Holiday rentals with a kayak in Boston

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

Ipswich Riverfront Lodge|Sleeps 10|Kayak+Canoe

Enjoy a secluded retreat in nature all while being conveniently close to all the North Shore has to offer at The Ipswich River Lodge. The rustic style combined with modern amenities and multiple gathering spaces makes this the perfect spot for groups and families alike. Just minutes to downtown Ipswich and Crane Beach/Estate it's the perfect landing spot to explore all that Cape Ann has to offer! 10 Min Drive to Crane Beach 30 Min Drive to Salem Experience Ipswich With Us & Learn More Below!

Sunset Lake studio apartment. Kayaks for use!

Beautiful sunsets over the lake! 2 adult kayaks and 2 kid kayaks are available to guests. Light a fire at night. Play some yard games (corn hole, Bocce or Molkky). We are walking distance to South Braintree Square. You will enjoy nature and still have close proximity to city. Walk to a super market, pharmacy, nail salon, bank, a tavern w/ live music. Other restaurants within walking distance include Mexican, Thai, Sushi, Italian, Vietnamese (pho), pizza and a great local coffee shop. 🛶 🌅 🌆

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.

Revere Beach House, Logan Airport, Bay Views

Steps from Revere Beach, this home sleeps 6+ with sunrise views! Enjoy a private patio with firepit, grill, master suite with tub, and basement entertainment: 60" TV, wet bar, board & card games. 15 mins to Logan Airport (Uber ~$20). Fast WiFi, multiple WFH setups, full loaded kitchen, laundry w/detergent, parking for 2-4. Upstairs: king suite, queen & twin bedrooms rooms, office. Beach towels, 2 kayaks, linens, soaps all included. Relax by the fire or paddle out—your perfect getaway awaits!

Expansive coastal views, 3/2 newly renovated

Stella Serena has undergone extensive renovations. It is a completely renovated, charming, 3/2 home with most importantly, views of the marsh and waterways of Scituate from every window. Whether you are coming to unwind, kayak, go to the beach, or all of it, Stella Serena will give you the rare place to recharge & have fun. We provide bikes, kayaks, paddleboard, cornhole for fun. A firepit & gas fireplace for relaxation. Breathtaking, everchanging views daily and incredible sunsets.

Oceanfront Dock Escape ~ Kayaks & Paddleboards

This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, MA! • 13-minute drive to Wingaersheek Beach • 10-minute drive to Downtown Main Street in Gloucester • 2 inflatable Paddleboards • 4 Kayaks Available! • Outdoor Patio w/ Oceanfront Views • Large Jenga set • Fully Stocked Kitchen • Multiple Outdoor Spaces: Balcony/Deck • Family Friendly- Pack n Play & High Chair • Beach Essentials: Chairs, Umbrellas, Life Vests, Towels

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Boston Designer Beach House | Near Airport

Wake to ocean views, take a morning beach stroll, unwind on the deck, or perfect your swing on the golf simulator—all before sunset cocktails on the rooftop. This 2BR/2BA sanctuary sleeps 6 and blends breezy California vibes with curated vintage style. With a heated pool, firepits, co-working space, free parking, and steps to the train, airport, and beach, it’s your dream escape—just minutes from downtown Boston. The perfect mix of comfort, design, and unbeatable location.