Chesterfield showing autumn leaves, tranquil scenes and forest scenes

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Vacation Homes in Chesterfield

Relax in a serene space with a comfortable armchair, console table, and lush greenery.

"Easy stay, good location for us. Would stay again. "

$180 nightly

Aug 10 - Aug 11

Total includes taxes and fees

Enjoy cooking in this kitchen with a brick fireplace, large island, and modern appliances.

"Beautiful property "

Stunning multi-level space with a grand staircase, exposed beams, and a vaulted ceiling.

"We had a wonderful stay here over three nights in mid-April. We loved the style and personal touches of the property, and our dog loved how dog friendly it was and especially loved being able to prance around the beach and pull sticks out of the lake. Our visit was fantastic, and we’d happily come back sometime — well worth it!"

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and oven, surrounded by dark cabinetry and a wooden countertop.

"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "

$443 nightly

Aug 11 - Aug 12

Total includes taxes and fees

Relax in this inviting living room with a stone fireplace, large windows, and comfortable seating.

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

Relax in this serene space with a bed against the wall, flanked by windows and a cozy seating area.

Enjoy meals and games in this kitchen with a central island and pool table.

"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"

$333 nightly

Aug 10 - Aug 11

Total includes taxes and fees

Laundry room with washer and dryer, adjacent to a patio area with outdoor seating.

"Perfect little spot for a ski trip to Stratton!"

Escape to a serene oasis surrounded by lush greenery and a tranquil river view.

"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...

Kitchen features a central island, dining area, and window with outdoor views.

"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"

Cozy cabin interior with a central staircase, living area, and bedroom, perfect for relaxation and casual gatherings.

"We really appreciated the solitude and quiet retreat this cabin offered. "

Escape to a serene oasis surrounded by lush greenery and a tranquil river.

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

$256 nightly

Aug 18 - Aug 19

Total includes taxes and fees

Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, microwave, and sink.

"House was awesome! Fit a large group well! Would recommend for sure!"

Relax in this inviting living room with a round coffee table, plush armchairs, and a cozy sofa.

Relax in a serene outdoor space with three Adirondack chairs surrounding a planter.

"Very clean, well equipped and thoughtfuly supplied. An extra bonus were the great assortment of books, games, movies, and puzzles available. A great deal of experience and generosity went into choices made, and it was much appreciated. "

Kitchen features a double oven, microwave, and gas range, with a window above the sink.

"Stayed at this lovely home for a short weekend trip in the winter. Very convenient location, clean and well kept. Be sure to have AWD and proper tires if you visit in the winter!"