Kid-friendly vacation rentals in Monterey

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Popular amenities for Monterey kid-friendly rentals

Kid-friendly house rentals

Guest favorite
A charming house is set within a wooded area, with autumn foliage creating a colorful backdrop. The exterior features a stone fireplace and expansive windows, offering glimpses of the serene environment. Nearby, a fire pit with seating is positioned on the green lawn.
Home in Becket
4.93 out of 5 average rating, 116 reviews

Beautiful, quiet and cozy home in Becket!

AndrewRating, 5 stars1 month ago
My wife and I stayed here 2 night with our dog and had a great time. The cabin was super cozy and had everything we needed during our stay. Special shoutout to the couch, which was extremely comfortable for late night movie watching! If you are looking for a quiet weekend away to do some hiking, I would certainly recommend staying here. The town of Becket is very rural and food options can be somewhat limited but the house has a full kitchen and grill to use if that's more your style. Overall 5 stars would stay here again.
Top guest favorite
A spacious kitchen features dark cabinetry paired with granite countertops, offering ample workspace. Appliances include a large gas range and dual ovens. Natural light fills the area through sliding glass doors leading to the outdoor deck. A colorful floral rug adds a welcoming touch.
Home in Monterey
5 out of 5 average rating, 21 reviews

Berkshires Retreat | Fenced Yard + Near Tanglewood

CharmaineRating, 5 stars2 months ago
Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.
Guest favorite
A bright living room features large windows that provide natural light and views of trees outside. Comfortable seating includes a leather sofa and a light-colored couch adorned with colorful cushions. A coffee table sits centrally on a patterned rug, complemented by two woven chairs.
Home in Monterey
4.97 out of 5 average rating, 34 reviews

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

GallianeRating, 5 stars3 months ago
This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.
Superhost
A modern living room features a large, plush sectional sofa adorned with soft white throws. Natural light floods in through expansive windows, showcasing a beautiful view of the lake. A stone fireplace adds charm, while a television is mounted above, providing entertainment.
Home in Monterey
4.88 out of 5 average rating, 8 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars4 months ago
This house was great for a winter weekend getaway! Great Barrington, Lenox, and Stockbridge are all adorable towns to visit and are a 15 - 30m drive away. The house itself was cozy and had all the amenities we needed. Shay was very responsive. Something to know about the area is that ride shares and cabs are hard to come by, so having a car that fit everyone we were traveling with was crucial for our group to get around town.
Top guest favorite
Home in Egremont
4.98 out of 5 average rating, 136 reviews

A sunny, quiet chalet beautifully decorated.

CrystalRating, 5 stars2 weeks ago
Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.
Top guest favorite
A charming red house is surrounded by lush greenery and colorful flower beds. The well-maintained lawn features a variety of blooming plants, enhancing the home's inviting exterior. The building's porch, framed by vibrant flowers, offers a welcoming entrance.
Home in Great Barrington
4.98 out of 5 average rating, 114 reviews

Prime location for the best of the Berkshires

ChadRating, 5 stars3 months ago
Marty’s cabin is perfect for a Great Barrington getaway. We stayed in the cabin for a ski weekend, and it simply met all our expectations and then some. The cabin was kept extremely clean and had a ton of extras (board games, coffee, filtered water, etc.) that added a great touch. Location was perfect for a day at butternut mountain. Highly recommend, and will definitely go back next year. Thank you!
Guest favorite
A light-filled bedroom features a white bed with plush bedding, complemented by two windows covered with dark blinds. A small nightstand holds a lamp, and a wooden chair adds to the decor. The walls are adorned with framed photographs.
Home in Sheffield
4.95 out of 5 average rating, 100 reviews

Great Berkshire Getaway !

