Holiday rentals with a pool in Essex County

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

Private ADU• 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

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.

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!

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!

Cozy, with Lots of Space

Garden level guest suite in a quiet, single family home. Walk to commuter rail, downtown area, restaurants, and grocery stores. Ideal for an extended stay professional or graduate student seeking a private space. Fully furnished - a separate bedroom (king size bed), living room, bathroom, dining area, and kitchenette (sink, small fridge, microwave - NO STOVE). Includes 2 TVs with streaming service, wi fi, laundry, pool, and a monthly cleaning service. Off street parking.

Peaceful 2BR Haverhill Escape Fire Pit & Pool

🏡 Enjoy a cozy 2BR Haverhill retreat perfect for couples, families, business travelers, and extended stays near Boston. Relax with a King bed, Queen bed, private fire pit, seasonal shared pool access, and a fully fenced shared backyard. Inside, enjoy fast WiFi, Smart TV, a fully equipped kitchen, dining for six, and free parking. Conveniently located near commuter rail, downtown Haverhill, Merrimack River trails, restaurants, shopping, and easy Boston day trips.

Private Pool Retreat w/Fire Pit Near Singing Beach

Relax in a private coastal retreat with a pool and fire pit just minutes from Singing Beach. This updated suite offers a clean, modern layout with fireplace, comfortable sleeping space, and is ideal for relaxing stays or remote work. Enjoy a secluded backyard—rare this close to the beach. Located in Manchester-by-the-Sea near downtown, dining, and coastal views. Private entrance, free parking, and fast WiFi. Seasonal pool (5/20–9/8).

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

Cozy Studio • Near Boston

✨ ✨ About Our Studio ✨ Cozy and private renovated studio on the basement level (same level as garage — easy access). ⚠️ Please Note: The pool will be unavailable on July 4th. Perfect for a clean, comfortable and peaceful stay, about 45–50 minutes from Boston. • 🏡 Private space • 📶 Wi-Fi • 🚗 Free parking • 🧺 Laundry access • 🏊 Pool access (seasonal) • 🐾 Pets welcome (fee applies) ✨ 28 min from Topsfield Fair ✨

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!

Pool Is Open! Steps from Harbor + Walk to Old MHD

HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces