Holiday rentals in Port Chester

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Top-rated holiday rentals in Port Chester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Greenwood Lake

4.94 out of 5 average rating, 86 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Guest favourite

Home in Monroe

4.93 out of 5 average rating, 30 reviews

Rustic Blues Cottage Retreat

Kick back and relax in this calm, stylish space with an escape to the picturesque Hudson Valley for a Retreat like no other! Immerse yourself in the vibrant colors of the season, surrounded by the region's most breathtaking foliage. Our curated getaway combines adventure, relaxation, and festive fun. *PULL OUT COUCH in living room* Nearby: Woodbury Commons Premium Outlets Flagship Cinemas Legoland Renaissance Faire Pure Terror Scream Park Warwick Wineries Pumpkin Picking Apple Picking Hiking

Superhost

Guest house in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Superhost

Home in West Haven

4.79 out of 5 average rating, 43 reviews

Beachside Retreat

***Brand new to Airbnb, the Beachside Retreat is perfect for a quick getaway or a longer short term stay. Gorgeously renovated home has 4 spacious bedrooms, living room & dining room large enough to entertain and kitchen perfect for making those home-away-from-home meals. Across the street from the beach, wake up to stunning sunrises with your morning coffee or relax on the wrap around porch and watch the sunset. With walking trails, restaurants and shops close by you never have to go far.

Top guest favourite

Home in Ocean Beach

5 out of 5 average rating, 43 reviews

Sunny Spacious Pet Friendly Steps from the Beach

This ideally located four-bedroom home is the perfect spot for your family's vacation. The home features a spacious deck, central air conditioning, WiFi, 4 Smart TV's, a Sonos sound system and YouTube TV. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. There are 2 full bathrooms as well as an outdoor shower. Fully equipped including beach chairs, towels, 5 bikes, 2 wagons and beach toys for the kids. Sleeps 10.

Guest favourite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 338 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #33593

Guest favourite

Home in Milford

5 out of 5 average rating, 5 reviews

Seaside Paradise

Welcome to our beach house in Milford! This getaway is just a short walk from the beach, making it the perfect vacation spot for families or groups of friends. Whether you're looking to soak up the sun on the sandy shores, explore the charming town of Milford, or simply relax in a comfortable beach house, our rental is the perfect choice. We can't wait to host you and make your beach vacation unforgettable. Book now and start counting down the days until your beachside getaway!

Top guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 29 reviews

Greenwood Lake’s Iconic Lakefront “Icehouse”

Need a respite from the hustle and bustle of everyday life? This 4 Bedroom, 4 Bath home is located directly on the lake. Two floors of open living space with magnificent views of the lake and mountains. Families and couples can enjoy games indoors and out - with an expansive property and a chimenea fire pit and BBQ. A quick walk to Cove Castle Restaurant. 30 min drive to Legoland 20 min drive to wineries and breweries 15-20 min drive to NY Renaissance Faire PERMIT # 33387

Top guest favourite

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, 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!

Guest favourite

Home in Greenwood Lake

4.96 out of 5 average rating, 53 reviews

Water's Edge Lakefront Home

Enjoy this spectacular spot on the lake with stunning views and waterfront access. Close to NYC is a picturesque lake with water sports-swimming, boating etc! Short drive to wineries, breweries, golf courses, restaurants, local beach, weekend concerts on the beach, marinas, boat rentals, boat tours & nearby shopping. Nearby Warwick outdoor drive in and Bellvale creamery. Come and make special memories that will last a lifetime! STR Permit # 21 7853

Guest favourite

Home in Milford

4.91 out of 5 average rating, 57 reviews

Modern Beach Getaway

This 4 bedroom, 3 bathroom vacation rental in Milford, CT, boasts beautiful hardwood floors, high ceilings, and an open-concept living area perfect for entertaining guests. Each bedroom is tastefully decorated, and the fenced-in private yard features a deck and firepit area. The rental is located across the street from a private beach and is a short drive from local shops and restaurants, making it the ideal spot for a summer getaway.

Superhost

Flat in Greenwood Lake

5 out of 5 average rating, 3 reviews

Charming Two-Bedroom Getaway!

Discover the charm of our cozy 2-bedroom Airbnb, nestled in a serene neighborhood. Our inviting apartment offers the perfect blend of comfort, style, and convenience to many local attractions, dining, and shopping. You'll be close enough to the action yet tucked away in a peaceful area that allows you to relax and unwind.