Holiday rentals with a kayak in Boston

4.96 out of 5 average rating, 110 reviews

Cottage in Essex

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.

4.98 out of 5 average rating, 48 reviews

Home in Scituate

Beachfront Home Walk to Shops ! Incredible Views !

〰 SEPT-DEC '25 JUST OPENED 〰on 08/26 Welcome to Pebble House, 1-level beach house with Scituate HARBOR VIEWS. You will have private BEACH frontage to Museum Beach. ⛵ Go for a 15-min walk to harbor shops, restaurants or 10-min walk Scituate Lighthouse & The Barker. Swim and paddle in the bay off of your deck. Relax and enjoy views of Harbor boats & sunrises over the historic Scituate Lighthouse. 🌊 - 6 Min Drive to Minot Beach & 10 to Peggotty - 25 Mins to Rexhame, Duxbury & Nantasket Beach

4.84 out of 5 average rating, 96 reviews

Guest suite in Braintree

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. 🛶 🌅 🌆

4.96 out of 5 average rating, 26 reviews

Apartment in Cochituate

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

Apartment in West Medford

4.93 out of 5 average rating, 350 reviews

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.

4.81 out of 5 average rating, 27 reviews

Home in Beachmont

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!

5 out of 5 average rating, 33 reviews

Cottage in Scituate

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.

Guest suite in Lakeside Marblehead

4.8 out of 5 average rating, 35 reviews

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.

5 out of 5 average rating, 7 reviews

Home in Scituate

BOOK NOW! Walk on beach! Amazing views! Location!

Welcome to The Turner Tide, a peaceful coastal escape in Scituate, MA. Perched along the scenic shoreline, this charming home offers sweeping ocean views, salty breezes, and the soothing sound of waves—perfect for couples, small families, or anyone seeking a classic New England beach getaway. Sand Hills beach- less than a minute walk Scituate Lighthouse - 5 min Scituate Harbor - 5 min Museum Beach - 5 min Peggotty Beach- 8 mins drive Explore Scituate magic with us & Learn More Below!

4.83 out of 5 average rating, 47 reviews

Apartment in Scituate

ABC - Apartment by the Sea

This unique ground-floor studio, is your beach- and pond-side oasis. Dog-friendly Mann Hill and Minot Beach are right outside your door, w/ a pond the end of the garden! Full kitchen (-oven), a relaxing living area, and your own garden paradise. Fire pit by the pond, swinging chairs, outdoor dining area – the perfect spot to soak up coastal life. Scituate and Cohasset nearby. EV charger on-site King & queen beds (separated by staircase) ensures comfort for up to 4 adults + pets.

4.98 out of 5 average rating, 131 reviews

Guest suite in Concord

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)