JonRating, 5 stars1 month ago
Cute place with a great location. It’s right down the street from Berkshires. Host is great too. Good communication throughout the stay.
Guest favorite
A living area features natural wood beams overhead and large windows allowing for ample natural light. A comfortable gray sectional sofa is paired with a cozy area rug. A wood-burning stove is positioned against the wall, adding warmth to the space.
Home in New Marlborough
4.86 out of 5 average rating, 7 reviews

Biggest Tiny Birdwatcher's Paradise

JenniferRating, 5 stars2 months ago
We really enjoyed our long weekend at Jake’s rental. I love the aesthetic of the space. It was very comfortable for myself, my husband and our mini Aussie dog. It is a quick drive to Great Barrington. We loved Mooncloud which features interesting cocktails and charcuterie. Down the street from the house is access to the Appalachian Trail. It was an easy drive to Pittsfield for my brother’s birthday. Would love to come again!

Kid-friendly apartment rentals

Guest favorite
A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.
Apartment in Amenia
4.92 out of 5 average rating, 105 reviews

Amenia Main St Cozy Studio

AvocetRating, 5 stars3 weeks ago
Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.
Superhost
A small galley kitchen features wooden cabinets and open shelving, displaying various kitchenware. A white stove and microwave are on the counter, while a laundry area is visible through an open doorway. Natural light enters from a nearby window, illuminating the rustic wood flooring.
Apartment in Chester
4.77 out of 5 average rating, 202 reviews

Quiet getaway in the Berkshires

GailRating, 5 stars3 weeks ago
Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy
Top guest favorite
A red barn-style building is illuminated at night, featuring two large garage doors at ground level and two windows above. The light from the windows hints at the warm interior, while the surrounding area remains dark, creating a serene and inviting ambiance.
Apartment in Sheffield
4.93 out of 5 average rating, 150 reviews

Private Berkshire Barn Apartment

HelenRating, 5 stars3 weeks ago
Just perfect: cozy, inviting, private. Everything you need, with lots of personal touches. We had a wonderful time!
Top guest favorite
A tranquil sleeping area features a wooden bed topped with a vibrant patterned quilt. Natural light enters through a window, illuminating the space. A wooden cabinet and a side table with a lamp add functionality, complemented by artwork on the walls showcasing nature scenes.
Apartment in East Chatham
4.95 out of 5 average rating, 120 reviews

Bennett Abode

AmandaRating, 5 stars3 days ago
We thoroughly enjoyed our stay at the Bennett’s Abode! Larry and Lana’s airbnb had just about everything a visitor would need and they even included a detailed binder full of information and ideas pertaining to the area. Larry was so prompt with his responses and always kept us in the loop. He even provided several great hiking ideas that we utilized throughout our stay at his home. We were so grateful for the overall experience and left with incredible memories!
Top guest favorite
A wooden structure with a deck extends into the greenery, framed by tall hop poles. The building features a large front porch, inviting outdoor seating, and an entrance accentuated by surrounding trees and a grassy area leading up to it.
Apartment in Petersburgh
4.88 out of 5 average rating, 184 reviews

The Beer Diviner Brewery Apartment

HeidiRating, 5 stars1 week ago
Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!
Top guest favorite
A spacious studio apartment is displayed with natural light streaming through large windows. A comfortable narrow futon and a cozy seating area are visible, along with a dining table surrounded by wooden chairs. A door leads to the private deck, enhancing the overall openness.
Apartment in Sandisfield
4.92 out of 5 average rating, 235 reviews

Sunny Berkshire Studio Apartment

AntonRating, 5 stars9 months ago
Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again
Top guest favorite
An open studio layout features a sleeping area with a spacious bed and a colorful area rug. A wooden loft with stairs for access is visible in the background. Bathroom and kitchen areas are partially seen, providing convenience and functionality.
Apartment in Troy
4.93 out of 5 average rating, 440 reviews

Stunning studio in the heart of Troy: Raven's Den

BobRating, 5 stars1 week ago
Perfect night for a nearby getaway while things done at my apartment. Lot of charm and everything you could need is in this den. Pictures did it justice. I’ll stay again just for the fun of it next time. Igor was easy to communicate with and he was spot on with everything he has posted on the listing. This place is a gem!
Guest favorite
A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.
Apartment in Copake Falls
4.91 out of 5 average rating, 331 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

TimRating, 5 stars2 weeks ago
My wife, dog, and I had a wonderful and peaceful stay at Michael's place. The land is beautiful, the place itself is actually even nicer than the pictures, and there is plenty to do in the area. We will definitely be coming back!

