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Holiday houses in Castleton

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Top-rated holiday rentals in Castleton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 251 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Guest favourite
Home in Fair Haven
4.92 out of 5 average rating, 197 reviews

Historic 4 Bed 2 Bath Victorian Estate Fast Wifi

Ski season has begun! Take it easy at this unique and historic property. Picturesque Victorian Estate next to the Castleton River perfect for weddings and events. You can wake up with birds chirping and fall asleep to the frogs croaking. Church bells ring throughout the day while relaxing on the covered porch. Walk the historic slate sidewalk to the park and downtown for shopping and dining. Minutes to many lakes and trails. Day trips to Killington, Woodstock, Lake George, Vergennes, & Rutland.

Top Guest favourite
An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.
Guest suite in Lake Bomoseen
4.97 out of 5 average rating, 252 reviews

My house is your house!

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.

Top Guest favourite
A vintage gas station building features a white exterior with red lettering spelling 'TEXACO.' Large glass windows line the front, showcasing a clear view of the interior. The American flag is displayed prominently, and a tree-lined background adds a touch of greenery.
Home in Castleton
4.94 out of 5 average rating, 156 reviews

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

Top Guest favourite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 171 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Top Guest favourite
A charming one-bedroom cabin is nestled among tall trees in a forested area. The wooden exterior is complemented by a porch with a railing and flower pots, creating a rustic appeal. Natural light filters through the windows, enhancing the cabin's tranquil setting.
Tiny home in Castleton
4.99 out of 5 average rating, 120 reviews

Cabin-by-the-falls

One-bedroom cabin (one double bed only) for those who want tranquility. Parking at main house and then short walk downhill, then 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.

Top Guest favourite
Barn in Woodstock
4.99 out of 5 average rating, 305 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Top Guest favourite
The cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. A stone walkway leads to the entrance, while a covered wood storage area is visible nearby. Bright green leaves provide a natural canopy, creating a serene atmosphere.
Cottage in Whitehall
4.99 out of 5 average rating, 236 reviews

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Superhost
A living area is presented with a comfortable gray sofa adorned with patterned cushions. Two windows with light-blocking curtains allow natural light to illuminate the room. A coffee table displays magazines and a candle, while a nearby side table holds additional decor.
Apartment in Fair Haven
4.86 out of 5 average rating, 195 reviews

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.

Top Guest favourite
A spacious living area is highlighted by tall windows, allowing ample natural light. Exposed wood beams adorn the ceiling. A comfortable sofa sits across from a coffee table, with a decorative rug beneath. A dining table and chairs are visible, complemented by a bright kitchen area in the background.
Home in Tinmouth
5 out of 5 average rating, 100 reviews

Charming Vermont Schoolhouse

Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Guest favourite
A serene view of a lake framed by abundant greenery, showcasing towering trees and gentle hills in the background. Various charming cabins line the shore, with blue water reflecting the clear sky above.
Cottage in Castleton
4.87 out of 5 average rating, 139 reviews

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

Top Guest favourite
A view of the lakefront area is presented, showcasing a stone patio with four Adirondack chairs arranged in a line. The calm water reflects surrounding trees, while kayaks are visible on the shore, and two individuals enjoy the lake nearby. Steps lead down to the water from the patio.
Home in Poultney
4.94 out of 5 average rating, 163 reviews

Waterfront Cabin • Dock • Fire Pit • Kayaks & SUPs

Relax at this private Vermont lakefront getaway on North Bay. Unwind in a bright, comfortable space with a full kitchen, fast WiFi, and cozy bedrooms. Walk a few steps to the water front to enjoy morning coffee on the dock. Perfect for year-round escapes: -Summer (kayaks, SUPs, floating mat) -Fall (foliage, fire pit, hiking trails) -Winter (skiing, snowshoeing, ice fishing) -Spring (deck, hammock, fishing opener).

Popular amenities for Castleton holiday rentals

When is the best time to visit Castleton?

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Avg. price$273 AUD$285 AUD$271 AUD$271 AUD$306 AUD$306 AUD$309 AUD$306 AUD$292 AUD$341 AUD$280 AUD$298 AUD
Avg. temp-7°C-6°C0°C7°C14°C18°C21°C20°C15°C9°C3°C-3°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Castleton?

    Castleton has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Castleton?

    Experience the best of Castleton with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Castleton?

    Four-legged friends are welcome in Castleton. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Castleton?

    Yes! Work meets play with ease at over 30 vacation rentals in Castleton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Castleton have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Castleton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Castleton have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Castleton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Castleton have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Castleton. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Castleton have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Castleton. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Castleton

  • Total holiday rentals

    Explore 70 holiday rentals in Castleton

  • Nightly prices starting at

    Castleton holiday rentals start at $111 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Castleton holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castleton rentals

  • 4.9 Average rating

    Castleton stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Castleton