Family-friendly vacation rentals in Rutland

The exterior of a two-story yellow house is visible, featuring a welcoming entrance with a decorative door. Symmetrical windows are arranged on the facade, flanked by neatly trimmed shrubs. A concrete pathway leads from the street to the entrance, surrounded by a manicured lawn.

4.88 out of 5 average rating, 286 reviews

Home Sweet Grove Street

Enormous 4 bedroom/1 bathroom apartment. 2000 sq ft.. Second floor. Entrance in front of the house. Parking in rear. Large dining room, living room and kitchen. Covered porch off of kitchen to enjoy some time outside. Tons of natural light. Perfect for large families or groups of friends. Dining room table seats 10+. House is one block from downtown. Walk to the restaurants, bars, movie theater, grocery store, bus depot, train depot,Walmart. Convenience store 3 houses down. Skiing 20 mins away.

KitchenIndoor spacesGetting around

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.

4.9 out of 5 average rating, 249 reviews

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.

FamilyKitchenRiver

A spacious living area is presented with natural light filtering through large windows. Two brown sofas are positioned around a coffee table, and a decorative area rug adds warmth. A set of glass doors leads to the outdoor space, framed by cream-colored curtains.

4.95 out of 5 average rating, 104 reviews

Nice, Large Modern Apartment

Super clean, downstairs apartment with large spacious rooms. Great place with lots of room for fun! Perfect for the whole family, or just one person looking for space. 2 Bedroom, Living, Dining, fully stocked kitchen, large yard. Right in the heart of Rutland. Walking distance to Downtown Rutland and The Paramount Theatre. Quiet location. Keyless entry, air conditioning and fast WI FI. 15 min. to Killington. 30 min. to Okemo. Lots of hiking and biking trails and great golf courses nearby!

KitchenIndoor spacesBreakfast

Apartment in West Rutland

The rustic farmhouse is set on a spacious green lawn, showcasing a classic red exterior with a metal roof. Large windows provide ample natural light, and the surrounding trees create a serene country atmosphere.

Mountain View Apartment

Quiet, second floor, farmhouse apartment in country setting. Two connected bedrooms sleep four, one with a queen bed and the other with two twin beds. Watch the sunrise from the private deck or walk the fields to watch the sun set over the Adirondaks. Plenty of room to roam over the farm fields. Owner on property. 15 minutes from Castleton University. Please see more under "your property" -18 mi to Killington Resort/ 15 mi to Pico Ski Resort -9 miles to Rutland Regional Medical Center

Indoor spacesFamilyTV

4.92 out of 5 average rating, 143 reviews

4.98 out of 5 average rating, 163 reviews

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.

KitchenIndoor spacesParks

4.98 out of 5 average rating, 175 reviews

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.

KitchenFamilyBathroom

4.95 out of 5 average rating, 229 reviews

A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.

Guest suite in Clarendon

River House Apartment - Dog friendly

Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Indoor spacesFamilyBathroom

4.98 out of 5 average rating, 520 reviews

The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.

Castle in Clarendon

Kingsley Grist Mill Waterfall & Private Beach OMG

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

FamilyIndoor spacesWifi

4.94 out of 5 average rating, 116 reviews

Red Rooster Fall Foliage Hub Near Downtown Rutland

Welcome to The Red Rooster, a private second-floor guest suite in a historic 1867 Greek Revival Victorian with ample parking. Located on urban micro-farm, tucked into Rutland's Historic District, enjoy peaceful views and perfect urban convenience. Walk right to downtown dining, Amtrak, and the Paramount Theater! We are minutes from Killington Resort, Pico, the VAST trail, Appalachian Trail, and Lake Bomoseen. Your Green Mountain basecamp awaits.

KitchenFamilyLayout

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.

5.0 out of 5 average rating, 163 reviews

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.

FamilyIndoor spacesWifi

A vibrant bedroom features floral wallpaper and peach curtains. A spacious bed adorned with colorful pillows is positioned against one wall. Two windows allow natural light to fill the room. The pink door adds a cheerful touch, while a cozy chair is placed nearby.

4.86 out of 5 average rating, 294 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.

KitchenIndoor spacesSleep quality

The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.

4.96 out of 5 average rating, 701 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, skiing, golf, 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.

FamilyIndoor spacesSolo travel

Popular amenities for Rutland family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 112 reviews

An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.

Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

FamilyKitchenTV

4.88 out of 5 average rating, 177 reviews

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

KitchenIndoor spacesOutdoor spaces

A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.

4.94 out of 5 average rating, 308 reviews

Vermont Retreat, Dogs Welcome, Pool & Spa

Indoor spacesFamilyBiking

4.86 out of 5 average rating, 271 reviews

A serene view of a lake is framed by lush green trees and grass. The still water reflects the surrounding nature, while a patio area with seating is visible near the water's edge, inviting relaxation in a peaceful outdoor setting.

