Family-friendly vacation rentals in Weston

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Popular amenities for Weston family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A narrow hallway features light wood flooring and calming grey walls. A bookshelf filled with books is positioned against one side. The kitchen area is visible at the end, complete with modern appliances and large windows allowing natural light to fill the space.
Apartment in Downtown New Haven
4.75 out of 5 average rating, 141 reviews

Luxury Penthouse Minutes to Yale

AbiolaRating, 5 stars3 weeks ago
My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.
Superhost
Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.
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
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring
4.95 out of 5 average rating, 324 reviews

Hilltop Hideaway Forest Villa on 13 acres!

RebeccaRating, 5 stars2 weeks ago
My family of 8 adults needed a place to stay near a wedding at Glynwood. This wonderful spot was minutes away from the farm and town. The number of bedrooms and bathrooms gave everyone the privacy desired while the well equipped kitchen and living rooms had plenty of space for gathering. The house and land are beautiful, including the trail. Paula was easy to communicate with and my whole family felt comfortable and happy with the spot. Highly recommend!
Guest favorite
The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.
Guesthouse in Beacon
4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

AnthonyRating, 5 stars2 weeks ago
My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.
Guest favorite
The image captures a vibrant, rustic farm house with a yellow exterior and a red barn nearby. A lush green lawn extends in front, framed by trees, while a flowering plant hangs prominently over the porch area. The gathering spaces suggest a welcoming environment.
Home in Cold Spring
4.91 out of 5 average rating, 258 reviews

1834 Farm House

MadelineRating, 5 stars1 month ago
We keep coming back to stay here because the house is so cool and has everything you could need! A great getaway outside of nyc anytime and we always recommend to others.
Superhost
An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.
Home in Philipstown
4.82 out of 5 average rating, 57 reviews

Gorgeous Garrison Gem: Pool, Sauna, Hot Tub & More

StacyRating, 5 stars1 month ago
Claudine’s place was great for a quick get away from the city. The place was cozy and spacious at the same time. The pool, hot tub and labyrinth have the property that extra special touch. Claudine herself was super responsive, friendly and helpful. Would definitely recommend
Guest favorite
An exterior view of the carriage house showcases a charming blue façade adorned with flower boxes under the windows. Lush greenery surrounds the property, while comfortable outdoor seating invites relaxation. The structure features multiple large windows that enhance the light and open feel.
Home in Englewood
4.94 out of 5 average rating, 157 reviews

Englewood NJ Country Carriage House (15 min NYC)

MohamedRating, 5 stars3 weeks ago
Rating: ⭐⭐⭐⭐⭐⭐⭐⭐⭐⭐ (10/10) Review: The house was amazing, especially the pool, sauna, and steam room. A truly exceptional experience in every detail. Thank you, Ms. Lise, for your warm hospitality!
Guest favorite
An open living area features high ceilings and large windows that bring in natural light. A sectional sofa in deep blue surrounds a vibrant orange rug, while an artwork adorns the wall. A dining area with a wooden table and chairs can be seen in the background.
Home in North Fork
4.85 out of 5 average rating, 34 reviews

North Fork True Beachfront Home

RickRating, 5 stars1 week ago
We have had several family vacations on the North Shore now, but this was beyond our expectations. Pretty much a private beach on LI Sound in your backyard. Amazing layout with a wrap around deck with three daybeds for lounging outside among the tall hardwood trees and listening to the waves. Hammocks, hot tub and sauna below with a private gym and knocked out theater setup for streaming movies. There were 5 adults and two three year olds on this trip so the 3 full baths were great. The house felt like home for 7 great days and nights. Rainy days were filled with train museums, an aquarium and butterfly gardens and a fabulous library. And the North Atlantic waves are a 25 minute drive. Oh , and everyone said the beds were super comfortable.

