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House holiday rentals in Chittenden

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Quick stats about house rentals in Chittenden

  • Total holiday rentals

    Explore 60 holiday rentals in Chittenden

  • Nightly prices starting at

    Chittenden holiday rentals start at £127 per night before taxes and fees

  • Verified guest reviews

    Over 1,990 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Chittenden holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chittenden rentals

  • 4.9 Average rating

    Chittenden stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated house rentals in Chittenden

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

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Top guest favourite
A sunroom showcases high wooden ceilings with skylights, enhancing natural light. A comfortable seating area, set with a light-colored couch and side table, is positioned next to large windows offering views of the outdoors. A dining table, accompanied by four chairs, occupies one corner of the space.
Home in Rutland

Mountain Getaway Pet friendly

Escape to our charming getaway, ideally located in Rutland just 20 minutes from the world-famous Killington Ski Resort! Whether you're here for skiing, snowboarding, hiking, or simply enjoying the serene beauty of Vermont, our home offers the perfect base for all your adventures. Our home offers a cozy and welcoming environment, perfect for families, couples, and groups of friends. You'll love the combination of comfort, convenience, and proximity to the best of Killington's outdoor adventures.

4.94 out of 5 average rating, 126 reviews
Top guest favourite
Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

4.99 out of 5 average rating, 170 reviews
Top guest favourite
A new hot tub with jets is positioned under a wooden structure, surrounded by grass and landscaped areas. A tranquil view of distant mountains and trees is visible in the background, creating a peaceful outdoor setting.
Home in Rutland

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mnt views, peaceful brook on 1+ acre. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV/nintendo switch.

4.9 out of 5 average rating, 248 reviews
Guest favourite
The exterior of a two-story white house is pictured, featuring a red front door and black shutters on the windows. A well-maintained lawn with green grass and a tree is visible in the front yard, presenting a welcoming appearance.
Home in Rutland

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.

4.82 out of 5 average rating, 404 reviews
Top guest favourite
Home in Rutland

Kingsley Homestead - walking distance to Downtown

Come stay in our quiet and relaxing two bedroom suite. We accommodate 4 people comfortably. We are very close to Rutland Golf ⛳️ , Pine Hill Park, Killington. Walking distance from downtown. There is a queen bedroom with a equipped kitchenette, large living room, and bath with shower and a whirlpool tub to relax in after a long day of outdoor adventures. There is a second bedroom that has two twin beds. Many small appliances. No stove. There is a two-burner portable stove.

4.98 out of 5 average rating, 163 reviews
Top guest favourite
Home in Mendon

New Firepit, Great Location, Dog Friendly, Kitchen

Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

4.98 out of 5 average rating, 175 reviews
Top guest favourite
The exterior of a renovated one-room schoolhouse is presented, set amidst lush green foliage. A vibrant red door stands out against the white walls, while a well-maintained hedge borders the property. Surrounding trees provide a serene backdrop, creating a peaceful atmosphere.
Home in Rutland

One Room School House. No Cleaning Fees!

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

5.0 out of 5 average rating, 163 reviews
Guest favourite
Home in Pittsfield

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

4.85 out of 5 average rating, 256 reviews
Superhost
Home in Rutland

Rustic Vermont cottage for families - self checkin

Enjoy the warmth & comfort of this spacious 3-bedroom home featuring original hardwood floors and beautiful wood accents. Bring the whole family or close friends to this clean, well-furnished home that serves as a convenient home base for outdoor adventure-seekers. 20-min to Killington, 15-min to Pico. A few minutes drive to Rutland's best eateries and shops. First time in Rutland? Read the neighborhood description!

4.78 out of 5 average rating, 113 reviews
Top guest favourite
A cozy living room area is presented with a dark gray sofa adorned with white pillows. A television is positioned on a light-colored console, with framed black-and-white nature photographs displayed on the wall. Natural light filters through the windows, enhancing the serene environment.
Home in Pittsford

Convenient Vermont Getaway

Conveniently located near the top ski and mountain bike attractions, incredible trails, resorts, and the towns of Woodstock, Middlebury, Killington, Pico, and Rutland. This historic property has been in existence since 1832 and has been lovingly maintained with a backdrop of the Adirondacks beyond the picturesque pasture. This one bedroom apartment is located downstairs in the two story duplex.

4.92 out of 5 average rating, 131 reviews
Guest favourite
A snow-covered pathway leads to a charming white house surrounded by trees blanketed in snow. The structure features a gabled roof and a small cupola, with snow drifts framing the entrance. The clear blue sky provides a bright contrast against the winter scene.
Home in Pittsford

Colburn's Carriage House

Only 30 minutes from Killington/Pico ski resorts, and 20 minutes from Mountain Top Inn and Chittenden Reservoir, Colburn's Carriage House is a charming and convenient getaway. 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.

4.93 out of 5 average rating, 222 reviews
Top guest favourite
A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.
Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Embracing the dramatic beauty of Rochester's north hollow the house is a serene retreat where connection to your partner, family and the environment will thrive. Unplug, recharge, renew and enjoy all that mountain living has to offer.

4.97 out of 5 average rating, 157 reviews

Popular amenities for house rentals in Chittenden

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Superhost
Home in Killington

Luxury Condo Tucked in the Heart of Killington

4.86 out of 5 average rating, 260 reviews
Guest favourite
A refreshing pool is visible in the foreground, featuring a blue inflatable shark and a colorful inner tube. A shaded seating area with a large blue umbrella is highlighted by striped chairs. In the background, a charming building peeks through lush green foliage.
Home in Killington

CountryBear- AC, Pool, Hot Tub, Fire Pit, Grill

4.9 out of 5 average rating, 134 reviews
Guest favourite
Home in Killington

Golf and Mountain Biking outside the door!

