Family-friendly vacation rentals in Ludlow

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Ludlow family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.
Apartment in Townshend
4.94 out of 5 average rating, 239 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars1 week ago
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!
Guest favorite
A captivating sunset paints the sky with hues of orange, pink, and purple, with rolling hills silhouetted in the foreground. The distant mountains create a serene backdrop, accentuating the natural beauty of the secluded setting.
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars3 months ago
Nice place thanks Mike
Top guest favorite
A cozy sleeping area is featured with a spacious bed adorned with soft pillows. Natural light filters through sheer curtains, illuminating warm wooden walls. A small TV and a decorative chair provide additional comfort, while a touch of greenery enhances the inviting atmosphere.
Guesthouse in Randolph
4.96 out of 5 average rating, 259 reviews

Macintosh Hill Farm

MadelynRating, 5 stars3 months ago
A wonderful ski weekend! We spent two nights and spent the day (Saturday) skiing at Killington. Quiet drive there and back so it was a perfect location to come back to a peaceful evening. Hot tub was amazing after skiing and very clean! Laura and Aaron were very helpful and let us know the conditions of the roads prior to our arrival. Flexible, kind and friendly! Would stay again for sure.
Superhost
A serene winter scene captures a two-story house blanketed in fresh snow. Flakes gently fall, creating a soft ambiance. The front yard features a large evergreen tree, while the warm glow of an interior light is visible through a window, hinting at a cozy atmosphere inside.
Home in Proctorsville
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

LilyRating, 5 stars3 months ago
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.
Superhost
A rustic living space features wooden beams and warm, ambient lighting. An antique stove serves as a focal point, surrounded by comfortable seating and a wooden table. Shelves filled with various items add character to the cozy atmosphere.
Cabin in Londonderry
4.82 out of 5 average rating, 474 reviews

Stunning Rustic Apple Barn - hot tub & sauna

MasonRating, 5 stars2 weeks ago
Absolutely great place to stay Ben was a great host and I really appreciated the way he had everything laid out and straight forward. Would absolutely go back anytime. If you want to get away for a peaceful relaxing time it can’t be beat. Cooking a great meal in the awesome kitchen then being able to relax in the hot tub
Top guest favorite
An open-concept kitchen features a central island with bar seating for two, surrounded by wooden cabinetry and ample natural light from large windows. A dining area with a table for six is visible, complemented by wooden chairs and a cozy living space in the background, showcasing a comfortable setting.
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars2 months ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Guest favorite
A warm living space is crafted with wooden paneling and large windows that provide natural light. Comfortable seating includes a leather sofa and patterned armchairs, arranged around a wooden coffee table. Soft lighting is provided by lamps, enhancing the cozy atmosphere.
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars2 months ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.
Guest favorite
A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.
Condo in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars2 months ago
Great spot near the mountain. nice community pool and hot tub.

Family- and pet-friendly home rentals

Superhost
An outdoor deck is featured, with Adirondack chairs arranged around a circular table. Lush greenery surrounds the area, and a scenic view of the Harriman Reservoir is visible in the distance under a partly cloudy sky.
Chalet in Readsboro
4.84 out of 5 average rating, 324 reviews

The King's Cottage

KorinaRating, 5 stars3 weeks ago
Nicholas and Jenna are great hosts! We were beyond lucky that they shared their home with us! The views were great, so great that we eloped here! Cute cozy home pushed off the road with a beautiful view off the back deck! We would love to back to visit!
Superhost
The kitchen features a long counter with eight red and white patterned bowls placed on plates, complemented by pendant lights above. A bookshelf with assorted books is seen in the background, alongside glass front cabinets showcasing decorative items.
Guest suite in Fairlee
4.88 out of 5 average rating, 186 reviews

Cloud 9 Private Suite Retreat

CatherineRating, 5 stars4 weeks ago
Amanda was so accommodating and flexible. It was a restful stay, and a very comfortable bed, and a nice place to work remotely on the days where I wasn’t visiting family in the area. The only thing I would say is to caution anyone who might have mobility issues as there are a few naturally uneven railroad tie steps on the way to the private entry with (no railings), which might be a good addition at some point. Also, the Jacuzzi tub/shower might be hard for some people to get in and out of and I would recommend a sturdy tubside bar. If it had a bar and a safer way in and out, I would’ve taken a Jacuzzi. There is also excellent Wi-Fi, but as the owner mentioned, cell service is difficult, but I had no problem accessing mine through my phone Wi-Fi settings. Thank you for an enjoyable stay!
Guest favorite
A cozy cabin is nestled among snow-covered trees, featuring a sloped roof blanketed in fresh snow. A woodpile is neatly stacked beside the structure, and a lightly snow-dusted wooden railing surrounds the entrance, enhancing the serene winter landscape.
Cabin in Mount Holly
4.92 out of 5 average rating, 196 reviews

Cozy Vermont Cabin near Okemo.

