Chesapeake Bay Ski Chalets
Ski Chalet
10.0(10 Reviews)
5 Bedrooms
4 Baths
16 Guests
4000 ft²
Oceanfront
Hot Tub
Fireplace/Heating
Ocean View
US $763/Night
7 Nights - US $5,343
Ski Chalet
8.2(5 Reviews)
2 Bedrooms
1 Bath
9 Guests
1410.07 ft²
- Hot Tub
- Fireplace/Heating
Balcony/Terrace
Pet Friendly
US $382/Night
7 Nights - US $2,675
Ski Chalet
10.0(2 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
Kitchen
US $274/Night
7 Nights - US $1,921
New
Ski Chalet
2 Bedrooms
2 Baths
9 Guests
1408 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $281/Night
7 Nights - US $1,965
Ski Chalet
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
Air Conditioner
Child Friendly
Laundry
US $180/Night
7 Nights - US $1,261
Ski Chalet
4.8(5 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
US $257/Night
7 Nights - US $1,799
Bed & Breakfast
10.0(89 Reviews)
23 Bedrooms
24 Baths
60 Guests
- Balcony/Terrace
Parking- Air Conditioner
- Internet
US $289/Night
7 Nights - US $2,022
Bed & Breakfast
10.0(215 Reviews)
1 Bedroom
1 Bath
Spa
Pool- Balcony/Terrace
Breakfast
US $265/Night
7 Nights - US $1,856
House
10.0(402 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $382/Night
7 Nights - US $2,671
House
10.0(17 Reviews)
3 Bedrooms
2 Baths
7 Guests
1302.43 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $161/Night
7 Nights - US $1,127
Cottage
10.0(311 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $338/Night
7 Nights - US $2,364
Bed & Breakfast
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
398.26 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $232/Night
7 Nights - US $1,624
Why Choose Rent By Owner for your Chesapeake Bay Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Chesapeake Bay
How to Book Your Chesapeake Bay Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chesapeake Bay
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Chesapeake Bay, MD
Maryland
Northern Chesapeake Bay
Norfolk - Virginia Beach
Washington
District of Columbia
Virginia Beach
Northwest
Baltimore
Anne Arundel County
Accomack County
Northeast Virginia Beach
Alanton
Chesapeake Bay Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets in Chesapeake Bay?
There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Chesapeake Bay:
- Stay in the HEART of Saint Michaels!
- Cottage on a Private Island in the York River
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Summertime where the livin’ is easy at the Rivah in Irvington!
- Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
- Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.
- Captivating Chesapeake experience
- Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.
- Historic Cottage on Ware River Estate
- Private Apt. in Historic Home: Walk to Monuments, Museums & Convention Center.
2. How many Ski Chalets are available in Chesapeake Bay?
Currently, the total number of properties listed by RBO in 2026 is over 6 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Chesapeake Bay.
More Rentals You May Like Near Chesapeake Bay
Cottage
10.0(287 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $230/Night
7 Nights - US $1,609
House
10.0(8 Reviews)
3 Bedrooms
2 Baths
10 Guests
10763.91 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
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House
10.0(203 Reviews)
3 Bedrooms
2 Baths
10 Guests
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- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $446/Night
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House
10.0(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1237.85 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $425/Night
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Cottage
10.0(188 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
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Bed & Breakfast
10.0(8 Reviews)
1 Bedroom
2 Baths
6 Guests
850.35 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $318/Night
7 Nights - US $2,224
Cottage
10.0(168 Reviews)
2 Bedrooms
1 Bath
6 Guests
1300 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,746
House
10.0(160 Reviews)
2 Bedrooms
2 Baths
4 Guests
1425 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $371/Night
7 Nights - US $2,599
Cottage
10.0(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $867/Night
7 Nights - US $6,070
Cottage
10.0(133 Reviews)
2 Bedrooms
1 Bath
8 Guests
963 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $529/Night
7 Nights - US $3,706
House
10.0(116 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $190/Night
7 Nights - US $1,328
House
10.0(111 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $468/Night
7 Nights - US $3,274