4.89 out of 5 average rating, 141 reviews
Guest favourite
The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.
Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

4.92 out of 5 average rating, 114 reviews
Guest favourite
Home in Killington

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

4.92 out of 5 average rating, 172 reviews
Guest favourite
The outdoor area features a serene in-ground pool surrounded by a concrete deck. Comfortable seating is provided by four woven chairs and matching side tables. Lush greenery and well-maintained landscaping frame the area, enhancing the peaceful atmosphere.
Home in Rutland

4 bedroom home w/mountain views & outdoor pool

4.79 out of 5 average rating, 47 reviews
Top guest favourite
The living area features a floor-to-ceiling stone fireplace framed by elegant wooden beams. Comfortable seating is arranged around a rustic coffee table atop a patterned rug, creating an inviting space for relaxation and socializing.
Home in Killington

Topridge | Luxe 4BR w Game Room & Foliage Views!

4.97 out of 5 average rating, 37 reviews
Guest favourite
The exterior of a newly renovated retreat showcases a wooden structure surrounded by trees. A fire pit is set with several dark chairs arranged in a circular formation. Soft light emanates from the large windows, providing a glimpse into the warm interior spaces.
Home in Bridgewater

Luxurious family retreat home in the mountains

4.92 out of 5 average rating, 61 reviews

Weekly house rentals

Top guest favourite
Home in Rochester

Bill’s Barn Rochester Vermont 3 Bdrm entire house

4.97 out of 5 average rating, 112 reviews
Top guest favourite
A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.
Home in Rochester

The Guest House at Sky Hollow

4.97 out of 5 average rating, 240 reviews
Top guest favourite
A serene view captures a green field leading to distant mountains, with a weathered barn nestled among trees. A small shrub occupies the foreground, providing a sense of depth. The landscape reflects a tranquil countryside setting.
Home in Bethel

Vermont private retreat with gorgeous views.

4.96 out of 5 average rating, 169 reviews
Top guest favourite
A comfortable living area features a light-colored sofa and two blue chairs arranged around a wooden coffee table. Natural light enters through multiple windows, and wall art adds a touch of charm. A ceiling fan is positioned above, enhancing the relaxed ambiance.
Home in Chittenden

Cozy two bedroom cottage in Vermont

4.98 out of 5 average rating, 81 reviews
Guest favourite
Home in Chittenden

Cozy, comfortable home in N Chittenden Vt

5.0 out of 5 average rating, 10 reviews
Guest favourite
An open living area features warm wood paneling and a spacious bar area with two high stools. A dartboard is mounted on the wall adjacent to a window, while large windows allow natural light to brighten the space. Comfortable seating arrangements are visible in the background.
Home in Chittenden

Maple Mountain Lodge - 3 bedroom home

5.0 out of 5 average rating, 42 reviews
Guest favourite
The exterior of a yellow cottage is showcased against a backdrop of colorful autumn foliage and rolling mountains. A manicured lawn leads to a fenced area, providing a peaceful setting for outdoor activities enhanced by the natural beauty surrounding the property.
Home in Chittenden

MT Top Inn-6 Minute Walk-4+ BR-Pets OK & Grill-Ski

4.88 out of 5 average rating, 34 reviews
Guest favourite
A spacious living area features a cathedral ceiling adorned with wooden beams. Large floor-to-ceiling windows allow for abundant natural light and views of the surrounding forest. Comfortable seating arrangements include a dark sofa and matching armchairs, complemented by a wooden coffee table and decorative plants.
Home in Chittenden

Private Vermont Retreat | Mt Top Inn & Killington

4.95 out of 5 average rating, 64 reviews

Private house rentals

Guest favourite
Home in Killington

Cedar Wood Lodge

5.0 out of 5 average rating, 17 reviews
Guest favourite
A gray two-story house is framed by lush green grass and colorful foliage. A wraparound porch features white railings and steps leading to the yard. Two balconies extend from the upper level, complementing the inviting exterior under a clear blue sky.
Home in Rutland

Summer Lodge Near Killington w/ Pool Table

4.91 out of 5 average rating, 78 reviews
Top guest favourite
Home in Rutland

4BR Home | Walk Downtown Rutland + Trails

4.98 out of 5 average rating, 54 reviews
Guest favourite
Home in Rutland

The Green Mountain Retreat

4.94 out of 5 average rating, 16 reviews
Top guest favourite
A spacious living area features a large leather sectional sofa facing a glass coffee table. Natural light floods in through multiple large windows, framed by dark trim. A cozy reading nook is seen in the corner, adorned with a decorative throw and a small side table.
Home in Pittsfield

Skyeburst | Modern Mtn Home

4.98 out of 5 average rating, 46 reviews
Superhost
A hot tub is positioned on a gravel patio, overlooking a serene landscape of trees and mountains. Outdoor seating is available nearby, complementing the tranquil setting. The clear blue water of the hot tub reflects the sky, inviting relaxation in a peaceful environment.
Home in Mendon

Lakeview home

4.85 out of 5 average rating, 65 reviews
Top guest favourite
A two-story gray house with an A-frame design is surrounded by trees. Large windows fill the front facade, allowing natural light inside. A spacious wooden deck features multiple seating areas and an umbrella, promoting outdoor relaxation.
Home in Mendon

The Old Home Place!

5.0 out of 5 average rating, 53 reviews
Guest favourite
A bright kitchen is showcased with modern appliances and ample counter space. The wooden island center features a red bowl. A dining area with a small table is visible in the background, accented by natural light from a nearby window.
Home in Rutland

Cheerful home near Killington, Okemo, Pico, trails

4.93 out of 5 average rating, 96 reviews

When is the best time to visit Chittenden?

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Avg. price£334£360£286£246£263£247£259£254£244£256£247£325
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