Skip to content

Holiday rentals in Whaley Lake

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Whaley Lake

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

  1. Entire cabin
  2. Holmes
*Newly Renovated* Lakefront Escape with Views

A year-round waterfront home with gorgeous unobstructed views of Whaley lake provides the perfect escape for a long weekend or vacation. Enjoy swimming and lake activities via private direct lake access. Spacious boathouse deck for entertaining or sunbathing. Cozy up to a two-story stone fireplace while enjoying the fall and winter colors.

SUPERHOST
  1. Entire cottage
  2. Pawling
Country Cottage Getaway with Yoga Shed & Sauna

This country cottage, 5 minutes from the charming Village of Pawling, has just been renovated and is surrounded by a woodland stream on two sides. Master bedroom and full bath upstairs, small guestroom/office and half bath downstairs. Bright, cheery kitchen is stylish and functional. Yoga/meditation shed with sauna is situated on the edge of the wetlands about 100’ from the cottage. (Avail. through Oct). Visit the famous Pawling Farmers Market on Saturday's from mid-June to September 24th.

SUPERHOST
  1. Entire cabin
  2. Carmel Hamlet
Hudson Valley Lakefront privatedock @thatlakehouse

Welcome! If you're interested in a month long stay for February let us know! Our house sits on one acre with 100ft of waterfront. It is family and pet friendly, great for families or a romantic getaway from the city. In summer you can enjoy the kayaks and paddle board or fish and swim right from the dock. In the winter you can sled (or walk) from the deck all the way to the water or stay warm by the fireplace and enjoy the view. 75 minutes from NYC, 15 minutes from the Metro North.

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Other great holiday rentals in Whaley Lake

SUPERHOST
  1. Entire guest suite
  2. Holmes
2500 sq ft with prvt pool! 1.5hr from NYC
SUPERHOST
  1. Entire cottage
  2. Pawling
Forest Acres Cottage: Central Air Conditioning!
SUPERHOST
  1. Entire cottage
  2. Carmel Hamlet
Lakeview A-frame in the Trees - Hudson Valley
PLUS
  1. Entire cabin
  2. Pawling
Serene, Peaceful Cabin by the Lake
  1. Entire cabin
  2. Carmel Hamlet
Cozy cabin in beautiful White Pond Lake.
  1. Private room
  2. Pawling
Cozy room in safe neighborhood
SUPERHOST
  1. Entire rental unit
  2. Carmel
Private space, with yard
SUPERHOST
  1. Private room
  2. Pawling
Cozy retreat just a short stroll from the village
SUPERHOST
  1. Entire home
  2. Pawling
Farmhouse Oasis in the Hudson Valley, Stream Views
  1. Entire rental unit
  2. Patterson
Modern Country Farm
SUPERHOST
  1. Entire townhouse
  2. Hopewell Junction
Villa Scafuri
SUPERHOST
  1. Entire home
  2. Carmel Hamlet
☀️ 3 Bed Lake-Front Retreat, Stunning Views! ☀️
  1. Airbnb
  2. United States
  3. New York
  4. Dutchess County
  5. Pawling
  6. Whaley Lake