Vacation rentals with outdoor seating in Fairfield

4.97 out of 5 average rating, 147 reviews

A modern kitchen features white cabinetry and a marble-like backsplash. Stainless steel appliances are present, alongside a spacious island with seating. Natural light fills the room through large windows, illuminating the light wood flooring that flows into a living area in the background.

Home in East Haven

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

4.85 out of 5 average rating, 144 reviews

The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.

Home in Ossining

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

5 out of 5 average rating, 7 reviews

A travel trailer is positioned on a grassy area, flanked by trees. Two entrance doors are visible, along with a picnic table set on a green mat. The exterior features a light color with subtle design elements, adding to its natural surroundings.

Camper/RV in Cold Spring

Couples One Night Hilltop Retreat AMAZING NATURE

Enjoy the lovely setting of this romantic spot in nature. Premier Hilltop RV in Cold Spring 1 BR w/queen, 1 pullout, 1 small single. Ideal for a couple, +1, or small family. On environmentally conscious farm w/ solar energy, fresh well water. Beautiful Scenic property w/ rolling hills, trails, rock scramble, small pond and stream. Near historic Cold Spring and Beacon, the Hudson River, kayaking, antiquing, quaint shops, dining, many hiking trails Breakneck Ridge, Clarence Fahnestock State Park.

5 out of 5 average rating, 3 reviews

A modern kitchen area features sleek cabinetry and stainless steel appliances. An island with a sink and seating separates the kitchen from the living space. Large windows allow natural light to fill the room, while a staircase is visible in the background.

Camper/RV in Fishkill

Luxury Get-A-Way Beacon/Fishkill

Come Stay @ This ALL NEW Glamper & Enjoy All That Beacon Has To Offer ! From Hiking, To All The Shops & Restaurants On Both Main Street Beacon & Fishkill. 10 Min Ride to Train Station, 5 Min Drive to Either Beacon Or Fishkills Main Street & 10 mins To Hiking You Are Never Too Far From Any Amenities But Away from Noise & Distractions. Outdoor Fireplace & Seating(Summertime)Electric Fireplaces Full BRAND NEW KITCHEN AND BATHROOM. Sleeps Up To 9 & is the PERFECT Place To Enjoy Each Others Company

5 out of 5 average rating, 10 reviews

A charming two-story home is showcased with a bright red front door and an American flag displayed. White siding complements the green landscape, while white adirondack chairs are positioned on the front lawn. Lush trees frame the property amidst a clear blue sky.

Home in Roxbury

Zoom In Map To 5*Roxbury "Painter Hill" PoshPadsCT

PoshPadsCT - Private 4-5-Bedroom hilltop retreat on a serene brook - a perfect getaway. New Hot Tub, Terrace, Trampoline. Located on a 3 acre property near historic estates, Maple Bank farm stand and Toplands Farm and just 1.5 hours from NYC. The house features beautiful fields, views, a large terrace with a gas grill, a firepit. Nearby hiking trails & Washington restaurants, shopping, distilleries, vineyards, breweries, and more! Ski Mohawk Mountain or Swim Lake Waramaug State Beach.

5 out of 5 average rating, 103 reviews

A serene lake is framed by a densely forested hillside, reflecting vibrant autumn colors in the calm water. The sky reveals soft clouds and a bright blue backdrop. A canoe is positioned at the edge of the dock, inviting exploration of the tranquil surroundings.

Cottage in South Salem

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

5 out of 5 average rating, 16 reviews

A spacious living area features a comfortable dark sofa complemented by patterned armchairs. Natural light enters through large windows adorned with sheer curtains, illuminating the neutral walls. A small coffee table and decorative elements add to the inviting setup.

Guesthouse in Bethel

Tranquil getaway cottage in charming neighborhood

Escape the city bustle and unwind in the tranquility of The Red Cedar Cottage nestled between Bethel and Newtown, just a short drive from Danbury, CT. Tucked away in a peaceful neighborhood, this fully renovated cottage offers a serene getaway for couples seeking relaxation. Unwind in style on a high-end king-sized mattress in a whimsically curated space designed to rejuvenate your senses. Discover the Red Cedar Cottage and immerse yourself in a tranquil escape from the ordinary.

5 out of 5 average rating, 102 reviews

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

Home in Milford

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

5 out of 5 average rating, 16 reviews

A glamping tent is nestled among trees, featuring a warm brown exterior. A wooden deck is visible, complemented by two lounging chairs positioned nearby. A circular fire pit made of bricks is located in front of the tent, surrounded by lush greenery.

Tent in Southbury

Romantic Botanical Glamping

A spiritual respite for relaxation and mental wellbeing. The perfect relaxing Romantic Botanical Glamping Spiritual Garden Retreat Getaway, off the beaten track but close to civilization with a rustic romantic flair. Pool, gardens, seasonal vegetables & fruit & Fall Colors. Local activities within minutes. Recline by the pool or gardens, or at the plush upscale movie theater in town. Antique trail, wine trail, breweries and distilleries. 24+ hiking areas.

5 out of 5 average rating, 11 reviews

A view of the Peconic River is depicted from a wooden deck, featuring a small round table and two woven chairs. The water reflects clear blue skies, with boats visible in the distance and trees lining the shore.

Houseboat in North Fork

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

4.98 out of 5 average rating, 60 reviews

A spacious camper is positioned amongst trees on a grassy area. A shaded picnic table sits nearby, and a fire pit surrounded by seating is visible on the lawn. Natural light filters through the surrounding foliage, creating a serene outdoor setting.

Camper/RV in Cold Spring

Country Getaway On Your Own Grassy Field

30 foot toy box camper 2 bedroom can sleep up to 7. On environmentally conscious farm operating on solar energy, and fresh delicious well water. Beautiful Scenic Cold Spring property w/ rolling hills, walking trail, rock scrambles, small ponds and a stream. Near historic Cold Spring and Beacon attractions, the Hudson River, antiquing, quaint shops, dining, many hiking trails - Breakneck Ridge, State Park w/ hiking and boating rental.