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Family-friendly vacation rentals in Holden

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Holden family-friendly rentals

Family-friendly home rentals with a hot tub

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars40 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Guest favorite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars6 days ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Superhost
Cottage in Westford
4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago
We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙
Guest favorite
Home in Ashford
4.87 out of 5 average rating, 78 reviews

Large secluded house in the Woods; Pool, hot tub!

TalRating, 5 stars8 months ago
We came as a group of friends with a baby to stay at Blake and Tracy's house, and we had a great stay. They were very communicative and accommodated all our requests to ensure our stay was excellent. They asked in advance if it would be okay for their child to stay in his room inside the house, and we agreed. We didn’t see him at all during our stay, and it didn’t disturb us in the slightest. The fact that Blake and Tracy live right next door was convenient, as they were readily available for anything we needed, but we never felt their presence. We will definitely come back!
Guest favorite
Apartment in Holliston
4.96 out of 5 average rating, 120 reviews

Lake Link

JordanRating, 5 stars6 months ago
We spent a couple of months at Loch Link while our home (a couple of towns over) was being renovated. Mike and Erica were helpful throughout the process and did their best to make us feel like we had a home away from home. It was a hectic change to our schedules, especially with 2 young kids, but we were grateful to have excellent hosts and a cozy place to stay. We moved a lot from our home that we ended up bringing back, because the rental already had most of what we needed. The weather only allowed us a few swims in the pool but it was definitely a hit with the kids.

Family- and pet-friendly home rentals

Guest favorite
Townhouse in Allston
4.93 out of 5 average rating, 186 reviews

Sparkling Condo With Modern Amenities

AllisonRating, 5 stars8 months ago
Michelle was very responsive and great at communicating leading up to our stay. The house was easy to find, good neighborhood, perfectly clean and had everything we needed. Parking was included which was awesome. The T was easy to walk to so we could go downtown every day easily. The host recommendation for Lulu’s Allston was spot on, it was nearby and great. We felt right at home and had a wonderful stay and check out was also easy. Thank you Michelle for hosting a wonderful place!
Guest favorite
Guest suite in Charlton
4.86 out of 5 average rating, 410 reviews

Baker Pond Hideaway

MarcyRating, 5 stars2 months ago
Best vacation we’ve had in months! Kathleen and Mike are one of the most amazing hosts we’ve met! So kind and thoughtful, with perfect balance of being attentive and giving us space to venture on our own for duration of stay! They went above and beyond to make our stay comfortable! It’s such a peaceful and cozy spot, we can’t wait to go back! Our two pups had a great time too, exploring and roaming. If you’re in need of a quiet, relaxing get-away that’s pet-friendly this is the perfect place!
Top guest favorite
Apartment in Concord
4.96 out of 5 average rating, 206 reviews

Mema's Place --Lovely apartment in private home

DarleneRating, 5 stars1 week ago
Wonderful and serene place to stay. Lots of room, clean, perfect for two and a puppy. Would definitely recommend.
Guest favorite
Farm stay in Southbridge
4.89 out of 5 average rating, 327 reviews

Scandanavian Wigwam with Sauna and Forest Baths

ChristinaRating, 5 stars1 month ago
Yet again, this place does not disappoint. This was my fourth time staying at the wigwam in as many years - there's a reason I keep coming back! This land definitely has magic in it and I can always count on feeling refreshed and revived after my stay (and with several new poems!). As always, the forest bath and sauna are the perfect piece of luxury while "roughing it." This will always be one of my happiest places ❤️
Top guest favorite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.
Guest favorite
Home in Coolidge Corner
4.78 out of 5 average rating, 114 reviews

Lovely sunny 2 BD home, great area. Free Parking

MichelleRating, 5 stars2 months ago
Wendy’s home served as a home away from home as we were in town to meet our new grandchild. The home is the downstairs unit of a 2 unit residence. Easy access to dining, shopping, local parks. The home itself is warm, comfortable, well-stocked with linens, kitchen items, etc. Coffee press and kettle. The sunroom was my favorite spot in the house. Great light throughout the day, warmed by a radiator and a comfy chair with ottoman and blanket. I highly recommend this beautiful home for any stay in the Brookline area. Thank you, Wendy!
Guest favorite
Cottage in Hollis
4.88 out of 5 average rating, 238 reviews

Lakefront Nature Getaway - Wood fired Cedar Sauna

LaurieRating, 5 stars1 month ago
We greatly enjoyed this relaxing retreat on scenic Silver Lake while visiting our family. The kitchen was well stocked for cooking and Eric was an excellent host with great communication and recommendations for local music. He did a super job with keeping the walkways and driveway free of winter snow and ice with challenging weather conditions. We loved the location that was 20 minutes from the Westwood YMCA and close to Hollis markets and restaurants. We especially appreciated the old fashioned Country Store Ace Hardware and Toy Store in nearby Milford.
Guest favorite
Cottage in Bernardston
4.88 out of 5 average rating, 315 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

NorrieRating, 5 stars4 months ago
This is my second Christmas staying at Chris’s place. I really enjoy this cozy cottage. I spend time with my family, Bella plays with their dogs, and then we have our own special place to go home too. Bella really enjoys the outside, I very much enjoy the inside! Thank you so much for taking good care of us. See you next year. 🤞

Family-friendly home rentals with a pool

Top guest favorite
Farm stay in Rutland
4.96 out of 5 average rating, 363 reviews

Farm Living

GinaRating, 5 stars2 weeks ago
This was a wonderful stay for myself, daughter and two rambunctious grandsons. We all loved the farm experience and enjoyed visiting the animals... peacock, rabbitts, chickens galore, ducks, goats, donkeys, horses and cows! The trampoline and two playstructures plus sand box were fantastic! The hosts, Roger and Melissa, were very welcoming and encouraged us to explore. Having the farm store right on the property was a bonus!
Top guest favorite
Townhouse in Groton
5 out of 5 average rating, 77 reviews

Potager Farm Private Townhouse

AnnieRating, 5 stars2 months ago
This was my second time staying here and it was every bit as perfect as my first stay! Christine's place is incredibly comfortable, clean, spacious and beautiful. Highly recommended!
Guest favorite
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars1 month ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Guest favorite
Home in Brimfield
4.88 out of 5 average rating, 72 reviews

Luxury Home * Pool * Fireplace

DanaRating, 5 stars3 months ago
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 before taxes and fees

  • Total number of reviews

    490 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore