
Family-friendly holiday 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.

Cabin-by-the-falls
One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Mi Casa es su Casa!
Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

The Cottage in East Poultney
The Cottage is located in historic East Poultney next to the old Poultney schoolhouse (now historical society). Just over 1 mile to the town of Poultney. The sidewalk starts (or ends how you look at it) in front of the cottage which leads to town. Great for a walk or bike ride. Pico, Killington and Bromley Mountains all less than an hour drive. Plentiful fishing and boating opportunities. 3 miles to Lake St Catherine, under 10 miles to Lake Bomoseen. Slate Valley bike trails surround the area.

Cozy Contemporary Downtown Texaco
Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Charming tiny house with great VT location!
Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

Moon Valley Country Retreat no clean fee pets yes
Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim 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 a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Quaint 1-bedroom cottage on Blue Ledge Farm
This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Apartment in Vermont Historic Home
This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Cozy Home in Poultney, Vermont.
If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

Spacious One Bedroom - Walk To Town, Restaurants
Enjoy this cute and newly renovated one bedroom apartment that is within walking distance to the Fair Haven town center. Step outside listen to the church bells ring. Comfortable queen size bed with mattress topper, new memory foam sofa bed in the living room with an electric fireplace, retro arcade game console, smart television, DVD player, fully applianced kitchen, and a bathroom with a stand up shower. Plenty of off street parking. Large back yard with fire ring.

Killington Retreat | Deck-Fire Pit-Mountain Views!
Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Family or couples retreat on Lake Bomoseen
Newly Renovated! 3 bedrooms 2 baths relax and take in the lake views on the multiple decks. Great for a small family or couples retreat. Boat slip and dock and 100 feet of frontage to enjoy. Bring your boat or kayak or rental. Fully stocked kitchen. Just Bring your SHEETS and TOWELS. Sunsets are great! Lake activities or hiking, biking, horseback riding, all close by. Close to Rutland and Skiing! No large parties or events
Popular amenities for Castleton family-friendly rentals
Family-friendly home rentals with a hot tub

Ski Back to Trail Creek!

The Owl’s Nest in Landgrove

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

SugarBear- Pool, Hot Tub, 2 En Suites BR

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Beautiful Spacious Condo at Killington Resort

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

Newly renovated ski retreat at Killington
Family- and pet-friendly home rentals

Picturesque Cabin on the Mettowee

The Smithy Cottage at Consider Bardwell Farm

Contemporary Queen

Glamping Cabin with Private Pond and Mountain View

Hancock hideaway

Sculpted Earthen Yurt Near World Class Skiing

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC

The Guest House at Sky Hollow
Family-friendly home rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Ranch at Mendon Mt Orchards

1 BR Best Location w/ Pools/Massage Chair/Hottub!

Winterplace - Steps away from Slopes

One Bedroom Suite Near Okemo

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

Pow On Pico Great time 1 nte Ok 1 bedrm Ski in out
When is the best time to visit Castleton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £266 | £252 | £266 | £222 | £287 | £314 | £252 | £240 | £266 | £266 | £266 | £277 |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are family-friendly in Castleton

Total holiday rentals
Explore 50 holiday rentals in Castleton

Nightly prices starting at
Castleton holiday rentals start at £74 per night before taxes and fees

Verified guest reviews
Over 1,320 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Castleton holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castleton rentals

4.8 Average rating
Castleton stays are highly rated by guests – averaging 4.8 out of 5!
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- Family-friendly rentals Rutland County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Saratoga Race Course
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Fort Ticonderoga
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- National Museum of Racing and Hall of Fame
- Montshire Museum of Science
- Adirondack Extreme Adventure Course
- Dartmouth College
- Congress Park
- Middlebury College
- Trout Lake




