The Best Dog-Friendly Winter Getaways From NYC

Winter in New York City can feel like it lasts forever. After you’ve paced the length of your 900 square foot apartment for the millionth time and finally succumbed to cabin fever, you might find yourself browsing search engines in search of a flight to the nearest tropical destination.

But the truth is, hopping on a plane for a long weekend isn’t always the most practical solution. The good news is that there are plenty of dog-friendly getaway options closer to home, near New York City. Hop in a car and escape to a winter wonderland where you’ll recharge with more space, nature, and tons of relaxation. Get hygge with it!

We’ve compiled a list of charming winter weekend getaways from NYC that are all within a few hours’ drive of the city. Check it out.

Article Contents

1. Great Barrington, Massachusetts

Vogue magazine called Great Barrington “one of the most charming towns in the Berkshires,” and with good reason. This adorable town lies at the foot of Monument Mountain and Mount Everett, and has no shortage of winter hikes, skiing, and tubing right nearby.

The picturesque downtown is filled with top-notch restaurants and quaint stores selling everything from antiques, to books, to handmade pottery.

Bonus: check out one of the many legal cannabis dispensaries that the town has to offer.

Things to do in Great Barrington

Walk the trails up Monument Mountain
Stroll along the Housatonic River Walk
Check out Taft Farms
Buy old-fashioned sweets at Robin’s Candy Store
Have fun in the snow at Ski Butternut

Where to stay: The Briarcliff Motel

The Briarcliff Motel is a retro, pet-friendly roadside motel, located at the foot of Monument Mountain. They have 16 cozy guest rooms that come with Wi-Fi, plush-top mattresses with cotton-rich linens, and flat screen TVs. There’s also a free continental breakfast, a common room with board games and a pellet stove, and amazing views. Don’t miss their outdoor fire pit and the complimentary s’mores kit upon request.

Pet Policy: Great news: Briarcliff does not charge a pet fee! Their pet policy is as follows:

Be sure to clean up after your pet. Dogs are not permitted to dig or relieve themselves in the gardens. Solid waste MUST be removed and disposed of in the designated area.
Please be sure to take your pets out with enough time so that there are no accidents in the room. If your pet does have an accident, please report it to the Inn Keeper. Please note, if you need service for your room – we have not been servicing rooms during COVID. No room will be serviced with an uncontained animal.
Please do not groom/bathe your pets in the room and do not allow pets on the beds.
Pets must be on a leash at all times when you are walking outside as to be considerate of other guests. Well behaved pets CAN be left unattended in your room.
Disturbance or intimidation by your pet will not be tolerated. Any disturbances such as barking must be curtailed to ensure other guest satisfaction.
The Briarcliff Motel reserves the right to charge your account proportionate to the cost of such damages. Please be aware of your responsibility to make reimbursements on demand for any expenses incurred including compensation to other guests due to disturbances or inconveniences caused by your pet.
Please acknowledge that you will hold harmless Briarcliff, its owners and its operators from all liability and damage suffered as a result of your pet.

Location: 506 Stockbridge Road, Great Barrington, MA 01230

2. Stowe, Vermont

Called “The Ski Capital of the East,” Stowe is a charming small town in northern Vermont. This town is what winter scenes in movies are made of. It’s a classic New England town with a main street, lush surrounding mountains and peaks, and the perfect winter escape. In Stowe, the snow stretches out for miles and actually stays white, something any New Yorker would certainly appreciate!

Things to do in Stowe

Visit a craft brewery. Choose from The Alchemist (home of the famous Heady Topper), Idletyme Brewing and Stowe Cider.
Do a sleigh ride through the snowy wonderland with Gentle Giants.
Take in the views from the Trapp Family Lodge.
Take a snowshoe or snowmobile tour.
Stroll around the postcard-perfect downtown.

Where to stay: The Lodge at Spruce Peak

The Lodge at Spruce Peak is Stowe’s only ski-in, ski-out luxury resort. The Lodge features 300 guestrooms and suites, ranging from 450 sq. ft. to up to 1600 sq. ft. with multiple bedrooms.

Each stay comes with daily continental breakfast, epic views of the mountain with floor to ceiling windows, and free Wi-Fi. There’s an outdoor heated pool, roaring fires, and all types of winter activities offered, from cross country skiing, to ice skating, snowshoe hikes, and more.

