
Holiday rentals with a patio in Chester
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Top-rated rentals with patio 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

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”.

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.

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.

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.

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.

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.
Popular amenities for rentals with patio in Chester
Flat rentals with a patio

Suite Sunset 311 Rice Lane Bennington VT

Grafton Homestead: Welcoming Couples & Solo Guests

Berkshire Mountain Top Chalet

Lovely Duplex with Deck and Central Location

Historic Victorian - Entire 3rd floor

Cozy two bedroom near Manchester

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

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT
House rentals with a patio

Ski home to Trail Creek!

Ski-In/Ski-Out Hike Okemo Mountain Condo

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

Ski Ready! Play Area, Crib, 11 Acre Farmhouse

Remington Ridge

Fresh Snow- Luxury Cabin near Ski Areas

Forest Lake Cottage: A Sweetwater Stay

Chester Mountain View
Apartment 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

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

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Ski Condo 5 Min from Mt Snow

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

Luxury, downtown apt w/ balcony close to skiing
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $288 SGD | $320 SGD | $271 SGD | $238 SGD | $237 SGD | $239 SGD | $253 SGD | $257 SGD | $255 SGD | $306 SGD | $257 SGD | $302 SGD |
| 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 holiday rentals with a patio in Chester

Total holiday rentals
Explore 60 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $116 SGD per night before taxes and fees

Verified guest reviews
Over 2,430 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Chester holiday rentals include wifi 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!
Destinations to explore
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- House rentals Chester
- Family-friendly rentals Chester
- Pet-friendly rentals Chester
- Rentals with a fireplace Chester
- Rentals with outdoor seating Chester
- Rentals with a firepit Chester
- Rentals with a washing machine and dryer Chester
- Rentals with a patio Windsor County
- Rentals with a patio Vermont
- Rentals with a patio United States
- Okemo Mountain Resort
- Stratton Mountain
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Fox Run Golf Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- The Shattuck Golf Club
- Willard Mountain
- Brattleboro Ski Hill
- Autumn Mountain Winery
- Clarksburg State Park




