Holiday rentals with a patio in Chester

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Chester

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Killington

4.95 out of 5 average rating, 130 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

5–12 Aug

$136 SGD per night

Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 120 reviews

Mi Casa es su Casa!

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 TV, surround sound system. Wi-Fi access. 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. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

27 Jul – 3 Aug

$153 SGD per night

Guest favourite

Cabin in Newfane

4.95 out of 5 average rating, 106 reviews

Cozy Cabin in Southern VT

Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed. We can usually provide a travel crib if requested in advance.

24–31 Jul

$248 SGD per night

Guest favourite

Loft in Peterborough

5.0 out of 5 average rating, 100 reviews

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.

18–25 Jun

$361 SGD per night

Guest favourite

Home in Chester

4.92 out of 5 average rating, 26 reviews

Private Home in Chester, VT

Escape to our picturesque house in historic Chester, Vermont. Tucked away at the end of a private lane, this charming retreat offers a swimming pond, incredible views, a chef's kitchen, and 3 bedrooms. With high ceilings, a covered stone patio, laundry facilities, and amenities like air conditioning and heated floors, it's perfect for family gatherings or secluded getaways. Close to Okemo Mountain Resort and the many charms of Southern Vermont, this is an ideal destination for all seasons.

19–24 May

$361 SGD per night

Guest favourite

Cabin in Londonderry

4.96 out of 5 average rating, 101 reviews

Summit view cottage: Secluded cabin with hot tub

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 6 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.

1–8 Apr

$551 SGD per night

Guest favourite

Cottage in Newfane

4.99 out of 5 average rating, 176 reviews

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”.

25 Jan – 1 Feb

$211 SGD per night

Guest favourite

Tiny home in Chester

5.0 out of 5 average rating, 82 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

19–26 Apr

$348 SGD per night

Guest favourite

Apartment in Ludlow

4.93 out of 5 average rating, 55 reviews

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

Put your gear on the patio and just walk out to the slopes! Okemo Mountain Lodge ground floor unit. C-building is the closest property to the A-Quad/B-Quad lift. Come enjoy convenient skiing, free parking and fast internet. Ski school gathers right outside the patio. How convenient it is to make your own meal during a powder day! Please note there is no AC at this condo complex summer time. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

9–16 May

$133 SGD per night

Guest favourite

Guest suite in Chester

4.93 out of 5 average rating, 14 reviews

Stone Village Private Studio

Located in the Stone Village of Chester, VT. Our studio apartment is in one of the oldest homes built in 1835. Located 20 minutes to Okemo and Magic Mountain. Stratton is about 45 minutes away for our downhill/outdoor enthusiasts and we are centrally located for antiques and yummy food! Our cozy studio features a comfy queen size bed, fully stocked kitchen and bathroom with shower. Our living space features 2 arm chairs, an electric fireplace and a large screen TV.

15–22 Dec

$221 SGD per night

Guest favourite

Home in Chester

4.94 out of 5 average rating, 18 reviews

Getaway at Great Brook

Take a break and unwind at this peaceful dirt road getaway. If you would like to venture out to one or more of the multiple ski resorts surrounding the Chester area or just take a nice walk down the quiet dirt road while you stay. We would additionally like to recommend checking out the village of Chester and see what the little shops have to offer. Recently added great wifi through Vtel if you're looking to work remotely while enjoying some peace and quiet.

29 Jun – 6 Jul

$237 SGD per night

Guest favourite

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 127 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

7–14 Aug

$126 SGD per night