Holiday rentals with a hot tub in Medford

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.

World Cup ready, with private 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!

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!

Amazing Location in Little Italy with Roof Deck

Our fully loaded one bed is centrally located in Boston's North End (Little Italy) on land that was previously American Patriot Paul Revere’s bell foundry. The unit features a spacious roof deck with views of Boston Harbor, the USS Constitution, and the USS Cassin Young. It is within 10 minutes walking distance to 50+ restaurants, TD Garden, the Freedom Trail, and the subway. It is also within walking distance to the Boston Common/Public Garden and many of Boston’s most visited attractions.

Cozy Waterfront 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.

Charming 3BR Boston Stay Garage + EV + Pool Table

✨ Welcome to The Enchanted Willow — a Boston stay minutes from downtown. 25 min to Gillette Stadium ⚽ • 10-min walk to train • 4-min walk to bus • walk to cafés, restaurants & Roche Bros Private garage parking + EV charger (rare in Boston) + pool/ping pong table. Quiet neighborhood with vintage New England charm—perfect to unwind after a full day out. Ideal for families, couples, or friends. Traveling with a larger group? Ask about our second unit—up to 14 guests.

Historic home on Salem Neck

Home away from home! Pristine, high-end, fully renovated first-floor unit part of our two-family home. Comfort, privacy, and convenience in prime Salem location. Walking access to everything Salem, no car needed, close to train. Fully equipped kitchen, 2 bedrooms 2 full bathrooms, relax indoors or out. Quiet residential neighborhood, steps from Common and small public beach. Please note: no pets, no smoking, no events-parties. We can accommodate up to 4 guests.

1 BR full apt w/ private hot tub, yard; sleeps 4

Private ground level 1 BR apartment with kitchen, living room, and 2 full baths. Small yard w/ grill & hot tub; enjoy year round! Walk to MIT (5 min) Central Sq subway (5 min) Harvard (10 min) Fenway (30 min) bike rental (2 min). Great for vacations, events in town, or for quiet workspace weekdays between 8am-5pm. Comfortably sleeps 4 in 2 private rooms, each w/ own bath. Parking is not available at the property; closest pay parking is Green St. garage.

Lux Colonial Home:Game Room, Home Theatre, Karaoke

Experience classic New England charm in this beautifully restored 4BR, 2.5BA Colonial in Framingham. With 2,500+ sq ft of bright living space, a fun game lounge, and a sunny backyard patio perfect for BBQs and morning coffee, it’s ideal for families and groups. Located just 30 minutes from downtown Boston, enjoy easy access to the city while relaxing in a peaceful suburban retreat designed for comfort, connection, and memorable stays

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!

Cozy & convenient place with sunset & garden view

Clean, quiet, and airy private suite in a safe and quiet neighborhood in Waltham. You’ll find almost all amenities just like home. A few mins away from shopping malls, great restaurants, groceries in Moody st., and booming biotech hub in Waltham, and all major highways. 15-20mins to downtown Boston and airport. Scroll down for my guidebook and personal favorites. Reach out if you have any questions