
Pet-friendly holiday rentals in Rutland
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Top-rated pet-friendly home rentals in Rutland
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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

Adorable one bedroom studio in 1844 farmhouse.
Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

Cozy Bow House Perched in Trees w/ Hot Tub & View
The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Beautiful Woodstock Home-Perfect for entertaining
Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

The Oaks - secluded rural estate w/ amazing views
Relax in this private house secluded off a 1,000-ft driveway in the hills of NH overlooking Mt. Ascutney and the Connecticut River valley. This is the 45-acre estate known as "The Oaks" previously owned by painter Maxfield Parrish. Huge oak trees and rocky ledges abound. Great for gatherings with family or friends. Close to Dartmouth College, Woodstock, and ski areas - or just sit on the porch and take in the views. Weddings and reunions can be hosted (tent rentals and catering by others).

1958 Classic "Hunting Cabin" w/ Breathtaking Views
Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

Sunset Cabin - your private romantic hideaway
Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

Private Modern Cabin w/View of Fields, Hills
Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

Stylish Vermont Cabin | Views · Trails · Luxe
Spring and summer at the Red House. A place to slow down, get away from it all, and take the views in! Watch the hills come back to life from the porch, coffee in hand, as green rolls up the valley and wildflowers take over fields. Hike or bike to a trailhead five minutes from the front door. Gather around the fire pit and wonder how dark and wide the night sky can be. The Red House sits within reach of some of the best restaurants in Vermont and awaits the discerning traveler.

Cabin on the Hill
Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Yurt In The Woods - Come to the Yurt.
The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Private Barn On a Hilltop in Fairlee, Vermont
This carefully renovated barn is located in the hills of Fairlee, five minutes from I-91. A stand-alone private space with two spacious living areas and decks overlooking ponds and the mountains. You're welcome to bring your dog; please note there is a $75 pet fee for the length of your stay. With direct access to extensive hiking trails and minutes from Lake Morey and the Lake Morey Country Club there's lots of fun things to do.
Popular amenities for Rutland pet-friendly home rentals
Pet-friendly house rentals

Epic Views of the Green Mountains

Mountain Getaway Pet friendly

Modern Farmhouse on 25 Acres - Superb Views

Berry Mountain Lodge: Mountain Views by Lake & Ski

Comfortable farmhouse with stunning views

Private & Cozy Farmhouse in New Hampshire

The Guest House at Sky Hollow

Convenient Vermont Getaway
Pet-friendly home rentals with a pool

Spring Deals • Quiet Dog-Friendly Mountain Escape

Ranch at Mendon Mt Orchards

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

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

Topridge 3BR w Incredible View & Private Hot Tub!

Beautiful Bromley/Manchester VT Retreat w/hot tub
Private, pet-friendly home rentals

Nature cabin | fire pit, fireplace, yard + privacy

Quaint stone house!

The Beaver Pond Treehouse @ Vermont ReTREEt

Fat Sheep Farm & Cabins - Sunrise Cabin

Sunday Mountain Surprise

Hancock hideaway

Quiet Vermont Farmhouse

Apple Blossom Cottage: A Tiny House
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $271 SGD | $315 SGD | $287 SGD | $233 SGD | $270 SGD | $293 SGD | $373 SGD | $364 SGD | $331 SGD | $414 SGD | $287 SGD | $357 SGD |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°C | -2°C |
Quick stats about holiday rentals that are pet-friendly in Rutland

Total holiday rentals
Explore 40 holiday rentals in Rutland

Nightly prices starting at
Rutland holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 4,100 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
40 of Rutland holiday rentals include wifi access

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

4.9 Average rating
Rutland stays are highly rated by guests – averaging 4.9 out of 5!
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- Pet-friendly rentals Windsor County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Squam Lake
- Killington Resort
- Weirs Beach
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dartmouth College
- Ice Castles
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Warren Falls
- Squam Lakes Natural Science Center




