Holiday rentals in Orange

Renovated Apartment in a Historic Farmhouse Estate

Take-in fresh air and tranquil views from the 2nd floor deck of a 1-acre property with an adjacent apple orchard. Rustic decor mixes with industrial flair to create an inspiring interior that offers country comforts along with modern amenities. Enjoy hardwood floors, Queen memory foam mattresses, high ceilings, keypad door lock (no keys needed), fast Wifi, central air conditioning, & a private deck. We can't wait to host you! This is a multi-unit property, so we do not allow parties or events.

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

The Pond Mill Retreat w/ 2 Bdrms & Pool

Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

2 Bedroom with sweeping views of Long Island Sound

Entire 1st floor apartment with private entrance. A spacious layout with spectacular views of Long Island Sound from your private deck. Convenient location; minutes to downtown Milford, train station, beaches, restaurants, and shopping. 15 minutes to Yale and famous New Haven landmarks. Walking distance to local restaurants, beaches, and an ocean-side playground. Public Beach: 7 minute walk - 0.4 mi Restaurants: 6 minute walk - 0.3 mi Playground: 2 minute walk - 250' *NO SMOKING*

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

Downtown 2br-patio & walk 2 shps

Welcome to “Sails Call!” This 2BR/1BA is situated in the heart of Milford with views of the harbor. Just steps from restaurants, pickleball/tennis courts, shops, harbor and the train. Both bedrooms include AC window units & the kitchen is ready for you to cook a simple meal, or enjoy takeout. Coffee or cocktails on the private patio and park right on-site. Ideal for weekend getaways, business trips, or quick NYC escapes. Family friendly! Walk everywhere—ditch the car and explore.

Luxe cozy 2br/1ba Milford bungalow-walk to beach!

Beautifully updated bungalow 3 minute walk to beach. Features two decks for views & enjoyment of Silver Sands State Park. Back deck has dining table & grill for dinners, drinks, birdwatching, stargazing. House has cedar outdoor shower, two double kayaks, stand up paddle board, paddles, beach chairs/towels, umbrellas, cooler, wagon. Spacious living room has tons of natural light. Bedrooms are cozy each with a full bed; primary opens to back deck. 5 min drive to downtown Milford.

Westshore Luxury

Relax in the cozy living spaces, unwind in the bonus room, or take a peaceful stroll along the sandy beach just steps from your door. Enjoy breathtaking sunrises and sunsets over the water, fall asleep to the soothing sound of waves, or explore the scenic shoreline by bike. Whether you’re visiting for a quiet weekend escape or a longer stay, this charming beach home offers the perfect balance of comfort and tranquility. Quiet home for rest and relaxation — no parties or events.

Bohemian Beach Oasis- Private Beach

Designer beach house 120 steps to private beach on Merwin Avenue! Embrace the Bohemian life & escape w/ friends & family. Enjoy the spacious kitchen w/ granite counters & patio access. Bedrooms include a spectacular master suite offering a spa bathroom & 2 more bright rooms upstairs. The third-floor bonus room leads out to a rooftop deck w/ water views! Charming Tiki hut & BBQ for entertaining. Please reach out and schedule your special stay at the Bohemian Beach Oasis.

Oceanfront Beach House w/ Private Hot Tub

Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

4BR Beach Home | Walk to 3 Beaches | Sleeps 10

Wake up and walk to the beach in 3 minutes. This 4-bedroom Woodmont home sleeps 10 and is your perfect coastal escape. Three beaches within walking distance — Burwell (500 ft), Anchor (0.4 mi), and Woodmont (0.6 mi). Spend your days in the sun, then fire up the gas grill, relax on the deck, or play lawn games in the private backyard. Take a day trip into NYC. New Haven's famous pizza is 15 min away. Perfect for families and friend groups!