Holiday rentals with a patio in Orange

5 out of 5 average rating, 109 reviews

The exterior of the country home is showcased, depicting a two-story structure with a welcoming porch. Lush green grass surrounds the house, and vibrant flowers bloom along a stone pathway, enhancing the natural beauty of the tranquil setting.

Home in Shelburne Falls

Charming Brookside Artisan Home

Relax, work & play in this peaceful country home built by a renowned furnituremaker and filled with handmade furniture and art. Explore the countryside, listen to the babbling brook & visit the many local family farms. There is a large firepit and plenty of outdoor activities at your doorstep, including biking, hiking, and x-country skiing. Come get away from it all while being only 10 minutes to Greenfield and the quaint village of Shelburne Falls. Easy 30 minute drive to the five college area.

4.98 out of 5 average rating, 119 reviews

An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.

Cabin in Stoddard

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Guest suite in Village of Pelham

4.99 out of 5 average rating, 139 reviews

Under the Hemlocks Escape: A Cozy Getaway Retreat

Escape to a tranquil, bijou studio retreat under the hemlocks—your perfect getaway. This scent-sensitive gem features elegant furnishings, quality linens, and thoughtful amenities. Enjoy the dreamy bed, custom kitchenette, and deep clawfoot soaking tub with rain shower. Relax by the indoor fireplace and unwind in your private outdoor spaces, including the unique Writer’s Retreat—an off‑grid rustic haven. Fast Wi‑Fi, parking, and minutes to UMass and Amherst—your restful, boutique escape awaits.

4.89 out of 5 average rating, 206 reviews

A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.

Home in Westminster

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Guest house in Cummington

A cozy sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.

5 out of 5 average rating, 140 reviews

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Guest suite in Hubbardston

A cozy living area is featured with a brown sofa adorned with patterned cushions. A small coffee table sits on a patterned rug, and a lamp is positioned beside a side table. In the background, the kitchen is visible, showcasing stainless steel appliances and additional cabinetry.

4.97 out of 5 average rating, 157 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

5 out of 5 average rating, 209 reviews

An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.

Loft in Peterborough

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

4.97 out of 5 average rating, 190 reviews

The exterior of a light blue guesthouse is framed by lush greenery and trees. A distinctive tower is visible atop the building. The setting conveys a sense of seclusion in a natural environment, with a glimpse of the yard in the background.

Cottage in Deerfield

Dreamy Guesthouse: sauna and private deck

You will feel like you're deep in the country while being close to everything on this 11-acre homestead, surrounded by woods. Featuring an infrared sauna, breezy porch, and firepit, this private guesthouse (next to our residence) is a 15-min walk to Deerfield Academy, Bement, Eaglebrook, and Historic Deerfield; a short drive to all five colleges; and less than three miles from award-winning Treehouse Brewery. Halfway between Brattleboro and Northampton, this is the perfect valley spot.

4.99 out of 5 average rating, 155 reviews

The treehouse stands elevated among tall trees, featuring a warm wooden exterior and large windows that allow natural light to fill the interior. A deck extends from the structure, leading to a fire pit area surrounded by gravel.

Treehouse in Putney

Treehouse Haven in Putney-All Seasons

Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting toilet ☽ Tea & local coffee ☽ Hot outdoor shower ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Visit for romance, time with the family, a retreat from the business of life, or even a remote work sanctuary.

4.99 out of 5 average rating, 161 reviews

Two white lounge chairs are positioned around a small black fire pit in a grassy area. Lush greenery and trees define the backdrop, while an open space creates a sense of privacy and tranquility.

Flat in Brattleboro

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

5 out of 5 average rating, 133 reviews

A well-maintained home is situated on a gentle slope, featuring a neatly landscaped front yard with flowering plants and shrubs. An American flag is displayed by the entrance, and a gravel driveway leads to the garage below, surrounded by lush greenery.

Home in Amherst

The Suprenant House

Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.

4.99 out of 5 average rating, 152 reviews

A welcoming porch features a decorative swing with two cushions and a small table, creating a serene space. Natural light filters through large windows, and colorful banners hang above, while a wooden structure nestles comfortably in the surrounding greenery.

Cabin in Guilford

Rustically Romantic Cabin Near Sweet Pond

COUPLES RETREAT, SOLO ESCAPES & WRITER'S DREAM in Southern Vermont - No Cleaning Fee Perfect for ENGAGEMENTS, HONEYMOONS & ANNIVERSARIES Authentic log cabin tucked into a private wooded cove outside of Brattleboro. A short tranquil walk to Sweet Pond State Park. Biking galore and Kayaking nearby. A variety of hikes to choose from. ROMANCE SPECIAL Stay 4-nights or more & receive hard cider, cheese & chocolate. Ask Me About ELOPEMENT & VOW RENEWAL CEREMONIES

Popular amenities for rentals with patio in Orange

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Flat rentals with a patio

4.96 out of 5 average rating, 123 reviews

A cozy bedroom features a black metal bed frame with a green quilted coverlet. Soft lighting is provided by two bedside lamps on wooden nightstands. A decorative wall clock and framed artwork enhance the space, with a woven chair adding texture to the room.

Flat in Northampton

Downtown 2BR 1.5 Bath Townhouse Charm

4.99 out of 5 average rating, 171 reviews

A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.

Flat in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

4.95 out of 5 average rating, 110 reviews

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Flat in Putney

Minimal organic hideaway inspired by nature

Superhost

A well-lit bedroom features a spacious bed adorned with a floral-patterned quilt. A daybed is situated next to a window, which offers a view of greenery outside. An armchair sits in the corner, complementing the light color scheme of the room.

Flat in Northampton

4.82 out of 5 average rating, 139 reviews

Florence ctr 1br apt near town, trails, river!

Superhost

An open-concept living and dining area is featured, with a wooden dining table surrounded by white chairs. A decorative area rug lies underneath. The adjacent living room is visible, showcasing a brown sofa, two armchairs, and various decorative wall art, all in a soothing color palette.

Flat in Charlemont

4.85 out of 5 average rating, 110 reviews

Spacious apartment close to skiing and rafting

4.85 out of 5 average rating, 155 reviews

The updated kitchen features modern appliances, including a black microwave and oven. Light-colored cabinetry contrasts with the granite countertops. A coffee maker sits on the counter, and a dining table is visible, providing a space for meals. The floor is covered with wood-like laminate.

Flat in Holyoke

Quiet bright & sunny 2 bedroom apartment w/ porch

4.96 out of 5 average rating, 119 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Flat in Otis

Enjoy every season the Berkshires have to offer.

5 out of 5 average rating, 126 reviews

A dining area features a wooden table surrounded by six chairs, complemented by a vibrant fruit bowl at the center. A bookshelf filled with various books stands nearby, while a wooden cabinet adds warmth to the room. Bright natural light filters through the windows.

Flat in Northampton

Charming retro retreat with vintage soaking tub

House rentals with a patio

5 out of 5 average rating, 16 reviews

Home in Jaffrey

Lucy's Lodge is your home away from home

4.98 out of 5 average rating, 89 reviews

A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.

Home in Jaffrey

Willow Falls Home ~Hot tub & Waterfront

5 out of 5 average rating, 10 reviews

Home in Northampton

Luxury 3BR home in the forest, mins from downtown

5 out of 5 average rating, 11 reviews

The interior space features large triangular windows that frame a view of the mountains and surrounding trees. Natural light fills the area, highlighting the wooden railing that borders the lofted space. Two small tables are positioned near the windows, enhancing the inviting atmosphere.

Home in Marlborough

4 BR Monadnock View Luxury Chalet

5 out of 5 average rating, 8 reviews

Home in South Deerfield

Serene South Deerfield Retreat

4.94 out of 5 average rating, 16 reviews

A charming entrance of the farmhouse is highlighted by a vibrant turquoise door. Two potted plants with colorful blooms flank the door, set against white siding and large windows that allow natural light to fill the space. The steps are framed by a simple wooden railing.

Home in Guilford

Farmhouse at Weatherhead Hollow

5 out of 5 average rating, 27 reviews

A spacious deck overlooks a vibrant sunset, with an expansive view of rolling hills and trees under a partially cloudy sky. The area is enclosed by modern railing, and the deck's surface provides ample space for relaxation or gatherings.

Home in Leyden

Mountaintop Views, close to private schools, golf

5 out of 5 average rating, 22 reviews

The exterior of the home is bathed in soft evening light, highlighting the warm wood tones of the siding. Cozy outdoor seating is arranged under string lights in the backyard, creating an inviting atmosphere. Lush greenery and ferns surround the area, enhancing the sense of tranquility.

Home in Amherst

Amherst Treehouse

Apartment rentals with a patio

A cozy living area is highlighted by a stone fireplace, featuring firewood neatly stacked beside it. A flat-screen TV is mounted above the mantel, with built-in cabinets on either side. A sectional sofa and wooden coffee table provide comfortable seating for relaxation.

5 out of 5 average rating, 24 reviews

Slopes N Seasons | Trailside Condo at Mount Snow

Apartment in Shelburne Falls

A spacious light blue deck is shown, furnished with a small table and two white chairs. The surrounding area features greenery and a distant view of rolling hills, providing a serene outdoor space for relaxation.

4.9 out of 5 average rating, 51 reviews

Flowers & Falls Spot House

4.92 out of 5 average rating, 38 reviews

The exterior of the lodge features a blend of stone and wood elements, with multiple balconies and large windows reflecting the surrounding landscape. The entrance is framed by a welcoming staircase, leading to the main doorway marked with a sign that reads 'Hardwood Lodge'.

Apartment in Stratton

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

A spacious living area is introduced, featuring a stone fireplace and a large sectional sofa arranged around a coffee table. A dining table and chairs are positioned nearby, with natural light filtering through large windows adorned with curtains.

4.94 out of 5 average rating, 77 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

5 out of 5 average rating, 16 reviews

Apartment in Stratton

Luxury Condo * 3BD/3BA * Fall Foliage

A cozy living room showcases two plush couches and a small wooden coffee table. A gas stove is nestled in a brick corner, while sliding doors offer views of the outdoors. Colorful lights frame the window, adding a touch of charm to the space.

4.91 out of 5 average rating, 57 reviews

Ski Condo 5 Min from Mt Snow

5 out of 5 average rating, 48 reviews

A snow-covered landscape reveals nearby mountains and ski slopes under a clear blue sky. Trees with bare branches frame the scene, while quaint buildings and a parking area are visible in the foreground, suggesting a vibrant ski village atmosphere.

Apartment in Stratton

Your Vermondo awaits: Steps to Lifts & Village.

A modern kitchen is showcased with white cabinets and a dark granite countertop. Stainless steel appliances, including a refrigerator and stove, are visible. A dining table with wooden chairs is situated nearby, while a cozy living area can be seen through the open layout.