Family-friendly vacation rentals in Castleton

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Top-rated family-friendly rentals in Castleton

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov 5 – 12

ﺩ.ﺇ384 per night

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 208 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Feb 1 – 8

ﺩ.ﺇ590 per night

Guest favorite

Home in Rutland

4.81 out of 5 average rating, 291 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

May 27 – Jun 3

ﺩ.ﺇ479 per night

Guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 433 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

America's only original Grist Mill & Covered Bridge residence, as seen on HGTV's "You Live in What?", (Se.2. ep.1) & worldwide on the Netflix travel series "World's Most Amazing Vacation Rentals" (Se. 2, ep 7). Join us for our 10th season as central Vermont's iconic adult getaway featuring private beach on Vermont's warmest river with tethered, relaxing, float tubes & two private decks overlooking Mill River's secluded waterfall. Come make history with us ! Near Killington & Okemo Mtns.

Nov 27 – Dec 4

ﺩ.ﺇ1,280 per night

Guest favorite

Home in Poultney

4.93 out of 5 average rating, 276 reviews

Waterfront lakehouse with incredible views!

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Sep 19 – 26

ﺩ.ﺇ1,431 per night

Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 786 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Dec 6 – 13

ﺩ.ﺇ397 per night

Guest favorite

Home in Leicester

4.98 out of 5 average rating, 135 reviews

Luxurious Cottage Massage Therapy Studio On Site

Meticulously clean, private getaway, custom built home to yourself. Beam ceilings, wood floors, oriental carpets, Alexa, grand piano & lots of art. Complete kitchen, pancake mix & Vt maple syrup. Coffee, teas, orange juice, bagels, cream cheese, granola & fruit. Shower bath with shampoo, conditioners, body wash etc. New private deck, tables & chairs... outside art work. Massage available in log cabin on site $70 Ninja Warrior outside gym with trampoline & slack line

Nov 5 – 12

ﺩ.ﺇ642 per night

Guest favorite

Cabin in Hancock

4.95 out of 5 average rating, 221 reviews

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

May 7 – 14

ﺩ.ﺇ549 per night

Guest favorite

Cabin in Hancock

4.97 out of 5 average rating, 343 reviews

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

Apr 23 – 30

ﺩ.ﺇ621 per night

Guest favorite

Cabin in Fair Haven

4.95 out of 5 average rating, 158 reviews

Glamping (Glamorous Camping) in Glen Lake Woods

"Glamping" is a combination of camping and comforts. Outdoor toilet and outdoor shower. We provide plenty of clean drinkable water for cooking and showers. The cabin has an outdoor portable restroom that is serviced weekly, outdoor shower, cathedral ceilings, open floor plan, full kitchen, ceiling fans, carpeted sleeping loft with linens, Wifi . We are sorry we do not allow pets as stated in house rules.

Aug 30 – Sep 6

ﺩ.ﺇ423 per night

Guest favorite

Apartment in Rutland

4.96 out of 5 average rating, 523 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

Apr 2 – 9

ﺩ.ﺇ371 per night

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 30 – Oct 7

ﺩ.ﺇ420 per night