Vacation rentals with outdoor seating in Milford

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Milford

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Tent in Poughquag

4.85 out of 5 average rating, 13 reviews

Maybrook Farm "The Ridge"

Soaring view of Hudson Valley from tent on 100 Acre Farm - Direct Access to Empire Rail Trail - Fishing at our Pond! Walk to Appalachian Trail! Enjoy the stars at night and beauty of hills and valley from your canvas tent equipped with bed. Drive up or come by bike to private entrance to the farm from the Empire Rail Trail with a locked gate. The pond has a dock, there is a seasonal babbling brook, walking trails, wildlife. Fire pit, picnic table, outhouse bathroom. Rustic, simple, beautiful!

Superhost

Home in Roxbury

5 out of 5 average rating, 22 reviews

Zoom Map 5* Town Roxbury! "Tophet Pool" PoshPadsCT

PoshPadsCT - 1-BR Large Open Pool House with Rec Room/Office/Sleeper Queen Sofa. Luxury Down Feather Beds, Comforters, Pillows, Frette Pressed Cotton Sheets, towels, Bathrobes. Roxbury and Washington are the best country escapes under 2 hours to NYC with the best homes, restaurants and activities. It is the country escape of choice to actors, writers, artists, Wall Street execs and more. A rural farm area of the best homes and estates in historic Litchfield County. Best country destination!

Top guest favourite

Chalet in Poughquag

4.97 out of 5 average rating, 74 reviews

The Lookout

Massive 4,000 sq foot chalet on more than seven acres. Only 90 minutes from NYC, with incredible mountain views and stunning sunsets. Floor-to-ceiling stone fireplace, outdoor firepit, 8 person hot tub, and gas grill for use. Private hiking trail on property. Close proximity to all of Hudson Valley's best golf courses, breweries, wineries, hiking trails, parks, and ski resorts. Easy drive to historic Beacon, Cold Spring, Rhinebeck, Pawling, and New Paltz, and only minutes away from Metro North.

Guest favourite

Home in East Haven

4.97 out of 5 average rating, 149 reviews

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.

Top guest favourite

Cottage in South Salem

5 out of 5 average rating, 103 reviews

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.

Top guest favourite

Guesthouse in Bethel

5 out of 5 average rating, 16 reviews

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.

Top guest favourite

Home in Milford

5 out of 5 average rating, 102 reviews

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!

Top guest favourite

Tent in Southbury

5 out of 5 average rating, 16 reviews

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.

Top guest favourite

Villa in Westville

4.98 out of 5 average rating, 130 reviews

Group Getaway near Yale | Hot Tub & Cozy vibes

Enjoy a bright, spacious home just minutes from Yale and downtown New Haven. Perfect for families, friends, or coworkers looking to relax, connect, and recharge. Features a fully equipped kitchen, 5 comfy bedrooms, fast Wi-Fi, a private backyard with a hot tub, and a peaceful vibe. Walk to parks, cafes, and local spots. Ideal for mindful gatherings, work trips, or celebrating special moments together.

Guest favourite

Dome in Newtown

4.95 out of 5 average rating, 172 reviews

Dome w/cooling fans on solo campsite.

NOTE: If this space is booked for the dates you chose, we have a similar listing. Send an inquiry and we will respond with the link. Unique/solo campsite, adjacent to 150 acres of open space w/4+ miles of marked trails. Secluded, peaceful, and quiet..AND only 1.5 miles to major shops. Enjoy time hiking or relaxing by the campfire. Perfect couple's weekend getaway to sleep under the stars!

Top guest favourite

Home in Woodmont

4.92 out of 5 average rating, 259 reviews

Bright and Breezy Cottage by the Sea

Bright and breezy beach cottage, 500 ft walk to a private beach on the scenic Long Island Sound! Newly renovated, 100 year old, cozy home in a friendly, quiet residential neighborhood. Relax on the deck, in the hammock or take a luxurious shower outside under the stars. A partially stocked new kitchen is at your disposal along with a washer dryer. House is Solar powered.

Guest favourite

Home in North Fork

4.93 out of 5 average rating, 85 reviews

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.