Family- and pet-friendly home rentals

Superhost
A light-filled living area features a comfortable sofa adorned with nautical-themed pillows. A wooden coffee table rests on a woven rug, while a stylish floor lamp and wooden chair enhance the space. The ceiling showcases exposed beams, adding character to the room.
Home in Huntington
4.85 out of 5 average rating, 295 reviews

Nautical Farm House on Working Farm with Animals

BarbaraRating, 5 stars2 weeks ago
Beautiful space both inside and outside. Location connected to the animal farm and bakery was so charming. Location was perfect for the family reunion nearby. Easy parking. Clear communication made the stay seamless.
Superhost
A cozy dining area is visible, featuring a light wood table paired with two wooden chairs. A small potted plant sits atop the table. Surrounding shelves filled with books create a warm atmosphere, with windows allowing natural light to enter.
Apartment in East Rock
4.9 out of 5 average rating, 213 reviews

On the Park: 3 RM Apt. w/kit. in historic house

kimRating, 5 stars1 month ago
Noel’s third floor apartment is light-filled, spacious, has a cute rustic vibe and is perfectly located. It’s across the street from East Rock Park (great for walks and runs) and walking distance to restaurants and an ice cream shop. The entrance to the apartment is through Noel‘s home – – no private entrance. Parking was incredibly easy—right on the street in front of the house! We enjoyed our stay very much, especially thoughtful touches like breakfast muffins and coffee. The apartment is full of interesting books and games and is very comfortable. Noel is a helpful host.
Superhost
A bright living room is presented with a red sofa adorned with patterned cushions. A small green coffee table sits in front, while a textured area rug covers the floor. Natural light streams through the window, complemented by light drapes. A wall art piece captures a street scene.
Apartment in Port Jefferson Station
4.84 out of 5 average rating, 293 reviews

The Palm Tree Extended Stay

NatashaRating, 5 stars3 weeks ago
Clean, spacious, private basement apartment with some natural light. Very comfortable bed. Lovely backyard. Quiet, green residential neighborhood. Within 10 minute driving distance from Port Jefferson town center.
Guest favorite
The exterior of a historic three-story building is visible, featuring a red brick façade adorned with lush green planters and vibrant flowers. Large windows allow natural light to enter. A welcoming entryway with a green door and potted plants enhances the inviting ambiance.
Loft in Getty Square
4.94 out of 5 average rating, 341 reviews

Blacksmith Bldg Guesthouse Upscale in downtown.

MichaelRating, 5 stars1 month ago
We had a terrific experience with Robert's apartment. The hosts were flexible, informative, and responsive. The unit was extremely clean and well appointed with little touches that we appreciated. It is in a quiet part of downtown with walkable access to the waterfront, good coffee, and excellent restaurants. If you have a reason to be in the Yonkers region I couldn't recommend it highly enough.
Top guest favorite
A charming house trailer is shown with white trim and multiple windows, surrounded by trees. An outdoor wooden deck features a grill, purple chairs, and a small pumpkin. Steps lead up to the entrance, offering access to the inviting outdoor space.
Farm stay in Fort Montgomery
4.98 out of 5 average rating, 196 reviews

Secluded overlook cottage near West Point

SarahRating, 5 stars1 week ago
Really enjoyed our stay at this peaceful farm. The location was very convenient to Bear Mountain State Park / the Appalachian Trail. The sound of the frogs at the nearby pond and the friendly horses really make this place a gem. Would highly recommend for a relaxing getaway!
Top guest favorite
A view of Long Island Sound at sunset is captured from the balcony. Gentle waves reflect the colors of the sky, ranging from soft pink to deep orange, while Charles Island is visible in the distance, framed by the serene horizon.
Home in Milford
5 out of 5 average rating, 103 reviews

Milford Beach House - Newer Construction!

SabrinaRating, 5 stars3 weeks ago
Victor and Kim were gracious and amazing hosts. I was celebrating my birthday and they even had a card, a bottle of champagne, red wine and fruit. It was such a wonderful surprise! The house was so beautiful and the beach is just outside! The kitchen was fully stocked with everything one would need to cook for a family; there was a convection oven! We loved using the grill as it was memorial day. Bathrooms had rain showers. Beds were so comfortable and it was truly wonderful to wake up to a beautiful sunrise and to just listen to the waves from the deck or even the living room. We spent a lot of time outside, on the beach. It was home away from home.
Guest favorite
A welcoming living area features a spacious sectional sofa adorned with accent pillows. A coffee table with a glass top, displaying a small vase of flowers, sits in the center. Light filters in through sliding glass doors, illuminating the wood-like flooring.
Apartment in Carmel-by-the-Sea
4.87 out of 5 average rating, 300 reviews

