Holiday rentals with a hot tub in Essex County

Mansion in Gloucester with Pool

Entire Mansion in the most coveted neighborhood in Gloucester, with private backyard, Pool, Tennis /pickleball court, 2 car garage in a quiet neighborhood, 3 min walk to waterfront, access to beaches, restaurants, bars and the best of everything New England - Gloucester have to offer. 4 Bedrooms, 4.5 Baths, sleeps 12, Master Suite with Jacuzzi. 10 min walk to Niles Beach, 10 mins scenic drive to Good Harbor beach. Private backyard deck with a pool, for family cookout and stroll to get ice cream

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.

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

By the Ocean - Egg Rock House - 4 bed 4.5 bath

Egg Rock House, a "wicked awesome" New England location. Walk to restaurants & shops, outdoor activities, nightlife, and trains to Boston or North to Maritime towns. Ocean views, the chef's kitchen, high ceilings, large tiered decks. 4.5 miles to Salem. Jacuzzi tub in Master Suite, gas fireplace in living room. every bedroom has its own bathroom! Off street parking for 2 cars. Visit nearby towns Salem, Marblehead, Gloucester, Rockport, take the train 25 minutes to Boston or park at T station

Large Modern Townhouse Condo with Roof Deck

A luxury condo that you would love to call home. A distinctive and stunning restoration of the historic Hibernian Hall. A gorgeous granite kitchen featuring stainless appliances, maple cabinets, and pendant lighting in a wide-open floor plan provides a wonderful environment for gracious entertaining or those private family dinners. Notes: The 3rd bedroom is a den off the kitchen with a brand new memory foam mattress. This room is set up as a double bed bedroom. Also, one-week min in season.

Salem, Boston, Fall/ Winter escape with hot tub!

Close to everything Boston has to offer when you stay at this centrally located home! Local restaurants, wholefoods, and the T which takes just minutes to get to Boston for ice-skating, Fauniel Hall, the Freedom trail, and the north end. Great location whether you're catching a Bruins/Celtics game or touring colleges or school vacation week away. Unwind and let the powerful jets relax you in our beautiful outdoor hot tub. Come see why Melrose is rated one of the top cities, you will love it!

5BR Luxe Lakehouse: Theater, Gym, Spa, Bar, Garage

Lakeside ease with modern comforts. A classic New England lake house, it was originally constructed as a haven for summer and winter getaways. Completely renovated in 2023, this timeless property blends cutting edge technology and infrastructure with its rustic charm. It showcases brand new furniture, fixtures, and equipment and has a private theater, gym with connected fitness technology, bar, game room, and spa. A luxurious, tranquil getaway where you can unwind and create lasting memories.

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!

Gingerbread House | Hot Tub | Dog Friendly

Our historic carriage house in Downtown Rockport has everything you need for the perfect getaway, all year long! A two-minute walk to beaches, shops, galleries, parks, and playground. A peaceful family and pet-friendly space with all the amenities you need for a comfortable stay: laundry, full kitchen, queen sized bed with en-suite bathroom and a sun room that converts to an extra sleeping space perfect for kids. A 5 minute walk to the train for day trips to Salem, Gloucester, and Boston!

Plum Island - Luxury Beach House

Fully remodeled 3 bedroom house, on a quiet street away from the main road on Plum Island, just 1 block from the beach. The rooftop deck provides wonderful sunset views over the marsh/basin , and beautiful sunrise views over Plum Island Beach. Enjoy the night sky while relaxing in the hot tub! It is walking distance to island restaurants & stores, and is a very short drive to the Parker River National Wildlife Refuge. Bonus room in basement with smart TV , firepace and loveseat.

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!