
Vacation rentals with a patio in Chester
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Top-rated patio rentals in Chester
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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!

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.

Fresh Snow- Luxury Cabin near Ski Areas
On a cold winter morning Wake up in a luxurious bed in a stylish cabin with panoramic Vermont views. Hot coffee mug warming your hand, step out to the porch, look at faraway hills. Snowshoe/slide/talk/play with your favorite people/animals. Or jump in your car to Okemo/Magic Montain/Killington for a day on the slopes. Take a scenic drive to Woodstock, Simon Pearce, Okemo, or the Harpooon Brewery. Kick back with a night around the firepit stargazing Our Red House welcomes you.

3BR 2BA Stratton Condo w/ Fireplace & Forest Views
Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

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.

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.
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

Walk to main lift! The Handle Studio @ Mt. Snow!

1BR Downtown-Walkable & Stylish
House rentals with a patio

Lakefront Retreat with Nearby Skiing

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

Vermont Ski and Stay

The Looking Glass, a modernistic escape

Relaxing Countryside Oasis!

Pristine Magical Retreat Cottage 15 min to Mt Snow

Lakefront Cottage near Sunapee-OHRV & Ice Fishing!

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain
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🏂❄️…

CozyCub- Location, Fireplace, Ski Off/Shuttle On!
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$46,789 GYD | G$52,011 GYD | G$44,073 GYD | G$38,642 GYD | G$38,434 GYD | G$38,851 GYD | G$41,149 GYD | G$41,776 GYD | G$41,358 GYD | G$49,086 GYD | G$52,219 GYD | G$56,606 GYD |
| 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 G$18,799 GYD 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 fireplace Chester
- Rentals with a fire pit 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
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Mount Sunapee Resort
- Dartmouth College
- Mount Monadnock
- Massachusetts Museum of Contemporary Art
- Southern Vermont Arts Center
- Emerald Lake State Park
- Camp Plymouth State Park
- Jamaica State Park




