Pet-friendly holiday rentals in New Milford

4.96 out of 5 average rating, 191 reviews

A warm wooden interior is highlighted by a charming dining area featuring a small table set for two. Natural light streams through double doors, revealing scenic views outside. Soft curtains adorn the windows, and a small kitchenette is visible in the background.

Guest suite in Sherman

Cozy Scenic New England rural retreat hike & kayak

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian Trail & other great hiking. Family friendly beach on Lake nearby. Pets welcome. Inquire min stay requirements.

WalkabilityPetsBarbecue

5.0 out of 5 average rating, 151 reviews

A spacious studio apartment features large windows allowing natural light to fill the room. A comfortable king size bed is positioned alongside a cozy seating area with a sofa and coffee table. A textured area rug covers the hardwood floor, adding warmth to the space.

Apartment in Pawling

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.

WalkabilityPetsCleanliness

4.97 out of 5 average rating, 133 reviews

A serene river view is framed by tall trees, creating a natural canopy overhead. In the foreground, two Adirondack chairs are positioned on the grassy bank, inviting relaxation while overlooking the calm water surrounded by lush greenery.

Home in New Milford

Idyllic retreat on the water <1.5 hrs to NYC.

Private getaway on 3+ acres on the river with no visible neighbors, sit by the river or in the enclosed patio with view of the water, walk the trails in the area. Great for short escapes or longer discounted stays enjoy great restaurants, antiquing, swimming, hiking, and access to all New England has to offer. In spring, summer and fall lots of open air activities to be had. Fishing, boating, farmers markets and flea markets. In winter many nice walks to be had, skiing is not too far away.

Outdoor spacesPetsDecor

5.0 out of 5 average rating, 142 reviews

Apartment in Holmes

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

Outdoor spacesWalkabilityQuiet

4.98 out of 5 average rating, 103 reviews

A gravel driveway leads to a welcoming villa, surrounded by manicured lawns and lush trees. Stone pillars with decorative features frame the entrance, while vibrant flower beds add color to the landscape. A serene natural backdrop of trees provides a peaceful setting.

Cabin in Cornwall

Beautiful country house in Cornwall CT.

If you love being in touch with nature, this is a perfect and pleasant place to enjoy with family and friends and wake up to the sound of birds! and enjoy all the seasons of the year. And in winter you can escape 15 minutes to this area of Mohawk paradise and if you are a fishing lover, the House-tonic River is just 5 minutes away, 2 minutes to Kent Falls, 7 minutes to Kent where you can find restaurants and a grocery store! You can enjoy beautiful flower gardens from spring to fall.

WalkabilityPetsAmenities

4.9 out of 5 average rating, 238 reviews

A charming three-story farmhouse is surrounded by lush greenery, featuring a welcoming front porch with seating. The design includes a shingled exterior and a pathway leading to the entrance, all set against a backdrop of vibrant trees.

Home in Sharon

Charming and relaxing 4b farmhouse group getaway

We are thrilled to share our idyllic country home with you and hope you enjoy it as much as we do. Built in 1882, set on a hill with ample indoor and outdoor space (two kitchens!) overlooking the Housatonic River and the famous West Cornwall bridge, our fully stocked house is close to hiking, fishing, kayaking, skiing/snowboarding. Set in gorgeous Litchfield Hills near the Appalachian trail, wineries, breweries, farms, rivers and lakes, waterfalls, antiques, casual or fine dining

WalkabilityPetsBackyard

4.99 out of 5 average rating, 147 reviews

Home in Newtown

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

PetsOutdoor spacesKitchen

4.88 out of 5 average rating, 369 reviews

A stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.

Farm stay in Kent

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

WalkabilityOutdoor spacesWi-Fi

4.96 out of 5 average rating, 457 reviews

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

Outdoor spacesWalkabilityHiking

4.93 out of 5 average rating, 139 reviews

A spacious deck is furnished with several striped lounge chairs surrounding a central table. Soft glow lights are suspended overhead, illuminating the area. A panoramic view of the lake and vibrant sunset colors create a serene setting for relaxation and social gatherings.

Home in Brookfield

Sleeps 18 LAKE VIEWS! Perfect for large group!

*We only book to 25 or older PERFECT SPOT TO BRING YOUR BOAT! This home sleeps up to 18 people + is perfect for large groups, wedding parties or team retreats. You’ll love the sunset views, large living room and kitchen for entertaining and hanging out, pool table, dart board and large yard for games. There’s even a spot to bring your own boat or jet ski and room to park your trailer! IG stay_at_the_lake

Outdoor spacesPetsCondition

4.99 out of 5 average rating, 103 reviews

Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

Outdoor spacesPetsBathroom

Guesthouse in New Milford

A gravel area is framed by a rustic wooden fence and lush greenery. The parking space is bordered by low shrubs, and a glimpse of the neighboring cottages is visible in the background, surrounded by trees and a serene setting.

4.92 out of 5 average rating, 217 reviews

Charming Cottage w/Pastoral Views

Our charming and comfortable one bedroom apartment/cottage offers a dramatic 2-story window, a pastoral setting and a welcoming country atmosphere. Easy access to all of Litchfield County, incl the bucolic towns of Kent, Washington & New Milford.

Outdoor spacesWalkabilityGetting around

Popular amenities for New Milford pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 149 reviews

The exterior of a charming Dutch colonial house features a white facade framed by vibrant green trees and seasonal foliage. A white picket fence encloses the manicured lawn, while a walkway leads to the front porch that is accented by shutters and a welcoming entrance.

