Holiday rentals with a kayak in Essex County

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!

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.

Downtown w parking, beach, shops

Enjoy our fully refurbished historical home located in the heart of the coastal town of Rockport, Massachussetts. Perfect for couples or small families. This cozy basement unit offers a comfortable stay with with parking and a new kitchen, bathroom and washer and dryer, Our unit features a bedroom with a comfortable king size bed, The living space is tastefully decorated with a queen sofa bed. Walk to the beach, Bearskin neck, restaurants, Shalin Liu music center, art galleries and shops.

Spectacular pond view, suite on conservation land

Imagine sipping morning tea or coffee gazing at the view of the pond across the street. Or maybe relaxing in a screen porch watching yellow finches and hummingbirds flittering around the yard in season. Explore the trails on 180 acres of conservation land out our backdoor. Delight in the changing colors of leaves in the fall, and the sounds underfoot. After exploring Cape Ann or our award winning beaches, or dining on fresh New England seafood, how about a sunset canoe ride on the pond?

The Bungalow Luxe & Cozy Retreat by the Sea

The Bungalow is a coastal chic dream built for two! A newly updated & thoughtfully designed gem, nestled at the northern-most point of Plum Island, Newburyport, MA (not more than 100 paces from the ever watchful beacon of the famous Plum Island Lighthouse). Whether relaxing at the beach, paddling around the Basin, biking to one of the island stores or restaurants , or simply exploring the pristine Federal Wildlife Refuge, a special experience & adventure awaits you at The Bungalow!

Harborside Hideaway Guest Suite

Charming, private guest suite attached to a historic Colonial in the heart of Old Town. Guests love its quintessential New England charm and prime location. Take in stunning coastal views just steps outside the door of your private entrance. Walk or bike to shops, bars/restaurants/cafes, beaches & historic landmarks. Minutes to bus & commuter rail. Great for couples, solo travelers, visiting professors, or parent(s) with infant or young kids. Please inquire about accommodation options.

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

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Le Elona – Private Island Stay on Historic Land

Welcome to Le Elona – a hidden guest suite on a private ¾-acre island in Peabody, MA. Just minutes from Salem, this peaceful retreat offers full privacy, scenic water views, and a cozy, stylish space with its own entrance and bath — no shared areas. Perfect for romantic getaways, solo escapes, or remote work. Once owned by Giles & Martha Corey of the Salem Witch Trials, with their memorial just a 2-minute walk away. A truly rare and unforgettable stay awaits you.