Holiday houses in Watertown

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Top-rated holiday rentals in Watertown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Holiday home in Natick

4.87 out of 5 average rating, 109 reviews

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

Guest favourite

Cottage in Essex

4.96 out of 5 average rating, 100 reviews

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.

Guest favourite

Apartment in Winthrop

4.96 out of 5 average rating, 306 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Guest favourite

Home in Scituate

4.95 out of 5 average rating, 22 reviews

Button Beach Cottage

Capture the breeze of the coast at Button Beach Cottage! •5 min walk to beach. •Brand new remodel. •Family friendly. •Oceanview balcony. •Luxury bunk room. •Dedicated workspace. •Outdoor dining area on spacious deck directly off kitchen. •Access to lifeguard beach Primary BR: king bed, TV, reading nook, ocean view & balcony. BR #2: queen bed, dedicated work space, ocean view & balcony. Bunk room: 5 twin beds with play space. Full bath on each floor. Tub, standing shower, washer & dryer.

Top Guest favourite

Condo in Lakeside Marblehead

4.99 out of 5 average rating, 175 reviews

Harbor Hideaway

A uniquely detailed single-floor unit in a 2 unit house featuring a large kitchen/dining room, living room, and a private cozy veranda. Queen Bedroom & additional sleeping for 2 with a deluxe air mattress. This space is perfect for couples, families with young children, or a single person. Only one dog allowed no cats. This unit is on the lower floor of a two-family house occasionally you can hear steps from the upstairs. PLEASE note parking on site is very tight small cars compact SUVs only.

Top Guest favourite

Apartment in Salem

4.98 out of 5 average rating, 379 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Superhost

Apartment in Swampscott

4.88 out of 5 average rating, 112 reviews

Ocean views, Large Deck, Grill, Kid/Dog Friendly

The product of a complete gut renovation in 2020. The unit is 300 yards to Fisherman's Beach at the bottom of the street. The apartment is the 1st floor of a two family home (our family lives upstairs). It consists of 2 bedrooms, 2 full baths, pro kitchen, open living/dining area. The driveway can fit 2 cars (tight). There is additional parking at the bottom of the street. Please see house rules settings for holiday minimum bookings. We are pet friendly, but require case by case approval.

Guest favourite

Guest suite in Winthrop

4.95 out of 5 average rating, 913 reviews

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Superhost

Apartment in Ipswich

4.85 out of 5 average rating, 142 reviews

Lovely 3-Bedroom in Historic Dowtown Ipswich

Stay in one of our charming Airbnbs and experience the town's picturesque New England charm. Take a stroll down the main street lined with colonial-era houses and local boutiques. Visit the Ipswich River Wildlife Sanctuary and enjoy the famous Ipswich Restaurants, where you'll find the best food. Relax on one of the many nearby beaches, such as Crane beach, and soak in the sea, sand and sun. With so much to see and do, Ipswich is the ideal place to escape and unwind.

Guest favourite

Guest suite in Lakeside Marblehead

4.91 out of 5 average rating, 228 reviews

"Sweet 57" - private entrance suite

Suite with private entrance in quiet family home. Includes kitchenette with a microwave, mini fridge, and coffee maker. Washer/dryer available for week+ long stays (subject to host assistance). Includes access to family room with tv. Ample closet space. Beach chairs, towels, & bikes available. Come for a day or a week. You will not run out of things to do and will find your accommodations private, quiet and safe. NO SMOKING permitted in or anywhere near home.

Superhost

Home in Beverly

4.86 out of 5 average rating, 178 reviews

Beverly Beach House- Upper Deck

Half block from the beach in the scenic North Shore. Get away from it all in this beach bungalow. Close to downtown restaurants and shops, Historic Cabot theater and more. Large historic colonial home with 3 bedrooms and 2 bath with ocean views and off street parking. Large deck and full kitchen. 30 min train to Boston. Easy quick access to popular destinations such as Marblehead, Rockport, Newburyport, Gloucester and more.

Superhost

Apartment in South End

4.84 out of 5 average rating, 167 reviews

* NEW Listing * A True GEM in South End , Boston!!

Experience Boston at its Best in this true gem apartment in the heart of desirable South End! Best Location! Best Neighborhood! Best bars and restaurants! A guests favorite in the neighborhood, you will fall in love of this charming 1 bedroom apartment with cozy and relaxing private patio in the heart of historical and trendy South End in Boston.