Holiday rentals with outdoor seating in Rutland

4.89 out of 5 average rating, 205 reviews

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, Spacious, Mtn.views!

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.

Guest suite in Lake Bomoseen

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

4.97 out of 5 average rating, 231 reviews

My house is your house!

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.

4.94 out of 5 average rating, 117 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.

Apartment in Mendon

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS ❄️Killington - 15 minutes ❄️Pico - 5 minutes ❄️WIFI❄️QUIET❄️FIREPLACE ❄️COMFY❄️IMMACULATE ❄️SUPERHOST RATED OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes 🥾Minutes from LT/AT 💍Wedding Venues 🚴Mtn Biking •Squeaky Clean •Fireplace, WIFI •TV in living room & bedroom •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

4.9 out of 5 average rating, 106 reviews

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.

Flat in West Rutland

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. Forty minutes to ski areas, less to nearby lakes or Castleton University. Owner on property. -18 mi to Killington Resort/ 15 mi to Pico Ski Resort -9 miles to Rutland Regional Medical Center

4.95 out of 5 average rating, 331 reviews

An open living space is captured, featuring a comfortable couch, a colorful chair, and a round coffee table. Natural light brightens the room, highlighting a kitchenette area and coordinating furnishings across the suite. High ceilings contribute to an airy atmosphere, creating a welcoming environment.

Flat in Clarendon

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.

4.95 out of 5 average rating, 310 reviews

Home in Clarendon

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

5 out of 5 average rating, 144 reviews

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.

4.85 out of 5 average rating, 228 reviews

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.

Flat in Rutland

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.

4.98 out of 5 average rating, 492 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, Fall & Winter Wunderland, 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. Come make history with us ! Near Killington & Okemo Mtns.

4.97 out of 5 average rating, 357 reviews

A living area features a light grey sofa adorned with two decorative pillows, situated on a textured area rug. A wooden dining table and black chairs are visible nearby, while a wall-mounted sign adds a personalized touch to the warm-toned space.

Guest house in Castleton

Bomoseen Bungalow

Located near Lake Bomoseen and Castleton University. This is a charming upstairs apartment in a quiet, residential neighborhood. Walking distance to boat rentals and to a local country store. This apartment provides you with a cozy stay - a bedroom with a queen size bed, sofa bed, and air mattress. There is Roku television, a heat pump for air conditioning or heat, Keurig coffee maker, and more. This is a non smoking unit.

4.94 out of 5 average rating, 369 reviews

A two-story, white wooden house is surrounded by lush greenery and shrubs. A porch with a small seating area is visible, along with an air conditioning unit installed on the upper level's front wall. The bright sky and soft clouds provide a picturesque backdrop.

Flat in Poultney

Cozy Poultney Village Apartment

I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

4.99 out of 5 average rating, 123 reviews

Elegant Alpine Condo

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Sleeps up to 4 with a king bed and queen pullout sofa. Killington Reg #007718

Popular amenities for outdoor seating rentals in Rutland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.96 out of 5 average rating, 539 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

Cozy Bow House Perched in Trees w/ Hot Tub & View

4.98 out of 5 average rating, 429 reviews

A unique house constructed from reclaimed wood features a distinctive round shape and a metal roof. The natural stone fireplace is visible on one side, while large windows allow for ample light and views of the surrounding greenery.

Home in Tunbridge

The Barnbrook House

5 out of 5 average rating, 119 reviews

Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.

Home in Ludlow

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

5 out of 5 average rating, 474 reviews

A charming cottage is surrounded by a grassy area, featuring a red umbrella over a small outdoor table and chairs. Two white lounge chairs are positioned nearby, complemented by greenery and tall trees in the background.

Home in East Middlebury

Nice one bedroom cottage

4.84 out of 5 average rating, 312 reviews

A serene outdoor setting features a two-story house surrounded by greenery. A small pond reflects the landscape, while a fire pit is visible nearby. Rustic wooden chairs provide seating, and smoke can be seen rising from the fire, creating a cozy atmosphere in nature.

Home in Goshen

Nature Lover's Paradise

4.91 out of 5 average rating, 302 reviews

A spacious deck features wooden flooring and railing, surrounded by trees. Two wooden lounge chairs face a breathtaking view of the Green Mountains, providing an open space to relax and enjoy the natural scenery.

Home in Rochester

Mountain Home ready for you!

