at $102 SGD per night before taxes and fees

Verified guest reviews
Over 1,710 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Woodbridge holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Woodbridge rentals

4.6 Average rating
Woodbridge stays receive an average rating of 4.6 out of 5 from guests
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- Family-friendly rentals Connecticut
- Family-friendly rentals United States
- Yale University
- Fairfield Beach
- Thunder Ridge Ski Area
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- Kent Falls State Park
- Mohawk Mountain Ski Area
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- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
- Mount Southington Ski Area
- Yale University Art Gallery
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