Vacation rentals in Whaley Lake

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Whaley Lake

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

4.94 out of 5 average rating, 181 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

Guest favorite

A dining area is shown with a round wooden table at the center, adorned with a vase of flowers. Large glass windows frame a serene lakeside view, with blooming flowers in the foreground and lush greenery. Soft sunlight reflects off the water, creating a tranquil atmosphere.

Home in Carmel Hamlet

4.92 out of 5 average rating, 190 reviews

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

Top guest favorite

A spacious area features large sliding glass doors leading to a private deck with two chairs. Natural light fills the space, enhancing views of the surrounding forest. Two windows on either side frame the outdoor scenery, creating an inviting atmosphere.

Apartment in Pawling

5 out of 5 average rating, 86 reviews

Quiet Studio Apartment in Pawling

For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

Superhost

A wooden deck is surrounded by lush greenery, featuring two lounge chairs positioned for relaxation. A charming cabin stands in the background, accentuated by a mix of trees and plants that create a secluded atmosphere.

Cottage in Carmel Hamlet

4.83 out of 5 average rating, 160 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

⸻ A cozy, art-filled cabin just over an hour from NYC, steps from a swimmable lake. Decorated with unique treasures collected from around the world, it’s a soulful space made for rest & reconnection. Enjoy a stone fireplace, fenced yard for pups, starry nights by the fire pit & peaceful mornings on the deck. Hike nearby trails & slow down. This isn’t just a cabin — it’s a story-filled retreat designed to help you rest, relax and rediscover what matters. Come for the lake. Stay for the magic!

Top guest favorite

An outdoor seating area is set among trees, featuring stone pathways and a gravel surface. A circular fire pit is surrounded by seating, and a small dining set with two chairs is positioned nearby. A grassy space adds greenery to the tranquil setting.

Guesthouse in Mahopac

4.95 out of 5 average rating, 235 reviews

Lakeview Guesthouse with Sauna

Art and light filled spacious studio with panoramic views overlooking lake Mahopac perched on a steep hill. A short 5 min walk down the hill to swimming/paddleboarding/canoeing. Walkable to an on-the-lake restaurant/ dining/ takeout options + boba tea! Drivable to farm fresh food markets, restaurants and art museums. Cedar dry Sauna on property for use. Nearby towns and hikes include Fahenstock Park, Pound Ridge, Cold Spring, Beacon, Ridgefield, or walk up the hill to trails of Volz park!

Top guest favorite

A wooden deck features a single reclining chair positioned on a patterned area rug. The space is surrounded by a wooden railing, providing views of the tranquil lake and lush greenery in the distance.

Cottage in Holmes

5 out of 5 average rating, 20 reviews

The Whaley Lakeside

Unwind at our newly renovated two-story lakefront getaway nestled on the shores of beautiful Whaley Lake. Just 80 minutes from NYC, it's the ideal weekend escape for families, couples, and friends—dogs included! Spend summer days kayaking, swimming, or dipping your toes off your private dock. Two spacious decks provide the perfect setting for morning coffee, evening cocktails, or just soaking in the peaceful lake views. And our new generator means everything works even in stormy weather!

Superhost

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment in Newburgh

4.86 out of 5 average rating, 188 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guest favorite

A handcrafted wooden staircase features unique railing posts made from natural branches. The rustic feel is enhanced by warm wood paneling that surrounds the staircase. A window allows natural light to filter in, illuminating the organic textures and shapes of the wood.

Cottage in New Milford

4.95 out of 5 average rating, 203 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favorite

A wooden dock leads up to the hillside cabin, bordered by lush greenery. Two paddleboards are securely positioned on the dock, alongside white Adirondack chairs. A fire pit sits on the dock, enhancing the lakeside retreat's inviting ambiance.

Cabin in Holmes

4.97 out of 5 average rating, 35 reviews

A View From the Lakehouse

Welcome to paradise! Come meet your family’s new favorite vacation home, where your backyard is Dutchess County's largest private motorboat lake and your commute is less than 90 minutes from Manhattan. Lounge in the sun on our private dock, explore all the lake has to offer on our state of the art fiberglass paddleboards, and take in the stunning views from this beautifully renovated cabin, tucked away on a hillside amongst the lush foliage. Come enjoy lakeside living at its finest!

Guest favorite

The interior of a compact living space is shown, featuring a bright red refrigerator adorned with photos. A modern stove and washing machine are visible, alongside wooden cabinetry. Natural light filters through large windows, illuminating the wooden ceiling and highlighting the cozy, functional layout.

Bus in Hopewell Junction

5 out of 5 average rating, 8 reviews

BIG RED the Bus at Menlo Pond

You'll love this unique and romantic escape. BIG RED with its 100% off grid capabilities, has travelled the country, giving the owner the great opportunity to explore the US. It's now tucked away, parked and here at Menlo Pond waiting for you to experience and enjoy the comfort of all it has to offer: *Queen size bed *Large couch *Full bath *Full stove/oven *Air conditioning *Large sink *concrete countertop *Butcher Block *outside picnic table, Barbque and small fire pit

Top guest favorite

A serene view of the Hudson River during sunset, showcasing vibrant hues of orange and pink reflecting on the water. Silhouettes of trees and hills frame the scene, creating a peaceful setting. The landscape reveals a quiet area with foliage and distant trees along the riverbank.