Home in Whitehall

Well appointed lakehouse. Peaceful family fun.

Indoor spacesKitchenHeating

4.96 out of 5 average rating, 224 reviews

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

KitchenFamilyWalkability

4.97 out of 5 average rating, 112 reviews

Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Indoor spacesFamilyView

4.93 out of 5 average rating, 152 reviews

A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.

Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Indoor spacesKitchenValue

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

4.79 out of 5 average rating, 337 reviews

Serene Top Floor Condo (resort style amenities)

KitchenIndoor spacesHot tub

Family- and pet-friendly home rentals

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.

4.94 out of 5 average rating, 126 reviews

Mountain Getaway Pet friendly

KitchenFamilyGetting around

Superhost

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

FamilyIndoor spacesBreakfast

4.87 out of 5 average rating, 283 reviews

4.94 out of 5 average rating, 476 reviews

The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.

Farm stay in Salisbury

Quaint 1-bedroom cottage on Blue Ledge Farm

FamilyIndoor spacesView

4.84 out of 5 average rating, 190 reviews

An old barn features weathered wooden siding and large windows, set against a backdrop of vibrant autumn foliage. A maple tree with bright orange leaves provides a natural canopy, while a carpet of fallen leaves covers the grassy ground, creating a serene outdoor scene.

Barn in Mount Holly

Mapleside Escape: Sugar/Ski/Green Mountains

Indoor spacesFamilyNearby

4.89 out of 5 average rating, 224 reviews

A stationary white bus sits on a gravel path surrounded by green grass. In the background, sparse trees and expansive fields are visible. Two outdoor chairs and a small shed can be seen nearby, highlighting the serene, rural setting.

Bus in Granville

Serene Bus Getaway Among Rolling Farm Land

Indoor spacesFamilySleep quality

4.91 out of 5 average rating, 1028 reviews

The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

KitchenIndoor spacesGrill

4.98 out of 5 average rating, 180 reviews

The cabin exterior features a two-story wooden structure surrounded by lush greenery. A stone patio with multiple seating options provides access to the lawn. Large windows enhance the views, while a balcony adds dimension to the facade.

Cabin in Comstock

East Cabin

FamilyIndoor spacesHeating

4.94 out of 5 average rating, 180 reviews

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

Cozy Contemporary Downtown Texaco

KitchenIndoor spacesBiking

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 115 reviews

A gravel road leads through open fields bordered by manicured greenery. In the distance, rustic buildings and trees with autumn foliage are visible against a clear blue sky, creating a serene rural landscape.

Farm stay in Clarendon

Dream Catcher Farm

KitchenIndoor spacesGetting around

A cozy living area features a stone fireplace, providing warmth and a focal point in the room. Two brown sofas are positioned around a coffee table. Soft lighting from a nearby lamp creates a comfortable ambiance, complemented by large windows letting in natural light.

4.93 out of 5 average rating, 503 reviews

Book Peep now Stay on Pico 1 Bedroom free shuttle

FamilyKitchenLocation

A view from the balcony showcases the surrounding landscape, highlighting green hills and clear blue skies. Two adjoining buildings are visible, featuring sloped roofs and a variety of architectural styles. The area appears tranquil, with open spaces and scattered trees enhancing the natural scenery.

4.95 out of 5 average rating, 216 reviews

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

Indoor spacesKitchenNearby

4.95 out of 5 average rating, 134 reviews

A spacious living room features a comfortable sectional sofa facing a propane fireplace. A mounted TV is positioned above the hearth. Natural light enters through sliding glass doors leading to a private porch, surrounded by lush greenery.

Condo in Mendon

Hotel Chic - Home Comfort -Ski Easy.

Indoor spacesKitchenSolo travel

Superhost

A cozy living area features a brick fireplace at its center, surrounded by two comfortable armchairs and a wooden coffee table. A Roku Smart TV is positioned next to large glass doors leading to the balcony, while a mirror reflects the warm ambiance. Natural light enhances the wooden accents on the walls.

4.84 out of 5 average rating, 188 reviews

Cozy Condo- Close to Mountain, Ski home trail

KitchenFamilyParking

4.94 out of 5 average rating, 107 reviews

A cozy living area features a spacious sectional sofa and a wooden coffee table, with candles placed on top. Artwork depicting mountain scenes decorates the wall, while a glass door leads to the private balcony, allowing natural light to brighten the space.

Condo in Mendon

¤5-15 Mins to Mountains & Trails | Fast WiFi¤

FamilyIndoor spacesParking

4.89 out of 5 average rating, 124 reviews

The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.

Condo in Mendon

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

KitchenFamilyCleanliness

Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.