Holiday rentals with a hot tub in Essex County

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.

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!

Charming Beach Home with Jacuzzi and Fireplace

Discover your seaside haven on our breathtaking waterfront! Perfect for couples or intimate family getaways, this two-bedroom sanctuary grants private ocean access just steps away. Bask in panoramic views and let your cares drift away in the brand-new jacuzzi perched above the horizon. Conveniently located between Salem and Boston, you’re only 30 minutes from both historic towns. Immerse yourself in the rich tapestry of Boston’s North Shore and create lasting memories.

4Bed AP/5 min walk to blue line downtown to Boston

Modern comfort in the heart of Boston ! This stylish 4BR/1BA apartment sleeps up to 8 guests with 2 queen beds 1 king bed and a queen sofa bed. Just a short walk to the Blue Line T, offering fast access to Logan Airport, downtown Boston, and Revere Beach. Enjoy a fully equipped kitchen, fast WiFi, smart TV, and thoughtful touches throughout. Parking available via SpotHero or nearby street options. Professionally cleaned and disinfected before each stay.