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Vacation rentals in Chittenden

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Top-rated vacation rentals in Chittenden

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

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Home in Rutland

5 out of 5 average rating, 130 reviews

ONE ROOM SCHOOL HOUSE

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. It is now a separate, private, room. New European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace/stove for heat and atmosphere. Storage for clothing, skis, snowboards. Exterior bicycle rack. Circular driveway for off-street parking. High speed internet and 65 inch Roku TV with surround sound. Everything brand new. We have added three season screened porch.

Tiny home in Pittsford

4.96 out of 5 average rating, 167 reviews

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.

Farm stay in Salisbury

4.96 out of 5 average rating, 321 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This adorable 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.

Rental unit in Chittenden

5 out of 5 average rating, 239 reviews

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont. * We are following the guidelines set up by the W.H. O. and we are leaving a window between reservations to disinfect our suite due to Covid-19.

Cabin in Hancock

4.95 out of 5 average rating, 238 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.

Cabin in Chittenden

4.96 out of 5 average rating, 110 reviews

Cabin on The Hill

Relax with the whole family at this peaceful place. Private, cozy, clean, comfortable getaway in Chittenden Vermont. This beautiful cabin is off the grid with solar power and push button generator. Chittenden is a small drive to endless recreational activities for every season. It is the perfect rustic space for a couple or a small family. It is centrally located between Killington and Rutland. Everything you need is within a 20 to 30 minute drive.

Cabin in Rochester

4.95 out of 5 average rating, 437 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Rental unit in Rutland

4.89 out of 5 average rating, 138 reviews

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

Cabin in Hancock

4.97 out of 5 average rating, 358 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.

Rental unit in Rutland

4.96 out of 5 average rating, 570 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.

Condo in Killington

4.94 out of 5 average rating, 161 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Updated Ski on/off at the base of Pico overlooking the mountain! FREE Shuttle to Killington right downstairs. Roll out of bed, walk to the lift and finally get first tracks! Or, let yourself relax and just watch those getting first tracks from the comfort of the private balcony overlooking the trails!

Rental unit in Chittenden

4.95 out of 5 average rating, 258 reviews

Cozy Apt Close to Mountain Top Inn & Ski Areas

Cute apartment just two miles from Mountain Top Inn & Resort and 20-25 minutes to Killington & Pico Resorts. Chittenden Reservoir is 2 miles away. Close to golf,mountain biking, hiking, kayaking, horseback riding. Great apartment on wooded lot close to amenities with private deck.

Vacation rentals for every style

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Popular amenities for Chittenden vacation rentals

Free parking on premises

Air conditioning

Stay near Chittenden's top sights

Pico Mountain Ski Resort100 locals recommend

Deer Leap Trail40 locals recommend

Green Mountain National Golf Course35 locals recommend

Mountain Top Inn & Resort32 locals recommend

Clear River Tavern23 locals recommend

Gifford Woods State Park20 locals recommend

Other great vacation rentals in Chittenden

Guest suite in South Chittenden

5 out of 5 average rating, 19 reviews

Roomy 2-floor apt near Killington/Mt. Top

Rental unit in Goshen

4.93 out of 5 average rating, 43 reviews

Rocky Meadow Farm

Chalet in Mendon

5 out of 5 average rating, 22 reviews

Unique Luxury-Minutes to Skiing-Hidden Speakeasy

Home in Chittenden

4.86 out of 5 average rating, 14 reviews

Backyard Deck+Modern Interior | House on the Rocks

Home in Chittenden

5 out of 5 average rating, 48 reviews

Gigi and Pops' Secret Cabin

Home in Chittenden

4.93 out of 5 average rating, 14 reviews

VT Getaway/Mtn Top Inn/Killington/Pico/VAST Trails

Tiny home in Rutland

4.98 out of 5 average rating, 40 reviews

Curious Little Cottage

Home in Pittsford

5 out of 5 average rating, 27 reviews

Green Mountain Getaway

Quick stats about vacation rentals in Chittenden

Total rentals
90 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Chittenden?
Four-legged friends are welcome in Chittenden. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Chittenden have free parking?
Absolutely! We offer over 40 house rentals with free parking in Chittenden. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Chittenden?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Chittenden vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chittenden, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Chittenden have wifi?
Absolutely! We offer over 40 house rentals with wifi in Chittenden. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chittenden have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Chittenden. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Chittenden?
Chittenden has more than 70 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 Chittenden?
Experience the best of Chittenden with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chittenden have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Chittenden. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Chittenden?
Yes! Work meets play with ease at over 50 vacation rentals in Chittenden featuring dedicated workspaces. Stay connected and productive in your home away from home.

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