Pawling Holiday Rentals from €157: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Pawling has to offer?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond : This holiday home rental outside of Pawling is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

Check Pawling holiday rental availability

Holiday Rentals in Pawling

"It was a perfect setting for old friends to gather together. The house was very well equipped with everything in terms of platters for our spread, enough bathrooms and bedrooms, comfy seating and best of all windows looking out to their beautiful views. Horse farms and nice nature walks around the property and close to the cute town of Pawling. Definitely a must stay place."

"This house does have a lovely view that allowed us to take in the changing leaves off the reflection of the lake. The house is smaller than it appears in the photos and not quite as comfortable to just hang out, at least inside.The couch fits three, but there aren't other chairs in the living area. There are great little outside areas though. Communication with Katherine was great. Previous tenants had broken the washer which was a drag and due to weather (drought conditions) we couldn't use...

"Our group of 2 couples enjoyed our week in the Hudson Valley area. We all commented on the excellent beds and pillows, the view of the lake from the house and the quiet of the neighborhood. Would stay here again."

"Perfectly adorable house that was ideal for our brief getaway. I wish we had been able to use the kayak/canoe but time was tight. The only issue was the driveway which had me holding my breath a bit but luckily we were careful and managed without incident."

"I loved the location surrounded by mostly woods and the quiet atmosphere. The hosts are very nice and were very helpful. Everything I needed was inside. I may be back!"

"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"

"We wanted to spend a night in cold spring after a hike but couldn't find anything last minute in the area, so ended up booking this lovely property a little bit away. At first I was skeptical because of the drive (about 40-45 mins if I remember correctly). But I'm so glad we ended up doing this. Cold spring was just so busy and crowded, we couldn't even get lunch easily. The property is located right across a lake and is on a rather quite street. We reached the property around 5pm just in time...

includes taxes & fees

14 Nov - 15 Nov

"We had such a lovely weekend in this home. The house is so peaceful, overlooking a quiet lake surrounded by nature. We were very comfortable as the home was well-stocked and the check-in and check-out procedures were super easy. My nerdy husband was also very impressed by the very fast WiFi speed. Thank you so much for a wonderful stay!"

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"Everything was generally good. Station Inn is very nice and clean. The only thing I would say if you’re sensitive to noise, stay somewhere else. Train goes by a lot with the horn and the wall HVAC is loud. "

includes taxes & fees

12 Dec - 13 Dec

"If you need a place in Danbury or the surrounding area, this hotel is very near the Mall and is clean and well managed. "

includes taxes & fees

20 Nov - 21 Nov

Exterior Standard Room, 2 Double Beds, Non Smoking, Annex Building

"nothing to say"

includes taxes & fees

12 Dec - 13 Dec

Find out more about Pawling

Everything you need to know about Pawling holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pawling holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pawling holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pawling holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pawling. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pawling holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pawling holiday rentals we have selected for you start as low as €157 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pawling rentals

At Expedia, we put the best Pawling holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pawling rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pawling holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pawling. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Pawling properties

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

5/5 Excellent

"Will be back again. Nuce place "

A verified traveller stayed at Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Posted 2 days ago

Holiday Inn Express Poughkeepsie, an IHG Hotel

5/5 Excellent

"“I recently stayed at the Holiday Inn and had an exceptional experience. From the moment I arrived, Kashiem at the front desk made me feel warmly welcomed. His professionalism, friendliness, and attention to detail were outstanding and truly enhanced my stay. Kashiem went above and beyond to ensure everything was perfect, and his dedication to guest satisfaction deserves a 5-star review. I highly recommend this location and look forward to my next visit. Thank you, Kashiem, and the entire Holiday Inn team, for a wonderful stay!"

A verified traveller stayed at Holiday Inn Express Poughkeepsie, an IHG Hotel

Posted 3 days ago

Frequently asked questions

Are there holiday rentals in Pawling?

Yes, there are holiday rentals close to the most popular sights in Pawling, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pawling has to offer?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This holiday home rental outside of Pawling is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Pawling?

Choose from 4 Expedia holiday rentals in Pawling for a memorable holiday.

What can I see and do in Pawling?

While exploring the area, visit family-friendly sights like SplashDown Beach, or get outside and enjoy nature at Squantz Pond State Park. Other places in town to visit include John Kane House and Akin Free Library.

What are holiday rentals like in Pawling?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pawling. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips or small group gatherings.

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Holiday Rentals in Pawling

Check Pawling holiday rental availability

Holiday Rentals in Pawling

Stunning Pawling Retreat w/ Ponds & Waterfall

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock

Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!

Spectacular Short Term Vacation Rental in Kent

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Serenity Awaits at this Cozy Lakeside Bungalow

Cabin in the heart of the Hudson Valley, Cabin 4

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

The Long View of Candlewood Lake

Idillic summer getaway in Litchfield Hills, CT.

Cozy Cottage Getaway, Grill, Walk to Lake

Candlewood Lake Retreat with year round views

Stay 3 Nights or Longer Until January 31 and Get 15% Off

Entertainers Dream, Candlewood Lake, Hot Tub,Disco,Theatre,Music studio..more!

The Scenic Mansion With Breathtaking View

Other types of properties in Pawling you may be interested in

Station Inn Pawling

Ethan Allen Hotel

Quality Inn Poughkeepsie

Find out more about Pawling

Recent reviews of Pawling properties

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyatt Place Poughkeepsie / Hudson Valley

Hampton Inn & Suites Poughkeepsie

Courtyard by Marriott Poughkeepsie

Holiday Inn Express Poughkeepsie, an IHG Hotel

Wingate by Wyndham Fishkill

Hotel Zero Degrees Danbury

Maron Hotel And Suites

Best Western Fishkill Inn & Suites

Frequently asked questions