Bonus: they even offer dog sledding! A team of sled dogs will take you on an unforgettable tour of the snowy woods and icy lakes surrounding Stowe. You’ll have plenty of time to meet the team and sip on complimentary hot chocolate or tea.

Pet Policy: There is a non-refundable dog fee of $125 per-stay, to be added when you book your room. This fee includes a welcome amenity of a dog-bed and chew toy at check in.

Not all guestrooms can accommodate travelers with dogs. Please call our reservations department directly for assistance in booking a dog-friendly room.
Dogs may not be left alone in the guest room at any time. Please contact the Concierge prior to arrival if you need assistance in scheduling pet-sitting services.
In the event that The Lodge at Spruce Peak incurs any loss of business or compensation is required for another guest due to noise complaints, those charges will be billed accordingly to your guest account.
All dogs must be on a leash at all times on the hotel premises.
Dogs are not permitted in the hotel restaurants, near the pool or pool deck, or other interior-public areas with the exception of arriving and departing through the main or upper lobbies.
Please clean up after your dog. Biodegradable waste bags are provided for you at Guest Reception.
If additional cleaning is needed for bedding, carpeting, or furniture, or if any damages are incurred due to your dog, all related charges will be billed to your credit card on file at the Front Desk.
Daily housekeeping service is not currently offered. Please be aware of your dog when requesting service. Daily service is provided between 8:30a-4:30p and turn-down service is provided between 5:30p-9:00p. Please contact Guest Reception to schedule a time for daily cleaning or turn-down that is convenient for you and your dog.
We cannot accept guests with cats. We apologize for the inconvenience.
The Lodge at Spruce Peak reserves the right to deny acceptance of any “dog guest” particularly in unfortunate situations where the dog becomes “unwelcome” due to aggressive behavior or disturbing other guests.
The Penthouses and luxury Residences cannot accommodate travelers with dogs.

Location: 7412 Mountain Road, Stowe, VT 05672

3. Phoenicia, New York

Phoenicia is a popular getaway for New Yorkers during the summer, but don’t sleep on this Catskills town in the winter. It’s packed with small-town charm during the colder months too, with plenty of hiking trails, sleepy cafés, and quaint little shops. And with it’s close proximity to the city, it makes for an easy escape for a weekend away. It’s the perfect place to relax and recharge!

Things to do in Phoenicia

Grab some grub at the famous Phoenicia Diner.
Ski at Hunter Mountain, home to a 1,600 foot vertical drop!
Snowshoe along Wittenberg Trail.
Hike up Overlook Mountain and don’t miss the ruins of an old hotel.
Grab a beer and a bite at Woodstock Brewing.

Where to stay: The Graham & Co. Hotel

The Graham & Co. Hotel is a 20-room boutique hotel located at the base of Hunter Mountain. It’s just a couple blocks from Phoenicia’s downtown, making it an easy jumping off point when exploring what the small town has to offer. It has a rustic feel to it (unfinished wood, beamed ceilings, antique touches and earth tones), so don’t forget your flannel.

Pet Policy: They offer a limited number of dog-friendly rooms, and dogs are permitted with permission ($25 fee per night). Call ahead for availability.

Location: 80 Route 214 Phoenicia, New York

4. Watch Hill, Rhode Island

When you think of winter getaway, Watch Hill might not be the first place that comes to mind. The affluent coastal village, located at the most southwestern point in all of Rhode Island, juts into the Block Island Sound and is surrounded by the Atlantic. While it’s a paradise in the summer, it’s equally as charming in winter months.

Spend an idyllic winter holiday in this hideaway town surrounded by snow capped trees and frigid blue waters. Watch Hill is the perfect backdrop for a cozy, refreshing winter romp.

Bonus: if you’re lucky, you’ll snag a peek of Watch Hill’s most famous resident – Taylor Swift! She owns a home here.

Things to do in Watch Hill

Birdwatch and hike at Napatree Point.
Ride the the oldest working carousel in the country, the Flying Horse Carousel.
Indulge in ice cream at the St. Clair Annex.
Visit The Candy Box, a delightful old-school candy shop.
Enjoy the views at the Watch Hill Lighthouse.
View the bronze statue of Indian chief Ninigret, the “Guardian of Watch Hill.”