Home in Kent

Kent village home 2 hrs from NYC

WalkabilityPetsHiking

4.85 out of 5 average rating, 123 reviews

A light-filled living area features a white sectional sofa and natural decor. Shelves with decorative items and plants enhance the space. The open layout leads to a dining area visible in the background, with wooden furniture and a textured rug grounding the room.

Home in Bethel

Boho house near NYC

PetsWalkabilityAccuracy

4.97 out of 5 average rating, 110 reviews

The exterior view of the house is framed by overhanging tree branches with red leaves. A swing hangs from a nearby tree, and the stone fireplace is visible on the house's side. A spacious, grassy yard surrounds the home, creating an inviting setting.

Home in Kent

Cozy house w/ screened porch near Kent & falls

WalkabilityPetsHospitality

4.98 out of 5 average rating, 130 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

WalkabilityOutdoor spacesComfort

4.93 out of 5 average rating, 212 reviews

A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Outdoor spacesPetsAccuracy

4.81 out of 5 average rating, 457 reviews

A two-story blue house is framed by lush green trees and shrubs, creating a natural setting. A bright red door serves as an inviting focal point, while a stone path leads to the entrance, enhancing accessibility.

Home in Litchfield

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Outdoor spacesWalkabilityAccess

4.93 out of 5 average rating, 230 reviews

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

Lux Bungalow on the Lake

WalkabilityOutdoor spacesCheck-in

4.93 out of 5 average rating, 118 reviews

A blue-brick exterior is complemented by a landscaped yard featuring two lounge chairs with light blue cushions. A dining area with an umbrella sits adjacent to the building, while stone pathways lead to the entrance flanked by greenery.

Home in Warren

Litchfield County Getaway

Outdoor spacesWalkabilityCleanliness

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 224 reviews

A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.

Guest suite in Holmes

Huge eclectic space w/ private pool. 1.5hr to city

WalkabilityPetsValue

4.96 out of 5 average rating, 394 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

PetsWalkabilityShared spaces

4.83 out of 5 average rating, 118 reviews

The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.

Home in Litchfield

The Getaway-HOST & Co.

Outdoor spacesPetsIndoor spaces

4.99 out of 5 average rating, 328 reviews

The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.

Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

Outdoor spacesPetsLong stay

5.0 out of 5 average rating, 187 reviews

A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

PetsOutdoor spacesCheck-in

4.92 out of 5 average rating, 180 reviews

Home in Beacon

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

PetsOutdoor spacesLocation

4.96 out of 5 average rating, 143 reviews

A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.

Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

PetsOutdoor spacesTV

4.9 out of 5 average rating, 149 reviews

An outdoor pool area is surrounded by lush greenery, featuring a rectangular pool with sun loungers and umbrellas for shade. A covered pavilion offers seating for relaxation, while a gently sloping lawn adds to the serene atmosphere. The nearby house is visible in the background.

Home in Town of Milan

Private Estate w/Pool, Hot Tub+Sauna nr Rhinebeck

Outdoor spacesPetsHeating

Private, pet-friendly home rentals

4.93 out of 5 average rating, 225 reviews

Two dome homes are nestled among lush greenery, connected by a spacious wooden deck. Soft outdoor lighting highlights the natural landscape, while the architecture features large arched windows. A pathway leads through well-maintained garden beds, enhancing the tranquil setting.

Cabin in Cornwall

Vibrant, secluded dome home in Litchfield County!

PetsOutdoor spacesNearby

4.99 out of 5 average rating, 169 reviews

The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.

Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

WalkabilityPetsHiking

4.94 out of 5 average rating, 130 reviews

A view from the cozy bed showcases a window adorned with soft curtains. Outside, lush greenery and vibrant pink flowers are visible through the glass, enhancing the connection to nature.

Guest suite in Pawling

Cozy retreat just a short stroll from the village

WalkabilityOutdoor spacesAir conditioning

4.84 out of 5 average rating, 514 reviews

An A-frame structure is positioned among trees, showcasing wooden siding and large windows. An outdoor deck features seating for relaxation, while warm light emanates from within. The surrounding landscape hints at a peaceful and wooded environment, enhancing the retreat's tranquil atmosphere.

Cabin in Carmel Hamlet

The Treehouse Lovenest

PetsWalkabilityBathroom

4.87 out of 5 average rating, 133 reviews

An open-concept great room features floor-to-ceiling windows offering unobstructed views of the lake. Exposed wooden beams accentuate the ceiling, while a spacious dining table and comfortable seating area create a welcoming space. Natural light is complemented by modern pendant lighting throughout.

Cabin in Holmes

Charming Hudson Valley Lakefront Escape with Views

Outdoor spacesPetsBackyard

4.96 out of 5 average rating, 92 reviews

The cabin sits elevated on a stone foundation, surrounded by trees at night. Soft lighting highlights the porch and pathway, creating a warm ambiance. String lights adorn the balcony, and the house features large windows, showcasing a welcoming atmosphere.

Cabin in New Milford

Private Hilltop Cabin at Houndcliffe

Outdoor spacesPetsCheckout

4.97 out of 5 average rating, 31 reviews

The welcoming farmhouse is framed by lush green lawns, with a distinctive green metal roof. A spacious porch extends across the front, complemented by a fire pit area. A small shed is visible to the left, surrounded by trees against a clear blue sky.

Farm stay in New Milford

Mabels Hollow Farm in Litchfield County

PetsOutdoor spacesBeach