Family-friendly holiday rentals in Whitingham

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Whitingham family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favourite
Home in Colrain
4.94 out of 5 average rating, 176 reviews

Secluded Farmhouse Retreat - stunning views

SophonRating, 5 stars1 week ago
This was a great home away from home. Wish it didn’t rain as much as it did. We really wanted to walk the grounds more. Inside was cozy and warm. Anything you needed it was there. Definitely thinking about coming back in the winter because it would be a perfect winter wonderland. Thanks again Sophon
Guest favourite
Farm stay in Valley Falls
4.89 out of 5 average rating, 223 reviews

Country Getaway Lodge / Ranch

TrevorRating, 5 stars4 months ago
Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.
Guest favourite
Chalet in Ludlow
4.94 out of 5 average rating, 126 reviews

Okemo Ski Chalet with Hot Tub

KatieRating, 5 stars1 month ago
Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!
Superhost
Home in Northampton
4.88 out of 5 average rating, 632 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

KatherineRating, 5 stars1 month ago
A peaceful location with chill activities for all ages...we enjoyed the phonograph, the retro Atari, the hot tub, the window bird feeder, and watching birds in the spacious yard and conservation area. Herons, hawks, and songbirds viewed. The hot tub was sparkling clean, and the linen robes were a thoughtful touch. Wifi worked great. We arrived late but instructions for entry were crystal clear. Virginia answered my questions promptly and warmly. Definitely a winner.
Superhost
Farm stay in Londonderry
4.82 out of 5 average rating, 136 reviews

Cozy Award Winning Farmhouse - hot tub and sauna!

JumanaRating, 5 stars12 months ago
Very beautiful home and lovely host! Would recommend!
Top guest favourite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars1 month 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 favourite
Flat in Londonderry
4.96 out of 5 average rating, 580 reviews

Vermont Getaway Apartment

JoshuaRating, 5 stars1 month ago
This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!
Superhost
Home in Argyle
4.83 out of 5 average rating, 150 reviews

Expansive Lakehouse with Jacuzzi

MeghanRating, 5 stars8 months ago
My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!

Family- and pet-friendly home rentals

Superhost
Farm stay in West Brattleboro
4.94 out of 5 average rating, 132 reviews

Lilac Ridge Farm House

MatthewRating, 5 stars4 months ago
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!
Guest favourite
Cottage in Craryville
4.91 out of 5 average rating, 526 reviews

Columbia County Getaway - Raspberry Ridge Cottage

JenniferRating, 5 stars6 days ago
We had the best time at Raspberry Ridge. So cute, cozy and comfortable. Beautiful grounds. Perfectly stocked kitchen for cooking. Loved having all the animals around. Extra bonus was fresh farm eggs for breakfast in the morning. Hosts were really responsive and wonderful. Didn't want to leave, honestly. A very welcoming respite from a chaotic family week. I couldn't have chosen any better and highly recommend if you are looking for a true rural getaway. Next time I'm in the area visiting family I will definitely plan my trip around availability at this lovely stay.
Top guest favourite
Flat in Northampton
4.95 out of 5 average rating, 241 reviews

Cedar Wet Room w Soaking Tub

AlexRating, 5 stars3 months ago
It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.
Superhost
Cabin in Ghent
4.9 out of 5 average rating, 283 reviews

Guesthouse close to hiking, shopping and ski!

ReedRating, 5 stars1 month ago
We truly had a fantastic stay at Donna's quaint guesthouse in Ghent! The lovely cabin and many available amenities had everything we could have asked for, and more! Donna was extremely welcoming, kind, and communicative, providing us with clear information for the check-in/out process and going the extra mile to offer local recommendations to make us (including our pup) feel at home during our time away. We would certainly go back in a heartbeat!
Guest favourite
Home in Mount Tabor
4.92 out of 5 average rating, 183 reviews

Spring/Summer Fun Treasures Waiting

JustinRating, 5 stars2 months ago
Great place. Was a bit further from Stratton but close to Manchester and Rutland for food options. It is check in with the hosts - clearly in the instructions - which I overlooked upon booking. The place was just as described and the event brought over blueberry muffins which was a nice touch.
Guest favourite
Tiny home in Jamaica
4.94 out of 5 average rating, 1,258 reviews

Apple Blossom Cottage: A Tiny House

ElizabethRating, 5 stars6 days ago
This tiny home is a charm! And, the location - if you are exploring south-central Vermont, as I was - is great. The tiny home has everything you need, and nothing that you don't. I had a perfect stay of two nights here - very enjoyable.
Top guest favourite
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 favourite
Flat in Saratoga Springs
4.91 out of 5 average rating, 269 reviews

Peaceful Getaway - 12 Mins to Saratoga Race Track

MaggieRating, 5 stars2 weeks ago
Dan’s place is wonderful for a quiet, romantic getaway. We loved the deck and the big green space to walk our dog. The apartment was spotless and smelled clean. Dan was very responsive and helpful. My wife and I are hoping to come back someday!

Family-friendly home rentals with a pool

Guest favourite
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

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

NikkiRating, 5 stars2 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 favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 weeks 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 favourite
Home in Ghent
4.88 out of 5 average rating, 314 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

GaryRating, 5 stars1 week ago
Great place. As described. Met our expectations.
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars6 months ago
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Guest favourite
Home in Canaan
4.99 out of 5 average rating, 87 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

RachelRating, 5 stars1 day ago
A group of nine old college friends met at this lovely location for a weekend reunion. The house is exactly how it is described and incredibly clean and charming. The hosts were very communicative and incredibly accommodating. The kitchen was well stocked and had everything we needed to cook and feel right at home. The dining room is a beautiful space to gather and the whole house is comfortable, clean and inviting. We love that everyone had their own room and the bathrooms were incredibly clean with lots of extra products on hand. The bedrooms were streamlined without a lot of clutter and very comfortable beds. Everyone in our group remarked that they had a great night sleep. The house has a very interesting history and although it is an older home the owners did a fabulous job with updates and still kept all the original charm and character. Although the weather didn't fully cooperate, we were able to take a beautiful hike close by. We hope to get the chance to stay again next year
Guest favourite
Apartment in Hancock
4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.
Guest favourite
Flat in Northampton
4.97 out of 5 average rating, 362 reviews

1880s sun-bathed beauty in best downtown location

AliciaRating, 5 stars2 weeks ago
Great Airbnb in Northampton. Lovely decor and thoughtful appointments. Kitchen is well stocked. Beds are comfy. Sue is a terrific host. This is the 2nd time I've stayed in one of her Airbnbs while visiting my daughter who attends a nearby college. Free parking is a major perk as Northampton is a vibrant town with many restaurants and shops. So convenient to walk into town for a morning coffee or stroll home after dinner. Great location and neighborhood. I definitely recommend !
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 217 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars2 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

Destinations to explore