4.98 out of 5 average rating, 157 reviews

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

Home in West Windsor

Birdie's Nest Guesthouse

4.91 out of 5 average rating, 141 reviews

A cozy bed is adorned with an assortment of pillows in various colors, inviting relaxation. A tray on the bed holds a kettle, two mugs, and a small vase with greenery, while sunlight filters through curtains, illuminating the serene winter landscape outside.

Home in Mount Holly

Newly renovated. Minutes to Slopes & Trails

Apartment rentals with outdoor seating

4.75 out of 5 average rating, 170 reviews

The exterior view features a two-story gray house with white trim and red front doors. A well-maintained lawn surrounds the property, with a concrete pathway leading to the entrance. Tall trees provide a green backdrop, enhancing the inviting entrance.

Flat in Wallingford

Cozy Suite for 2 "Suite P"

4.85 out of 5 average rating, 172 reviews

A vibrant autumn landscape is captured, featuring a variety of trees adorned with bright orange, red, and yellow leaves. A winding river is visible in the foreground, surrounded by the lush greenery of the season. Overcast skies provide a soft light over the scene.

Flat in Bristol

Overlook at the Office

4.95 out of 5 average rating, 103 reviews

A modern kitchen features sleek white cabinetry and open shelving displaying glassware and kitchen essentials. A wooden dining table with black chairs provides a gathering space. Stainless steel appliances, including an oven and microwave, complement the stylish design, while a fresh plant adds a touch of greenery.

Flat in Ludlow

Peaceful Ludlow Base 5 minutes to Okemo

4.97 out of 5 average rating, 111 reviews

A charming Victorian home is framed by vibrant autumn leaves and colorful seasonal decorations. Two yellow doors invite guests, while pumpkins and chrysanthemums adorn the entrance steps. A friendly dog sits on the porch, adding a welcoming touch to the picturesque setting.

Flat in Salem

Yellow Door Inn

4.99 out of 5 average rating, 164 reviews

A spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.

Flat in Middlebury

Bluebird Studio- Light filled and airy

4.98 out of 5 average rating, 264 reviews

A cozy living space is presented with a light-colored sofa and a brown accent chair, complemented by a wooden coffee table. Shelving is visible in the background, showcasing decorative items, while a dining area with metal chairs can be seen in the distance.

Flat in Manchester

Style and Comfort- Perfect Year Round Location

4.99 out of 5 average rating, 192 reviews

A pathway of stone steps meanders through a lush green lawn, flanked by vibrant red geraniums in terracotta pots. Tall trees provide shade, creating a serene atmosphere, while a wooden bench invites relaxation amidst the surrounding nature.

Flat in Dorset

Vermont barn apartment

4.86 out of 5 average rating, 113 reviews

A blue house is nestled among vibrant autumn foliage. A directional sign labeled 'Skyeship House' points the way along a gravel path leading towards the front entrance, framed by trees showcasing warm seasonal colors.

Flat in Bridgewater

Killington Skyeship 4 BR | 1 Min Gondola + Hot Tub

Apartment rentals with outdoor seating

4.88 out of 5 average rating, 112 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.

Apartment in Mendon

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

A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.

4.92 out of 5 average rating, 179 reviews

Renovated unit, prime location! Shuttle on/Ski off

A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.

4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

4.85 out of 5 average rating, 137 reviews

A spacious sleeping area features a large bed with a textured gray coverlet, complemented by two decorative pillows. Flanking the bed are wooden nightstands with lamps. A wall art piece consisting of circular shapes adds visual interest, while natural light filters in through the nearby window.

Apartment in Ludlow

Okemo Clock Tower Base Ski-in/Ski-out Condo

A cozy living room features a large gray sectional sofa and plush armchair, inviting relaxation. A wooden coffee table sits in the center, with a textured throw draped casually over it. Natural light streams through multiple windows, enhancing the welcoming ambiance of the space.

4.99 out of 5 average rating, 118 reviews

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

4.94 out of 5 average rating, 105 reviews

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Apartment in Stratton

Great 2 bedroom condo at Stratton Mountain

4.79 out of 5 average rating, 121 reviews

The living area features a soft gray couch and a black lounge chair, complemented by a textured area rug. Natural light enters through a large window dressed with light curtains. A wooden cabinet and an art piece with an animal illustration are also present.

Apartment in Warren

Modest Mountain Dacha

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.