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Vacation rentals in Chester-Chester Depot

Vacation rentals in Chester-Chester Depot

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester-Chester Depot

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Queen Room with private bath
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Queen Room with private bath

    The Blue Spruce room contains one queen bed and is suitable for 1 or 2 guests. All of our guest rooms feature crisp 100% cotton sheets, fluffy duvets, pillow top mattresses, and restored antique furniture, and private bath with shower.

    What guests are saying:

    “The room, bathroom and house were just as pictured and very clean. We only stayed 1 night but the hospitality was outstanding and they even made us breakfast to accommodate our dietary needs, which was much appreciated! 20 minutes to Okemo and we walked to the Pizza Stone restaurant right next door for dinner which was excellent. We will definitely be back!”

  • Queen Room 3 with Private Bath
    SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
    Queen Room 3 with Private Bath

    The White Oak room contains one queen bed and is suitable for 1 or 2 guests. All of our guest rooms feature crisp 100% cotton sheets, fluffy duvets, pillow top mattresses, and restored antique furniture, and private bath with shower.

    What guests are saying:

    “I think aside from a blow-dryer we had everything we needed in this quaint and simple inn. Breakfasts were delicious, cooked by the host herself each morning, and we sincerely appreciate being allowed to check-in late and leave an hour past check out as well due to the storm. If you're considering local inns look no further- and be sure to check out MacLaomainn's Tavern for tasty cider and burgers just around the corner- open till midnight! I'm biased, but for anyone who cares about sustainability like I do, this place has a keen mind to it. Cheers, and thank you again.”

  • Secluded, elegant home w/ a furnished deck - close to skiing!
    Farm stay · 6 guests · 3 beds · 3.5 bathrooms
    Secluded, elegant home w/ a furnished deck - close to skiing!

    The health and safety of our guests, homeowners, and employees is our number one priority. Many of our vacation rentals minimize person-to-person contact with private amenities and entry via smart locks or lockboxes. Plus, each reservation is backed by 24/7 customer support and expert cleaning in line with current CDC guidelines.

    What guests are saying:

    “Fantastic place and even better host. Super well organized with information, amenities, and style. Top of the line design and finishings. Boutique hotelish but with a gourmet kitchen with all the extras. Every detail thought of by the host. Super easy and enjoyable. Great place.”

Holiday rentals for every style

Get the amount of space that is right for you.

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  • Unique stays

Popular amenities for Chester-Chester Depot holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester-Chester Depot

Historic Riverbend Colonial- Blue Room
SUPERHOSTPrivate room
Historic Riverbend Colonial- Blue Room
Price:€113 / night
Two Beautiful Bedrooms in Mountains
SUPERHOSTEntire flat
Two Beautiful Bedrooms in Mountains
Price:€88 / night
Quad Room with private bath
SUPERHOSTPrivate room
Quad Room with private bath
Price:€95 / night
Stone House Bed & Breakfast - Clark Room
SUPERHOSTPrivate room
Stone House Bed & Breakfast - Clark Room
Price:€60 / night
Historic  Riverbend  Colonial -  Princess Bedroom
SUPERHOSTPrivate room
Historic Riverbend Colonial - Princess Bedroom
Price:€122 / night
Country Refreshment minutes from Chester town
SUPERHOSTPrivate room
Country Refreshment minutes from Chester town
Price:€70 / night
Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!
Entire house
Bright, open home w/ wrap-around deck & mountain views - 2 miles to skiing!
Price:€208 / night
MOUNTAIN FUN HIDEAWAY!!  OKEMO-LUDLOW-VAST
SUPERHOSTEntire house
MOUNTAIN FUN HIDEAWAY!! OKEMO-LUDLOW-VAST
Price:€206 / night
Vermont Secluded Get Away
SUPERHOSTEntire house
Vermont Secluded Get Away
Price:€307 / night
Historic River Room
SUPERHOSTPrivate room
Historic River Room
Price:€102 / night
Cozy Guest Suite in the Mountains - The Fox & Owl
SUPERHOSTPrivate room
Cozy Guest Suite in the Mountains - The Fox & Owl
Price:€87 / night
One Bedroom Suite Near Okemo
SUPERHOSTEntire apartment
One Bedroom Suite Near Okemo
Price:€148 / night
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