Where to stay: Ocean House

Ocean House is a sprawling estate located on the waterfront, dating back to 1868. This legendary New England resort is well known for their hospitality, stellar service, and world-class amenities, including a spa overlooking the ocean, a restaurant, and access to a private beach. The lobby alone has a piano, architectural columns, and a beautiful fireplace, and rooms come with spectacular views and plush beds – some even have soaking tubs!

Pet Policy: Ocean House accepts dogs under 35 lbs. They apply a one-time cleaning fee of $195 to your bill. Pets are not permitted in their Signature Suites or Cottages.

Location: 1 Bluff Avenue, Watch Hill, RI 02891

5. Manchester, Vermont

There’s a reason people flock to this small southern Vermont town during all four seasons. Manchester is the quintessential New England town, with white church steeples, breweries serving up cold craft beer, and rolling hills to ski or hike.

In the winter, it’s a snow-covered ski town where you’ll find beautiful wintery scenery around every corner. There are sleigh rides, dog sledding, and ice skating throughout town, and of course, cocoa by the fire. You won’t be sure if you’re stuck in an episode of Gilmore Girls or if you’re actually living real life.

Things to do in Manchester

Browse the aisles at the famous Northshire Bookstore.
Grab a latte at the charming Spiral Press Café.
Ski the slopes at Bromley Mountain.
Eat a hearty breakfast at Bob’s Diner.
Get a sleigh ride at Mountain View Ranch.
Check out Hildene House, the former estate of President Lincoln’s son, Todd.

Where to stay: The Equinox Golf Resort & Spa

Much like the town itself, The Equinox is steeped in local history. Since 1769 they’ve hosted presidents and American Revolutionaries, and today, they’ve outfitted the resort with 195 guest rooms and suites, ranging from Vermont rustic to modern luxury. They have five dining experiences to offer, a spa and fitness center, a heated indoor pool, and a Falcon Deck fire pit with views of Mt. Equinox.

The Equinox is also home to Cooper, a Golden Retriever who serves as their Chief Happiness Officer. Cooper is on hand to greet guests, provide snuggles, play fetch, and even to accompany guests on hikes. You can follow him on Instagram here.

Besides that, The Equinox offers a variety of wintery outdoor adventures to make your winter escape even richer. In addition to skiing, there are sleigh rides, winter hikes, cross country skiing, snowmobiling, sleighing, and even dog sleds.

There’s also an outdoor skating rink, tubing, snowshoeing, and s’mores kits by the fire pit upon request. There’s no shortage of activities, with 914 acres of mountain trails right through The Equinox’s backyard.

Pet Policy: Pets are always welcome at The Equinox. Weight limit of a dog shall be 80 lbs or less. Dogs over 80 lbs may be allowed at the hotel’s discretion. They charge a one-time non-refundable pet deposit of $130 for one dog and $50 for an additional dog (two dog maximum). In accordance with the local health codes, dogs are not allowed in the restaurants or the pool. Call The Equinox in advance to inform them if you are bringing your pet.

Location: 3567 Main St. Manchester Village, VT 05254

6. Hunter, New York

Hunter, NY is a quaint little town that sits atop the high peaks of the Great Northern Catskill Mountains. Best known as a world-class skiing destination, Hunter has plenty to offer during the winter months. The rocky, mountainous terrain is home to stunning scenery that’s perfect for nature lovers, and their selection of cozy accommodations provide loads of comfort.

Things to do in Hunter

Ski at the Hunter Mountain Resort.
Go horseback riding at Bear Creek Landing.
Sip on local wine and beer at the Hunter Mountain Brewery.
Go snow tubing at the Hunter Mountain Snow Tubing Park.
Go on a scenic skyride on the Kaatskill Flyer, the longest and highest skyride in the Catskills.

Where to stay: Scribner’s Lodge

Scribner’s Lodge is the perfect basecamp for your escape to the outdoors. The lodge features 38 guest rooms and suites, a locally-inspired restaurant, and over 20 acres of mountainside to explore.

The common areas have fireplaces and there’s an outdoor fire pit too (don’t forget to ask for a s’mores kit!). Don’t miss Old Man Scribner’s Garden, a beautiful garden that’s open year-round for guests to walk through – it’s where much of the restaurant’s produce is grown.

Bonus: be on the lookout for their Pupstater events! These special weekends happen multiple times a year, with special activities and perks designed specifically for humans and their dogs.

