Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Guest favorite

Home in Wilmington

5 out of 5 average rating, 10 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Enjoy stunning lake & mountain views w/ easy access to hiking, swimming, boating, & fishing (kayaks, paddle board, and bikes included). Cathedral ceilings w/ beams provide a cozy feel & heated floors give an always-warm home in the winter. Covered deck w/ grill is great for outdoor dining. Additional features include outdoor hot tub, sauna, & quality game room (pool table, shuffleboard, foosball, ping pong). 4WD/AWD required in winter. Close to Mt. Snow & downtown Wilmington w/ shops and dining.

Guest favorite

A spacious living area features a central brick fireplace surrounded by built-in bookshelves. Light-colored sofas are arranged around a glass coffee table on a patterned rug, with large windows providing natural light and views of the outdoors.

Home in Old Chatham

4.96 out of 5 average rating, 25 reviews

Post and Beam Hilltop Sanctuary

Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 24 reviews

Luxury Redo: Hot Tub, Playroom, Sleeps 12

Creamery: Fully Renovated 5 Bedroom Home, sleeps 12 with large screened porch, outdoor patio with seating, sun umbrella, hot tub, fire pit and billiards! Amenities also include: Central AC, all new kitchen appliances, washer/dryer, 4 Smart tvs, fiber internet + good cell service, propane fireplace, blue stone outdoor patio with seating, billiards table, playroom, high quality linens included, Front porch with seating, superior central location: less than 10 to GB, less than 10 to Catamount!

Guest favorite

A wooden chair is positioned on a spacious deck, offering a view of the serene lake and surrounding greenery. A kayak is visible on the grass nearby, with the calm water reflecting the lush landscape.

Home in Athens

4.92 out of 5 average rating, 118 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

Chalet in Goshen

4.89 out of 5 average rating, 142 reviews

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & stunning woods view, 10 minute drive to Woodridge Lake.

Top guest favorite

An open door leads to a private balcony, where a serene tree offers shade. A large, relaxed dog rests on the balcony floor. Bright greenery is visible, enhancing the tranquil outdoor atmosphere.

Apartment in Wilmington

4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Top guest favorite

A serene evening scene features a private pool surrounded by trees, illuminated by soft garden lights. Lounge chairs and an outdoor dining area are thoughtfully arranged, while a fire pit invites relaxation. Lanterns guide the way along the pathway, enhancing the tranquil ambiance.

Home in Saratoga Springs

4.96 out of 5 average rating, 49 reviews

Pool w/Large Private Yard, SPAC,Town & Track Close

4th of July Weekend Available with discounted rates!! Clean, Comfortable, Peaceful retreat is waiting for you to book! All the comforts of home are included in our well appointed home that has distinct large areas for togetherness, yet fully separate spaces to retreat during rest time, each bedroom has it’s own vanity to get ready to go out on the Town! The backyard is your own private pool oasis! House is biking distance to SPAC & Park. We can't wait to share all of are updates with you!!

Guest favorite

A modern lakeside establishment is depicted, featuring a spacious outdoor seating area with umbrellas. The structure has large glass windows and a sleek design, while a sandy beach area is visible in the foreground, inviting guests to relax by the water.

Bungalow in Saratoga Springs

4.97 out of 5 average rating, 108 reviews

Home in Saratoga Springs

Recently Renovated Bungalow 2 Bedroom •1 Bath + Loft area Beautiful Downtown Saratoga Springs is just 1 mile away where you will find casual & fine dining, cafes, shopping, & entertainment The Saratoga Racetrack, Congress Park , Saratoga Racino, Saratoga Performing Arts Center, Saratoga Lake , Golf Course, State Park , & Skidmore College are all within a 10 min. drive. This is also the PERFECT location for a short drive to Lake George/ Adirondack attractions as well as Ski Resorts

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favorite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Top guest favorite

A serene outdoor deck features a centrally placed Solo Stove surrounded by five wooden Adirondack chairs. The scene captures a tranquil sunset with soft pink and orange hues reflecting off distant mountains and lush greenery.

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Superhost

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.