MarlaRating, 5 stars3 months ago
A very clean, cozy, and comfortable home! We came to ski at Okemo and were pleased that the house is only about a 10 minute drive from the resort and the town of Ludlow where there are great restaurants and shops. The living area of the home is spacious and great for hanging out - there were tons of movies on DVD and video games to enjoy. The kitchen was well-equipped and perfect for cooking meals at home. The beds were comfy. Overall a wonderful stay! We hope to be back in the future.
Guest favorite
The exterior of a rustic log cabin is displayed, featuring a metal roof and multiple windows with white trim. Snow covers the ground, enhancing the natural surroundings. A deck can be seen alongside the cabin, providing outdoor space for guests.
Cabin in West Windsor
4.96 out of 5 average rating, 143 reviews

Cowshed Cabin Farm

ScottRating, 5 stars3 weeks ago
I had a great stay! Very peaceful location. The cabin is very comfortable, spacious, and had everything I needed. I spent two of my days working from the back deck (which has been set up with some great shade and a table to work from!) and loved watching all the birds and squirrels visiting the feeder. Marty was a great host -- very friendly and available. I would definitely stay here again!
Superhost
A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.
Apartment in Saxtons River
4.83 out of 5 average rating, 185 reviews

Apartment on Main Street

CraigRating, 5 stars4 weeks ago
We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.
Guest favorite
A rustic cabin nestled in a snowy landscape, surrounded by tall evergreen trees. Hammocks are visible hanging from the porch. A dog wearing a blue jacket sits in the snow, adding a playful touch to the tranquil winter scene.
Cabin in Jamaica
4.9 out of 5 average rating, 392 reviews

Cabin 7min to Ski Stratton-Wood Stove,Views,DogsOK

BenRating, 5 stars2 weeks ago
The place was nice, very well depicted from Airbnb. Jason is very responsive and a good host!
Top guest favorite
A charming red house is set against a lush green backdrop. Large windows provide natural light and views of the surrounding trees. A wooden deck is featured at the front, leading to a beautifully maintained lawn, inviting outdoor activities.
Cabin in Hancock
4.94 out of 5 average rating, 251 reviews

Hancock hideaway

BRating, 5 stars1 month ago
We enjoyed staying in Heidi's Hancock Hideaway! We enjoyed the peaceful, quiet & comfortable place. We enjoyed taking walks, sitting on the porch during the day & star gazing at night. Kitchen had everything we needed to make & enjoy our meals. Heidi made sure we had clear directions with perfect details to arrive at the Hideaway. We even had fun staying in and doing puzzles during the rainy days. Our dog enjoyed laying in the sunshine outside & in front of the windows. Local recommendations were great.
Guest favorite
A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.
Home in Rochester
4.98 out of 5 average rating, 204 reviews

The Guest House at Sky Hollow

JasonRating, 5 stars1 month ago
This is my second time staying at one of Jess’s properties - and I’m sure it’s not my last. The property is beautiful inside and out and has everything you need. I was in town for a full week and this place was just what I needed to relax after long work days. I can’t recommend staying at one of Jess’s places enough. You won’t regret it!!

Family-friendly home rentals with a pool

Guest favorite
A serene backyard features a heated saltwater swimming pool, surrounded by lounge chairs and a safety fence. Verdant landscapes and a blue sky provide a tranquil backdrop, while a red barn is visible in the distance, adding to the rural charm.
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Guest favorite
An outdoor heated pool is surrounded by a stone patio, furnished with lounge chairs and umbrellas. Lush green grass and neatly trimmed shrubs outline the pool area, complemented by trees and well-maintained landscaping in the background.
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars3 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Guest favorite
A spacious backyard features a clear swimming pool bordered by a wooden deck. Colorful flowers accent the landscape, and sun loungers invite relaxation. The two-story residence showcases large windows, blending the indoor and outdoor environments, with an umbrella providing shade beside the pool.
Guest suite in Killington
4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

JoshRating, 5 stars2 months ago
Amazing stay. Loved how close it was to the mountain. The pool also looked amazing so sad it was winter. Definitely recommend staying there were 4 beds and can comfortably fit 5-6 people.
Guest favorite
A clear blue pool is surrounded by a sunbathing area featuring white lounge chairs. Lush greenery and trees are visible in the background, providing a natural setting. A fenced area with tall trees enhances the outdoor space for relaxation.
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 month ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favorite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars2 months ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Superhost
A clean swimming pool is framed by a white wooden fence, featuring two metallic handrails leading into the water. Nearby, several lounge chairs provide seating options. Lush greenery and trees surround the area, creating an inviting outdoor space.
Condo in Killington
4.8 out of 5 average rating, 107 reviews

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

MikeRating, 5 stars3 months ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
Superhost
An indoor swimming pool is depicted with clear blue water, featuring multiple lanes marked by buoy lines. Surrounding areas include seating and wood-paneled walls, providing a spacious and inviting atmosphere for relaxation and recreation.
Condo in Killington
4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

ZacharyRating, 5 stars3 months ago
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.
Superhost
An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.
Condo in Killington
4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars2 weeks ago
Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!

Destinations to explore