Kid-friendly condo rentals

Guest favorite
A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.
Condo in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars5 months ago
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!
Top guest favorite
A spacious living area is highlighted by two large windows allowing natural light to fill the room. A dark leather sofa is paired with a wooden coffee table and a patterned area rug. A dining table made of wood is positioned nearby, alongside a console table with decorative items.
Condo in Downtown Hartford
4.99 out of 5 average rating, 126 reviews

Posh Pad in The Business District

KimberlyRating, 5 stars2 weeks ago
We loved our stay at Obi’s apartment in Hartford. It was spacious and comfortable for our family of 4. Street parking was easy. Obi is a great host! We’d love to stay here again the next time we’re in the area.
Guest favorite
A dining area features a light-colored table with four wooden chairs, complemented by a decorative fruit bowl. Exposed brick walls add character, while soft lighting from nearby lamps creates a bright and inviting atmosphere. A comfortable living space is also visible in the background.
Condo in Lenox
4.97 out of 5 average rating, 34 reviews

Spacious 3 bedroom apt in Lenox historic downtown

JamieRating, 5 stars2 weeks ago
Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!
Superhost
A cozy living area features a grey sofa, complemented by a vibrant orange armchair. Colorful artwork adorns the wall above, enhanced by two stylish lamps casting warm light. A sleek coffee table sits between the seating, inviting relaxation and conversation.
Condo in New Britain
4.82 out of 5 average rating, 126 reviews

New Britain "Joy of Small Space" Condo

AdamRating, 5 stars1 week ago
Muna was incredible start to finish with my stay. Helpful, communicative and accommodating. Place was perfectly as described. Genuinely recommend a stay at her place!
Guest favorite
A spacious living area is adorned with a large area rug and a comfortable blue bed. Large windows allow natural light to illuminate the room, highlighting the warm yellow walls and the vintage chandelier. A small coffee table and plush seating invite relaxation.
Condo in Albany
4.9 out of 5 average rating, 267 reviews

Elegant, spacious studio apt in historic mansion

LindseyRating, 5 stars1 week ago
Such a unique stay! David gave very helpful instructions for arriving and getting to the property, even supplied photos for extra assistance. The property itself is cozy and in a great part of the city. There’s lots to do nearby, super walkable, and David provides great local recommendations. The shared gallery space was so cool to see too. Great experience!
Superhost
A well-lit bedroom features a spacious bed with white linens and an accent pillow. Bright light streams in through two windows adorned with sheer curtains. A side table with a small lamp adds a touch of warmth to the inviting space.
Condo in Kingston
4.91 out of 5 average rating, 144 reviews

Cozy & walking distance to cafés *spring avails*

JananiRating, 5 stars2 months ago
Cozy apartment, walking distance from the water front. Had a great weekend getaway.
Top guest favorite
The exterior of the residence features a two-story wooden structure with stairs leading to an upper-level entry. Natural stone accents and a landscaped area with gravel and trees contribute to the overall aesthetic. Nearby outdoor seating is partially visible in the background.
Condo in Northampton
4.97 out of 5 average rating, 63 reviews

Lovely 1bedrom apartment with screened in porch

LauraRating, 5 stars3 weeks ago
Beautiful and very clean space! We had the most wonderful long weekend at Goran's apartment. He was so responsive and super friendly... cannot recommend enough. We will be back!
Guest favorite
A street view showcases a charming area in North Adams, featuring several historic buildings with unique architecture. Prominent spires rise above the rooftops, framed by rolling hills in the background, while a clear blue sky enhances the vibrant environment.
Condo in North Adams
4.89 out of 5 average rating, 28 reviews

Downtown Condo - walk to MoCA

RuthRating, 5 stars1 week ago
My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

Quick stats about vacation rentals that are kid-friendly in Monterey

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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