Private space, with yard

EveRating, 5 stars6 days ago
Skye was really helpful and always responded quickly. This is a private location but if you're looking for stuff to do, Carmel is a short drive to Beacon and Cold Spring. It is very pretty in this area and very woodsy. The space is in the lower level and cool and opens to a private yard with seating.
Top guest favorite
A vintage Airstream camper is nestled among vibrant autumn foliage, featuring shades of red and yellow. Surrounding the camper are rugged stones and a rustic outdoor seating area. The ground is covered in fallen leaves, enhancing the natural ambiance of the wooded setting.
Camper/RV in Cold Spring
4.95 out of 5 average rating, 534 reviews

Hudson Highlands Base Camp

SarahRating, 5 stars2 weeks ago
We really enjoyed our stay! The Airstream matched the photos and listing perfectly and is tucked in a quiet, wooded location. We were able to walk to the restaurants, small shops and the train station. Highly recommend this spot for anyone craving the nostalgia of 80s camping.

Family-friendly home rentals with a pool

Top guest favorite
A spacious outdoor area features a rectangular swimming pool with a set of steps leading into the water. The pool is surrounded by a sunbathing deck and landscaped gardens. The back of the house includes large windows allowing for ample natural light.
Apartment in Redding
5 out of 5 average rating, 17 reviews

Poolside apartment with private tennis court.

MauroofRating, 5 stars12 months ago
We had a wonderful stay at Todd's place! Todd greeted us warmly and was very responsive. The pool was fantastic and surrounded by beautiful nature, making it a serene spot to relax. We stayed in the pool apartment, which looked out at the pool and stunning backyard. It was well-equipped with a kitchen, pool towels, a TV, couches, and a dining table. Wendy, Todd's wife, welcomed us with cookies, and they provided milk, orange juice, eggs, yogurt, and fruits. There was also a grill available. We stayed for three nights and enjoyed the pool a lot. Despite being a shared pool, there was plenty of space and time for everyone. We also used the tennis court and played some basketball at the basketball rink there. Todd and Wendy made our stay very comfortable and enjoyable. We highly recommend their place!
Superhost
A spacious living area features two leather sofas positioned around a central coffee table. Natural light enters through three windows, illuminating built-in shelves filled with books and decorative items. An entertainment unit with a television is present, along with a lamp providing additional lighting.
Apartment in Huntington
4.64 out of 5 average rating, 198 reviews

"House of Tranquility!" Private Apt., Great Area!

JasonRating, 5 stars2 weeks ago
Rob’s place is very comfy with all the little things you could wish for. He even left snacks. The downstairs apartment is very private. His description was very accurate, with a mild smell of mold that clear out after starting the AC and air filter. I’m allergic to mold and had no problems. I would gladly stay again.
Top guest favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
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
Two people are seen swimming in a calm body of water, surrounded by gentle ripples reflecting sunlight. Lush greenery lines the distant shoreline, creating a serene backdrop against the shimmering surface.
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.
Home in Philipstown
5 out of 5 average rating, 9 reviews

Arkadia House Mid-century retreat with pool & view

AriRating, 5 stars71 months ago
Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.
Top guest favorite
Home in Lagrangeville
5 out of 5 average rating, 34 reviews

Hudson Valley Colonial with Inground Pool

ChelseaRating, 5 stars1 week ago
Kathleens place was perfect for our friends and family weekend vacation upstate. The house and property was absolutely stunning and fit our group of 10 so comfortably. We were talking about our next stay there before we even left. Highly recommend!
Guest favorite
A serene salt-water pool reflects the surrounding greenery and blue sky. The natural stone edge frames the pool, while two lounge chairs are positioned nearby, creating a peaceful outdoor retreat.
Home in Cold Spring
4.95 out of 5 average rating, 170 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

AndyRating, 5 stars1 month ago
It was comfortable, very roomy, and cozy. There was good shared space and good privacy. The grounds were lovely, there was a great pool, and it was very convenient to so many good things to do in the area. It's one of our favorite rentals to date!

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$20,931 GYD before taxes and fees

  • Total number of reviews

    340 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore