
Holiday rentals with a patio in Chesterfield
Find and book unique rentals with patio on Airbnb
Quick stats about holiday rentals with a patio in Chesterfield

Total holiday rentals
Explore 20 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 970 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Wifi availability
20 of Chesterfield holiday rentals include wifi access

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

4.9 Average rating
Chesterfield stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with patio in Chesterfield
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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.

Peaceful Mill with Waterfall - 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 remote workspace

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

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 outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

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 .

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Cozy tent in the trees on organic flower farm
Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Minimal organic hideaway inspired by nature
Akasha, the first floor of this historic 1800’s carriage house in the center of Putney Village, was gutted and meticulously renovated by the hosts into a unique wellness apothecary and cafe and now serene and beautifully conceptualized open concept studio apartment. Aged wood tones, textured plaster walls, poured concrete counter tops and elegant dining bar imbue an old world tea house aesthetic with modern sensibilities. A unique space for quiet contemplation and relaxation.

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Discover the ultimate outdoor experience in Southern NH! Enjoy a year-round private hot tub in a covered gazebo, fire pit, hammock, life-size games, and swing set. Located in one of Keene’s safest, quietest neighborhoods, walking distance to downtown and across from Keene Ice Rink. Close to beaches, hiking, and ski resorts. Features a fully stocked chef’s kitchen, wine cooler, and luxury Purple mattresses with individual mini-splits in each bedroom for optimal comfort.

Luxury Glamping NH - Geodome Sanctuary
Escape to a private luxury sanctuary retreat tucked behind a small family owned Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, hammock and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 80 minutes from Boston, yet a world away.

Southern Vermont getaway
Spacious, comfortable and very large light-filled one bedroom all to yourselves. The single-story unit is attached to our lovely farmhouse but has a separate entrance. Hardwood floors, exposed beams and beautiful views of gardens and woods for a one-of a-kind retreat in beautiful Putney, VT. Close to skiing, hiking, and kayaking (45 min to Mt Snow, Okemo, Grafton ponds and more). Plenty of room for reading, TV, cooking, working or napping.

Guest House @ 120
Unforgettable designer stay in the heart of downtown Brattleboro. Curated art, luxe finishes, and boutique comfort set this experience apart. Walk to the best cafes, boutiques, and galleries. Enjoy a chef’s kitchen, plush bed, quaint bath, and fast Wi-Fi. Every detail is elevated, every corner styled. Steps from Amtrak, wrapped in Vermont charm. Perfect for escapes, retreats, or inspired work. You won’t want to leave.
Popular amenities for rentals with patio in Chesterfield
Flat rentals with a patio

Suite Sunset 311 Rice Lane Bennington VT

Berkshire Mountain Top Chalet

Cozy two bedroom near Manchester

Historic Victorian - Entire 3rd floor

10 Min to HITS Summer Fest/ 20 Min to Manchester

Suite 23 - Spacious Sunny 2-BR with Mountain view

"Nostalgia" a spacious2 bedroom first floor unit.

New England Escape
House rentals with a patio

Porcupine Hill Farm

Willow Falls Home ~Hot tub & Waterfront

Peaceful VT Mountain Retreat, Lg Deck & Fire Pit

Charming Brookside Artisan Home

Stone Ridge Cottage

Charming Chalet - Putney Village

Lakefront, view of ski mtn, firepit, kayaks, dock

Woodsy Retreat Near Skiing, Private Pool in Summer
Apartment rentals with a patio

Main St Escape | Explore Downtown Ludlow

Downtown Adams Vintage Getaway

Ski On/Off 2BR w/Pool, Fireplace & Arcade

Great Amenities-Season Condo gym-sport center-pool

Ski Condo 5 Min from Mt Snow

Fully Renovated 3 BR Condo - 0.8 mi to Mt. Snow

Ground Floor, Okemo True Ski-in/Ski-Out

Cozy Condo-4 Minute Walk to Skiing at Mount Snow!
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Rentals with outdoor seating Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a firepit Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with a patio Cheshire County
- Rentals with a patio New Hampshire
- Rentals with a patio United States
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- University of Massachusetts Amherst
- Mount Monadnock
- Mount Sunapee Resort
- Smith College
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Holyoke College
- Mount Greylock
- Camp Plymouth State Park
- The Montague Bookmill
- Jamaica State Park
- Crotched Mountain Ski and Ride
- Bridge of Flowers





