
Pet-friendly holiday rentals in Chittenden
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Top-rated pet-friendly home rentals in Chittenden
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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.

Breadloaf Hut. Glamping, hiking, biking, foliage
Hiker, writers’, gravel/mountain biker's paradise! Our quiet glamping retreat provides easy access to miles of wilderness. The hut has a cozy bed, kitchenette, and camping basics making for an easy and cozy getaway. Follow a trail to the Catamount Trail or drive a few minutes to the Long Trail. Enjoy miles of gravel biking from the door or go to Moosalamoo or Rochester for prime mountain biking trails. In the evening, sit on the deck under a blanket of stars and warm your toes by the fire.

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

Earthen Yurt in Green Mtn Wonderland
Secluded mountain wonderland near Vermont's best hiking, mountain biking, and swimming holes! Enjoy a 25-acre homestead all to yourself, w/two beautifully-appointed yurts & a cabin. One-of-a-kind sculpted earth design, persian rugs, organic linens, & full kitchen w/many artisan touches. Stargaze around the fire circle under a glittering dark sky. A paradise for outdoor adventurers & nature lovers; a haven for digital nomads, writers, & creatives; a refuge of lush natural beauty & deep quiet.

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.

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.

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.

The Guest House at Sky Hollow
This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Dog heavenly! Private, beautiful and relaxing.
Bright, secluded, second floor one room suite with private bathroom overlooking Mill River and across a covered bridge. No neighbors visible, but near town. Fly fish in the back yard, sit around the firepit, enjoy fall foliage, and hike and ski. Swinging bridge and Appalachia long trail very nearby. Close to three ski resorts: Killington, Okemo, and Pico. Dogs are welcome and loved, with plenty of room to run. Comfortable queen-sized bed and couch.

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.

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST
Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

Vermont Hill Top Studio
You can see the stars from your Bed at Night - Studio space with a private entrance located on the quiet eastern end of our house. Twelve foot window provides spectacular views of Bird Mountain, & Killington, Pico Castleton is located in a great central location which acts as a great launching point for Lake Bomoseen , Killington / Pico Resort , or exploring the state
Popular amenities for Chittenden pet-friendly home rentals
Pet-friendly house rentals

Killington area home - 4-seasons & hot tub

Modern Retreat next to Mountain Top Inn,Killington

Green Mountain Getaway

The McKinley House

Vermont Highland

Rand’s Retreat

Convenient Vermont Getaway

Modern Comfort Meets Country Charm | 3BR Estate
Pet-friendly home rentals with a pool

Epic Views of the Green Mountains

NEW Killington Studio: Great Location! Comfy. 431

SugarBear- Pool, Hot Tub, 2 En Suites BR

Moon Valley Country Retreat no clean fee pets yes

Dog-Friendly/Spa Onsite/Pool/Wine Bar

Charming Killington get away with pool, sleeps 4

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

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Private, pet-friendly home rentals

Easy access to downtown Rutland

Cute fully furnished studio apt

Scenic Vermont Green Mountain Retreat

House on Molly Brook Trail

Cozy cottage near Killington & Sugarbush

Historic Farmhouse in Middlebury

Firefly Cottage

Rustic and Cozy Vermont Getaway at Sugarwood Cabin
When is the best time to visit Chittenden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹42,696 | ₹44,549 | ₹36,257 | ₹26,377 | ₹25,847 | ₹26,377 | ₹21,436 | ₹23,995 | ₹21,172 | ₹23,024 | ₹19,319 | ₹39,609 |
| 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 pet-friendly in Chittenden

Total holiday rentals
Explore 20 holiday rentals in Chittenden

Nightly prices starting at
Chittenden holiday rentals start at ₹9,704 per night before taxes and fees

Verified guest reviews
Over 1,030 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 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!
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- Pet-friendly rentals Rutland County
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- Pet-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Bolton Valley Resort
- West Mountain Ski Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Lake George Expedition Park
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Montshire Museum of Science
- Fox Run Golf Club
- Country Club of Vermont