Holiday rentals with a pool in Essex County

4-Bed Home w/Pool + Walking Trails + Dead End St.

This dog-friendly home on a dead-end street features a large in-ground pool, exposed beams, walking trails that are located next to the home. HIGHLIGHTS: • Large private fenced-in pool • 1st Floor Ensuite (Half Bath) Primary Bedroom • 3 Bedrooms on the First Floor • Dead-end Street • Dog-Friendly (up to 2 dogs) • Next to Steer Swamp Nature/Walking Trails • Stainless Steel Kitchen • Exposed Beams • Off-Street Parking • 0.7 Miles to Old Town Marblehead • 0.8 Miles to Fort Sewall • 0.2 Redd's Pond

Value · Location · Hospitality

Sunset Waterfront Retreat | Private Beach, Pool &

Waterfront retreat with private beach access, panoramic marsh views, and unforgettable sunsets. Designed for families and groups looking to relax, reconnect, and enjoy the best of Plum Island living. Enjoy the private pool (open seasonally), expansive outdoor living spaces, firepit lounge, and peaceful wildlife views directly from the property. Spend your days walking the island, to local beaches and restaurants, or simply unwinding by the water. Inside, the home features a modern kitchen, was

Value · Location · Heating

Private Suite• Pool • Sleeps 4 • Boston • Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

Value · Family · View

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Value · Family · Air conditioning

Cozy, with Lots of Space

Garden level suite in a quiet single family home. Walk to commuter rail, downtown, restaurants & grocery stores. Ideal for extended stay professional or grad student seeking a private and quiet space. Fully furnished - a separate bedroom (king bed), living/dining, bathroom & kitchenette (sink, small fridge, microwave - **NO STOVE**). Cooking is not allowed. Includes 2 TVs w/ streaming, wi fi, laundry, pool & monthly cleaning service. Off street parking. No large gatherings or parties allowed.

Location · Value · Parking

Heated Pool Firepit Huge Screen Porch King bed

Beautifully renovated New England home with classic charm and modern comfort. Enjoy spacious living room, family room with gas fireplace, and bedrooms with vaulted ceilings. Full kitchen, heated pool (seasonal), large screened porch, outside dining, fire pit, gas grill, and outdoor seating. Heat/AC for year-round comfort. Peaceful setting amid woodlands. Prime location: 15 minutes to Wingaersheek Beach or Crane Beach, 1.5 miles to Conomo Point. We love calling this home, and hope you will too!

Location · Family · Beach

Theatre | Arcade | Pool w. Free 3 Car Parking

Experience The Chelsea Retreat, your private escape with free parking for up to 3 cars and an average 15 minute drive to Boston’s top attractions! Enjoy a cinematic night with a 150” 4K theatre and immersive surround sound, challenge friends in the arcade with foosball, pinball, and classic arcade games, or unwind beneath the gazebo before floating the day away in the pool. Shoot hoops, fire up the BBQ, or retreat to a quiet, dedicated workspace. Luxury, fun, and convenience all in one place.

Location · Family · Getting around

Headers’ Haven

Your family will be close to everything when you stay at this centrally-located in-law suite. Walking distance to beaches, shops, and restaurants. Steps from Steer Swamp Conservation Area. 13 miles from Boston, and an easy 10 min drive to Salem. Cool off in the pool during the summer heat, or relax in the hot tub on a chilly evening. There’s room for everyone on the pull out sectional to snuggle up for a movie night, complete with popcorn and candy machines. Sure to be a fun and cozy stay!

Value · Family · Pool

The Stunning Melita Farms Geodesic Dome Farmhouse

Your next stay awaits at the Melita Farms Geodesic Dome Farmhouse. The farmhouse is nestled off the beaten path (yet minutes from local gems) and is the perfect balance of retreat and convenience. Fall in love the moment you arrive on this 56 acre non-profit working farm to the moment you enter the front door. The farmhouse comfortably hosts up to 10 guests. Features 5 bedrooms, 2.5 bathrooms, hardwood floors, soaring cathedral ceilings, pool, and stunning farm views.

Location · Family · Cleanliness

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit, minutes from Singing Beach. This updated suite features a modern layout, fireplace, and two queen beds—one in a private sleeping area. Ideal for relaxing or remote work, with a secluded backyard, private entrance, free parking, and fast Wi-Fi. Near downtown Manchester-by-the-Sea, dining, and coastal views. Seasonal pool: 5/20–9/8. Walk to local shops, restaurants, and the harbor, all from this peaceful setting.

Value · Family · Checkout

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Family · Location · Kitchen

Cozy Studio | Pool | Espresso Bar

✨✨ About Our Studio ✨✨ Cozy private studio on the basement level (garage level – easy access). Peaceful stay, just 45–50 minutes from Boston. • 🏡 Private space • 📶 Wi-Fi • 🚗 Free parking • 🧺 Laundry access • 🏊 Seasonal pool • 🐾 Pets welcome (fee applies) ☕ Enjoy our premium Breville espresso machine for fresh espresso, cappuccinos & lattes. ✨ 28 min from Topsfield Fair ✨

Value · Family · Laundry