Home in Wappingers Falls

4.93 out of 5 average rating, 220 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Top guest favorite

A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.

Treehouse in Wallkill

4.99 out of 5 average rating, 313 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Whaley Lake vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Whaley Lake

A spacious boathouse deck extends over the water, featuring lounge chairs arranged for relaxation. A shaded picnic table invites outdoor dining. Lush greenery surrounds the area, offering a serene view of the lake and verdant hills in the background, captured under clear blue skies.

Cabin in Holmes

4.87 out of 5 average rating, 102 reviews

Charming Lakefront Escape with Views

KelseyRating, 5 stars2 weeks ago

We loved our stay here. 8 people and our pups fit comfortably in this cabin. The beds were comfortable and had everything we needed. Unfortunately the rain kept us inside for our trip but there were plenty of games to keep us occupied inside. The kitchen is small but the space is used very well and has everything you need. We would love to come back!

Top guest favorite

A cozy living area features a comfortable gray sofa and a wooden side table with a decorative lamp. Large windows allow natural light to fill the space, while an air conditioning unit and TV are positioned nearby. A patterned area rug adds warmth to the hardwood floor.

Home in New Milford

5 out of 5 average rating, 8 reviews

Cozy cottage

JamesRating, 5 stars1 week ago

I have never had a bad Airbnb experience and I have even had a couple that were the best, better then what one could expect. This Airbnb is the Best in which I have ever stayed. One finds a place that matches its description and more. Outfitted for anything one would need when traveling, The place is extremely well maintained, everything works, great WIFI, and the hosts were instantaneously communicative, pro-active and responsive.

Guest favorite

A charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.

Cabin in Fishkill

4.96 out of 5 average rating, 106 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

AvrahamRating, 5 stars1 week ago

The cabin was exactly as listed and MORE! The nature and privacy you have will make you feel as though you've been transported to a different universe. Paul was an excellent host, providing clear instructions and recommendations, as well as proactively checking in to make sure the stay was going well! 10/10 recommend!!

Top guest favorite

Home in Poughquag

5 out of 5 average rating, 11 reviews

3 Bedroom Estate on Magical Hudson Valley Vineyard

LesRating, 5 stars6 months ago

This was a magical experience for our family. We immediately felt so comfortable in this beautiful top of the line home. No expense was spared when this home was built. We spent Thanksgiving here and were able to replicate all of our traditions. The kitchen made you want to prepare a feast, which we did. The amenities were abundant. The entire house was more than we could have imagined. Each bedroom had its own full bathrooms which were spotless and well appointed. The decor of the entire home had us in awe. The antiques and artifacts as well as the design in every square foot of the house was done so tastefully and obviously done with such love for the home. And the grounds! Stunning. Well maintained and so picturesque. From the wild horses to the babbling stream, the peaceful and serene environment was everything we were looking for. There is so much more that I can say about this home and host but have no space left. Thank you Kristin and hope you will have us back!

The interior features vaulted ceilings supported by wooden beams, with two ceiling fans and two glass pendant lights hanging from above. A large window allows natural light to fill the space, providing views of the surrounding trees.

Guesthouse in Brewster

5 out of 5 average rating, 4 reviews

Hidden Hope Cottage

NicholasRating, 5 stars4 months ago

Shannon’s place was great! It was very clean and all the necessities were provided. Also, the bed was super comfy! And Shannon was super responsive to any questions. Thanks for the wonderful stay.

Guest favorite

A modern kitchen is featured with sleek gray cabinets and stainless steel appliances. A dining table with four folding chairs is positioned centrally. Natural light enters through a large window, highlighting the light-colored tile flooring and the functional layout.

Guesthouse in Wappingers Falls

5 out of 5 average rating, 5 reviews

Spacious Studio Apartment

VeronicaRating, 5 stars2 months ago

It was a nice place very cozy. I felt just at home definitely recommend this place. Thank you again I loved it!!

The kitchen features a large window that allows natural light to fill the space, highlighting the farmhouse sink and vintage faucet. An AGA stove is prominently placed, alongside a countertop with various kitchenware. Light-colored cabinets and wood accents create a welcoming environment.

Home in Pawling

5 out of 5 average rating, 4 reviews

Quaker Hill Cottage

LindsayRating, 5 stars1 month ago

Quaker Hill Cottage was the perfect getaway from the city. From the moment we arrived, we felt completely at peace. The welcome basket was such a sweet and thoughtful touch. The bed was unbelievably comfortable. It was the first time in forever that I got a great night’s sleep. We cooked dinner and enjoyed drinks by the fire. Every little detail was wonderful. The shower was luxurious. In the morning we had breakfast outside on the terrace. Can’t wait to come back!

Guest favorite

An outdoor space features a circular stone patio with a central fire pit surrounded by several Adirondack chairs. Soft lighting is created by string lights overhead, and trees provide a natural backdrop, enhancing the serene atmosphere. Stacked logs are visible in the background.

Apartment in Holmes

5 out of 5 average rating, 14 reviews

Top Side

AnamariaRating, 5 stars3 months ago

Regan is the hostess with the mostess ! I would definitely visit again 😊

Show all

Vacation rentals in Whaley Lake

Top-rated vacation rentals in Whaley Lake

Vacation rentals for every style

Popular amenities for Whaley Lake vacation rentals

Other great vacation rentals in Whaley Lake

Destinations to explore