Family-friendly vacation rentals in Rutland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Rutland family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Plymouth
4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

MichaelRating, 5 stars1 month ago
Nice place thanks Mike
Guest favourite
Chalet in Killington
4.84 out of 5 average rating, 250 reviews

Killington Chalet - Hot Tub, Sauna, Boot Dryer

MauraRating, 5 stars1 month ago
Nice space for a group, plenty of room for dining and relaxing. Clint was very responsive and gave excellent instructions. Appreciated the hospitality!
Guest favourite
Chalet in Stockbridge
4.92 out of 5 average rating, 181 reviews

Killington ski house winter MTbike -new jacuzzi

ZachRating, 5 stars2 months ago
Great place to stay! The hot tub after a long day of snowboarding was amazing. Dean responds fast to any questions you have too. Definitely recommend
Guest favourite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars1 month 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 favourite
Condo in Killington
4.97 out of 5 average rating, 144 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

MichaelRating, 5 stars1 month ago
Great spot near the mountain. nice community pool and hot tub.
Top guest favourite
Home in Ludlow
4.97 out of 5 average rating, 158 reviews

Ski Chalet with Hot Tub on Okemo Mountain

MichaelRating, 5 stars1 month ago
Great house, location, and host! Eric was very helpful, communited timely, and is super organized. The house is in a great private location right near Okemo, plenty of restaurants, and a grocery store. The house felt bigger than the square footage states and was perfect for our two families (4 adults and 4 kids aged 9-12). We are usually disappointed in how clean rentals are upon our arrival, but this house was basically impeccable which especially isn't easy in the mountains! The upstairs is perfect for a kids room and the living space was nice and cozy, but didn't feel small. Plenty of room for everyone. I highly recommend this house, the hosts, and Okemo. It was our first time on this mountain and really enjoyed the family friendly atmosphere and terrain while also having plenty of advanced trails as well. Overall we had an A+ weekend.
Top guest favourite
Cabin in Ripton
5 out of 5 average rating, 106 reviews

#7 - Hemlock Hideaway Cabin

ChrisRating, 5 stars2 months ago
Home now after a couple days at the cabin. Feeling fully rested and can’t express enough how much we needed this getaway. Ago and Marty go above and beyond to make you feel comfortable and provide you with everything you could need to relax and have a great time. We will be coming back here. Hopefully soon.
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

Guest favourite
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 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 favourite
Home in Bristol
4.88 out of 5 average rating, 155 reviews

Large New England Home w/ Gorgeous Mountain Views

ChristopherRating, 5 stars2 months ago
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.
Guest favourite
Home in Waitsfield
4.96 out of 5 average rating, 163 reviews

Mid century modern gem with views of Sugarbush

PhilippeRating, 5 stars2 months ago
Place was as advertised. Beautiful, great location, great views, close to convenient grocery shopping and slopes. We'd love to come back some day.
Guest favourite
Cabin in Danby
4.89 out of 5 average rating, 296 reviews

April/May special So Vt Cabin Mt Tabor Treasure

MelissaRating, 5 stars1 month ago
A great escape. We enjoy our stays here. We are booked again in June. Lori is so attentive. She is always one step ahead. Thank you! 😀
Guest favourite
Home in Rochester
4.95 out of 5 average rating, 196 reviews

The McKinley House

GarethRating, 5 stars2 months ago
We had a great stay, lovely welcoming home and great location - short walking distance to nice places in town and 30min drive to either Sugarbush or Killington/Pico. Thank you!
Guest favourite
Apartment 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!
Top guest favourite
Home in Ballston Spa
4.94 out of 5 average rating, 109 reviews

Time to Relax, close to Saratoga.

SiddharthRating, 5 stars8 months ago
The house was beautiful and Rhonda was great, she was very responsive and helpful. We felt right at home and enjoyed the place more than Lake George :) , the hot tub and pool were great and i would recommend anyone coming to this area to definitely book the place if they get the chance.
Top guest favourite
Chalet in Wells
4.9 out of 5 average rating, 143 reviews

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

TomRating, 5 stars2 months ago
Rita’s chalet is really clean and the view around it is amazon. The place is well stocked with games for fun and firewoods for warmth. Upon request, Rita was able to accommodate our late checkout request with a reasonable surcharge. We have enjoyed our stay at Rita’s place and would definitely come back next time when we are around

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.
Top guest favourite
Apartment in Barre
4.94 out of 5 average rating, 163 reviews

Relax in Recreation Paradise!

JenniferRating, 5 stars2 months ago
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!
Guest favourite
Guest suite in Killington
4.95 out of 5 average rating, 145 reviews

Cozy, spacious, 3 bedrooms, 4 beds, 5 mi to K Rd.

JoshRating, 5 stars1 month 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 favourite
Condo 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.
Top guest favourite
Condo in Warren
4.97 out of 5 average rating, 128 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

PedroRating, 5 stars2 months ago
Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy
Guest favourite
Guesthouse in Granville
4.9 out of 5 average rating, 896 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars1 week ago
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.
Superhost
Condo in Killington
4.8 out of 5 average rating, 107 reviews

*Killington Summer Rental: 3 Bdrm, 2 Bth*

MikeRating, 5 stars2 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
Condo in Killington
4.82 out of 5 average rating, 257 reviews

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

ZacharyRating, 5 stars2 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.

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

  • Total rentals

    80 properties

  • Nightly prices starting at

    $69 CAD before taxes and fees

  • Total number of reviews

    4.1K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    80 properties include access to wifi

Destinations to explore