Pet Policy: Scribner’s welcomes well-behaved dogs into their Pupstater Program for a $50 nightly non-refundable fee for up to two dogs. Any additional dogs will incur an additional $50 nightly fee. All Pupstaters will receive toys and treats to take home as well as bowls to use while they are visiting Scribner’s.

Location: 13 Scribner Hollow Rd, Hunter, NY 12442

7. Stockbridge, Massachusetts

Yes, another Berkshires town made the list, but can you blame us? The allure of the Berkshires exists for a reason. Stockbridge is packed with endearing small-town ambiance, which attracts New Yorkers from all walks of life to soak up some New England charm.

The picturesque village is best known for its most famous resident, artist Norman Rockwell. Step back in time and take a stroll down Main Street, taking in the sites that inspired Rockwell.

Bonus: One of Norman Rockwell’s most well known paintings is of Main Street, Stockbridge, in magical wintertime! It took him eight years to complete.

Things to do in Stockbridge

Connect with nature at Goodrich Memorial Park – check out Ice Glen!
Go ice fishing at Stockbridge Bowl.
Hike up Monument Mountain.
Dine at one of the local cafes and restaurants on Main Street.
Visit the Norman Rockwell Museum.
Smell the flowers at the Berkshire Botanical Garden.

Where to stay: The Red Lion Inn

The Red Lion Inn is an iconic landmark that dates back to 1773. They’ve been offering food and lodging to guests since the colonial days! It’s such a popular Stockbridge staple that even people not staying at the Inn visit this historic location.

The Inn offers four unique lodging experiences, including the classic Main Inn, the modern country feel of Maple Glen, and the unique houses in the Village. There’s even a turn-of-the-century Firehouse. No two rooms or buildings are the same.

There are four dining options to choose from that include a wine list with over 400 selections. Don’t forget to try their famous Bloody Marry, or to sit on the front porch that’s stocked with rocking chairs.

The Red Lion Inn’s well known gift shop offers souvenirs and gifts, like Red Lion chowder mugs, gift boxes of jams, and stuffed red lions. There’s an outdoor, year-round heated pool and hot tub, so yes, you can go swimming, even in the winter.

Bonus: the Inn is featured in Norman Rockwell’s painting The New American LaFrance is Here.

Pet Policy: Well-trained and quiet pets are always welcome in selected first-floor guest rooms and suites. They are provided with a welcome treat upon arrival – just to make them feel at home. Please call to make a reservation.

A few policies to ensure your pet’s visit is as pleasant as possible.

Prior reservations are necessary and available on a limited basis. Please let us know ahead of time. There is a $40 fee per night.
Please keep your animal on a leash when outside your room. This is for your pet’s protection as well as in consideration of other guests and staff.
Please do not leave your pet unattended all day in your room. Pets must be secured in crates when left in the room. Housekeeping will not attempt to enter or clean your room if your pet is not secured in a crate. A limited number of crates are available from the front desk.
Pets are not allowed in public areas.
Please manage your pet’s barking or other noise in consideration of your neighbors.
Unattended pets that disturb others will be relocated at the owner’s expense.
Guests are responsible for any and all damage or injury caused by their pet and do not hold the Inn or its staff liable for injury to another guest or staff member.
Please ensure that your pet is considerate of our antiques and do not allow them on our furniture.

Location: 30 Main St, Stockbridge, MA 01262

8. Lake Placid, New York

Surrounded by the snowy High Peaks of the Adirondack Mountains, you won’t run out of things to do in winter at Lake Placid. Lake Placid comes alive in the winter. In fact, it was home to the Winter Olympics not once, but twice (in 1932 and 1980). It’s considered the best place on the East Coast for snow sports, making it the perfect winter getaway in Upstate New York.

Head here if you’re looking for some adventure in chilly temps or just a good time outdoors.

Things to do in Lake Placid

Check out the snow-covered rooftops on Main Street.
Visit Big Slide Brewery for craft beer and views of the Olympic Ski Jumps.
Take a thrilling dog sled ride across Mirror Lake with either Thunder Mountain Dog Sled Tours or Mike Arnold Dog Sled Rides.
Grab maple soft serve from Emma’s Lake Placid Creamery on Main Street.
Go skiing or snowboarding on Whiteface Mountain.
Go down the 30-foot high Lake Placid Toboggan Chute.
Treat yourself to a horse-drawn sleigh ride.
Rocket down the tracks at the Lake Placid Bobsled Experience.

