Holiday rentals with a kayak in Suffolk County

H&H Boston

Experience the best of Boston at our charming Mission Hill apartment! Enjoy easy access to the Green E line T station (3 minute walk) and the famous Jamaican pond. This well lit and spacious unit features a separate guest room, common eat-in kitchen/dining room combo! Perfect for medical professionals, tourists, Business and family visitors. Our apartment offers a comfortable, serene and relaxing stay in the heart of a vibrant Boston neighborhood. 10min walk from Brigham and Harvard medical sch.

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/pickleball/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

Serene Bright Private Bedroom in Deluxe Unit

From this home base, you will have the best of both worlds. Tranquility in and around the property while in close proximity to the delights of nearby Downtown Boston. Here you will be close to scenic trails, theatre, high quality food, museums, movie theatre, shopping, hospitals, institutions of higher education and more. The property offers a clean, comfortable and peaceful home-like environment. There is a long-term guest staying in unit's second bedroom. Both rooms are private and secure.

Cozy Apartment in Hingham

Quaint cottage-style space with two rooms, a porch, a private entrance and easy parking. Located under a mile from downtown Hingham with restaurants, shops, and a friendly pub. Across the street, you’ll find the Greenbush train into Boston and a five minute drive to the MBTA ferry. The space includes a comfortable double-sized bed, bathroom with outdoor shower, workspace and wifi. Additional amenities include air-conditioning, mini-fridge, french press coffee maker, tea kettle, and microwave.

Stella Maris, 6 bedroom coastal home, water views

Stella Maris is an inter-coastal sanctuary, located on a private, tree lined street, with ever changing views of Cohasset Harbor & surrounding marsh & waterways. The airy floor plan of this contemporary home is perfect for entertaining family and friends. Gathering on the deck at sunset is a favorite. A short walk to Minot Beach and the lovely Minot neighborhood. Close to charming Scituate & Cohasset Harbors with their great restaurant scenes. 5 minutes to the Commuter rail into Boston.

Cohasset Woodland Cabin

Private cabin tucked on a beautiful 10-acre property just 5 minutes from downtown Cohasset. Surrounded by more than 100 additional acres of woods, fields, and walking trails, the cabin offers a rare blend of seclusion and convenience. The property also neighbors Holly Hill Farm, a charming organic farm open to the community. This is a perfect retreat for guests seeking comfort, simplicity, and connection to nature—while still being close to Cohasset’s shops, restaurants, beaches, and harbor.

Lake House in the City

Experience the ultimate urban retreat with this stunning waterfront home on Lower Mystic Lake just minutes from everything in Cambridge and Boston. With breathtaking architecture and peaceful panoramic water views, you and your family will enjoy the city and nature in equal parts. Sun-filled living/dining area with floor-to-ceiling windows overlooking the lake, a gourmet chef’s kitchen, a pool, hot tub, direct lake access with kayaks and paddleboards, and easy parking/Ubers in to the city.

Best Beach and Backyard in Hull

Come enjoy the best part of Nantasket Beach and enjoy some fun family time in the backyard. Just minutes to the beach. We have beach chairs, beach towels and a beach cart to easily carry your things there. After the beach, rinse off in the outdoor shower and take a soak in the hot tub. Cook dinner on the grill and hang out around the fire pit. Close to the local grocery store, restaurants and shops. See the Guidebooks for recommended places to eat in Hull and getting to and from Boston,

Steps to Nantasket Beach: Waterfront Gem w/ Patio!

3 Mi to World's End | Walkable Location Escape to the water and make yourself at home at this waterfront condo just steps from Nantasket Beach in Hull. Ideal for couples, families, friends, traveling nurses, and working professionals, this 3-bed, 2-bath vacation rental features an equipped kitchen for effortless meals, comfortable living spaces to relax, and a patio with stunning water views. Start your mornings by the bay, spend the day at the beach, and hop on the nearby ferry to Boston!

Cambridge King Bed MIT Harvard Steps Away

Experience Cambridge luxury just steps from MIT and Harvard! This modern 2BR/1BA apartment blends comfort with convenience—perfect for academics, professionals, or travelers. Enjoy a stylish open living space, smart TV, fully stocked kitchen, and high-speed WiFi. Walk to Harvard Square, local cafés, and river paths, or hop into Boston in minutes. Thoughtfully managed with resort-style services, competitive fees, and guest-focused amenities for a seamless stay.

Every room water view new kitchen ferry to Boston

Make some memories at this unique and family-friendly place. 5 minute walk to commuter boat/ferry to Boston, Ma/Logan airport. Ferry ride is 15-30 minutes depending if boat is direct to Boston, MA or stops at Logan or Hingham. Please check ferry schedule as it changes to weekday only in the off season. The house is 28 miles south of Boston. Panoramic water views. Beach access across the street. Vacation or work from home with water views from every window.

Bright and open modern farmhouse

Modern farmhouse in a quiet neighborhood, near Rt. 2 and MBTA Redline. 4 spacious bedrooms, 2.5 baths, 3 floors of living with a yard, and al fresco dining on the back deck. Features a cook's gourmet kitchen, dining room, open floor plan with central AC, kayaks, paddle boards available with this rental. Ideal place for family and friends to gather just outside of Boston and next to Cambridge.