
Vacation rentals with a patio in Chester
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Top-rated patio rentals in Chester
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Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 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

Pine Ridge Log Cabin Minutes to Okemo & Killington
Get away to Pine Ridge Cabin! A secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your morning coffee on the large wrap around deck overlooking Elm Brook before your day hiking, brewery hopping, or hitting the slopes! The cabin provides open floor plans centered around the large stone face fireplace, the perfect space for gatherings of family, friends, or a couples retreat! Pine Ridge Cabin is only a few minutes to town, shopping, restaurants, bars, and spa!

The Round House on the Connecticut River
"River Round" offers guests the finest waterfront on the New Hampshire side of the Connecticut River with a private dock, panoramic views, and spectacular sunsets. A four-season destination close to skiing at Okemo, Stratton, Sunapee and more. Circular main floor with cathedral ceilings, exposed beams, and a fully-equipped chefs kitchen along with three bedrooms and three baths. Walk-out basement holds a large bar and kitchenette, two additional bedrooms and full bath. Enjoy life on the River!

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!

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Private guesthouse in Lebanon
This cozy one-room guesthouse is located on a quiet street off the green in downtown Lebanon, NH. It offers a private entrance with access to a lovely outdoor patio and gas grill. The room has high ceilings, a full-sized bed, a bathroom/shower, and a kitchenette with coffee maker, electric kettle, microwave, toaster, and compact fridge. A short walk away from restaurants and cafes and a 12-minute drive to Dartmouth College. Please note that there is no kitchen sink or stove.

Ski Back to Trail Creek!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

Lovely 1-Bedroom condo with indoor fireplace!
This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

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.

Quaint stone house!
⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

Barrel Sauna + Hot Tub & Mtn Views
Escape to Stratton Chalet, 5 mins from a pristine swimming pond, featuring a new hot tub and barrel sauna with incredible Stratton mountain views. Recently renovated, Stratton Chalet features a large stone fireplace, outdoor, modern fire-pit area, two outdoor decks, contemporary outdoor furniture, Bose soundbar, and a well-equipped kitchen.
Popular amenities for Chester patio rentals
Apartment rentals with a patio

Suite Sunset 311 Rice Lane Bennington VT

Grafton Homestead: Welcoming Couples & Solo Guests

Lovely Duplex with Deck and Central Location

Cozy two bedroom near Manchester

Vermont Ski / Okemo / Killington / Pico / Stratton / Bromley

River View apartment

Minimal organic hideaway inspired by nature

Walk to main lift! The Handle Studio @ Mt. Snow!
House rentals with a patio

Lakefront Retreat with Nearby Skiing

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

Killington/Okemo, 7p Hot tub, Spacious, Mtn.views!

Vermont Ski and Stay

The Looking Glass, a modernistic escape

Relaxing Countryside Oasis!

Stratton; 8 min! Swimming, 2 min. Pet friendly

The Hideaway
Condo rentals with a patio

Main St Escape | Explore Downtown Ludlow

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Walk to Dining, Arcade & Bar- 5 Min to Mt. Snow

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

POW value in this Cozy 2 Bedroom .2 mi to lift

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

Ground Floor, Okemo True Ski-in/Ski-Out
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ823 | ﺩ.ﺇ914 | ﺩ.ﺇ775 | ﺩ.ﺇ679 | ﺩ.ﺇ676 | ﺩ.ﺇ683 | ﺩ.ﺇ723 | ﺩ.ﺇ735 | ﺩ.ﺇ727 | ﺩ.ﺇ863 | ﺩ.ﺇ918 | ﺩ.ﺇ995 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals with a patio in Chester

Total vacation rentals
Explore 60 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 2,590 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 of Chester vacation rentals include wi-fi access

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

4.9 Average rating
Chester stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a fire pit Chester
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- Rentals with outdoor seating Chester
- Pet-friendly rentals Chester
- Rentals with a fireplace Chester
- Rentals with a patio Windsor County
- Rentals with a patio Vermont
- Rentals with a patio United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art
- Mount Monadnock
- Emerald Lake State Park
- Camp Plymouth State Park
- Quechee Gorge