Where to stay: The Lake Placid Lodge

The only hotel located directly on Lake Placid, the Lake Placid Lodge is a quintessential Adirondack property with large stone fireplaces, beds made out of tree branches, and stunning views of the lake. Dogs are allowed in the private, cozy cabins just a short walk from the main lodge and only steps from the water.

The snowy forest and the frozen lake can be explored on foot, skis or snowshoes, or enjoyed from the comfort and warmth of your cabin’s fireplace. There’s a well-stocked pub with games like billiards, backgammon, chess, and cards, as well as food and drink. Don’t forget to bring a book for the Lodge’s many deep armchairs and cozy fires.

Winter activities on site include snowshoeing, cross country-skiing, ice skating, and snow bonfires with s’mores.

Pet Policy: Lake Placid Lodge welcomes well-mannered dogs. Guests bringing dogs will be charged $75 per night, per dog; maximum of two dogs per room. Dogs are allowed only in our cabins; each cabin can accommodate up to two dogs. Room type and location restrictions may apply. Guests will be responsible for any property damage inadvertently caused by their dogs.

Dogs must be on a leash at all times if outside the cabin, and are not permitted inside the Main Lodge. Dogs left in a cabin unattended must be securely crated for the safety of the housekeeping staff. If your dog has a tendency to bark in your absence, they request that your dog not be left alone.

Location: 144 Lodge Way, Lake Placid, NY 12946

9. Kennebunkport, Maine

Is Kennebunkport the best winter town in Maine? Many seem to think so! This sleepy, coastal New England town is full of maritime-themed and natural scenery.

During the Christmas season, the entire town dresses up in sparkling lights, wreaths and buoys and puts on a holiday show. Festive trees are decorated with lights and lobsters, there’s caroling and fireworks, and even Santa arriving by lobster boat.

In late January and February, the town hosts Paint the Town Red, their annual Valentine celebration with pops of red and festive hearts, romantic packages, and a host of wintery events planned all over town.

Things to do in Kennebunkport

Ride a trolley through the woods at the Seashore Trolley Museum.
Marvel at the Christmas Prelude, a two-week celebration for the lighting of the tree in Dock Square.
Go candlelight caroling at the Franciscan Monastery.
Check out the fireworks every Friday night.
Cross country ski or snowshoe at nearby Wells Reserve at Laudholm Farm.
Go ice skating at Kennebunks Waterhouse Pavilion.
Drink craft beer at the Kennebunk Brewpub.
Enjoy a horse-drawn sleigh ride from the Rockin’ Horse Stables.
Take your dog for a walk on Gooch’s beach.
Shop at Scalawags, the local pet store.

Where to stay: Kennebunkport Captains Collection

Just steps away from Dock Square, the Kennebunkport Captains Collection, known as the KCC, is a modern collection of four historic Maine homes formerly owned by leading sea captains. The mansions of the Captains Collection – Nathaniel Lord Mansion, William Jefferds House, James Fairfield House, and Acton Patterson House – are among the oldest in Kennebunkport’s historic district. There are working fireplaces in (almost all) guest rooms, and each stay comes with a complimentary breakfast.

Pet Policy: We are happy to allow up to two 70 lb or less canine companions in a select number of pet-friendly rooms at William Jefferds House. The Jefferds Terrace King, Jefferds Studio Suite with private exterior entrance, and William Jefferds Suite are our designated pet-friendly guest rooms.

Pet fees include a $50 per dog, per night rate increase. Please call the property directly to inquire about booking a pet-friendly room. Additional dog policy details:

Please add a note in the “Notes” section at checkout letting us know the quantity, size, and name(s) of your dog(s).
While we love our pets, not all of our guests feel the same way. For this reason, pets are never permitted in interior public spaces—they are permitted only in our exterior common areas, and only while on leash.
Pets must never be left in guest rooms alone.
If applicable, dogs are never allowed in property pools, pool deck areas, or indoor restaurants.
If unregistered dogs are discovered in rooms, or if a pet causes stains or damage to a pet-friendly guest room, a charge of $250.00 will be added to the guest’s credit card on file.

Location: 6 Pleasant St, Kennebunkport, ME 04046

What’s your favorite place to escape to in the winter? Learn more about dog-friendly NYC here.

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The Best Dog-Friendly Winter Getaways From NYC