Watertown vacation rentals

4.87 out of 5 average rating, 109 reviews

A serene morning on the lake is depicted, with two individuals paddling a kayak through mist-covered water. The surrounding landscape features dense trees and gentle hills, while soft light reflects off the calm surface, creating a peaceful atmosphere.

Vacation home in Natick

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

4.96 out of 5 average rating, 303 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

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.

4.92 out of 5 average rating, 37 reviews

Cottage in Westford

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Condo in Lakeside Marblehead

An expansive view of the harbor is captured, showcasing numerous sailboats anchored in the water. Lush green grass and wooden benches frame the scene, with a flagpole standing nearby. A large tree casts shade on the area, contributing to a peaceful atmosphere.

4.99 out of 5 average rating, 174 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.

4.98 out of 5 average rating, 377 reviews

A multi-story coastal home is seen from a rocky shoreline, surrounded by lush greenery. Several white Adirondack chairs are positioned on the patio, enhancing outdoor relaxation. The gray exterior of the house features a large balcony with white railings, blending harmoniously with the natural landscape.

Apartment in Salem

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.

4.97 out of 5 average rating, 251 reviews

An open living area showcases a warm ambiance with string lights overhead. A dining table is set for six, and a cozy seating arrangement includes a colorful armchair and a plush sofa. A wall-mounted TV is positioned beside vibrant artwork against the white walls.

Condo in Salem

*Historic1710 2Br|Halloween Downtown+Parking

This stylish 2-bedroom home, designed by the homme team, offers a cozy retreat with Free parking onsite, for those seeking Salem’s spooky history and enchanting charm. The Archer House combines modern comforts with prime access to Salem’s best attractions, dining, and nightlife—perfect for families or friends. Explore the magic with iconic sites just moments away! 🕸 Hocus Pocus House - 5 min walk 🧙🏻‍♀️ Witch Museum - 5 min walk 🎃 Witch House - 10 min walk See below to discover more!

4.87 out of 5 average rating, 111 reviews

An aerial view captures the scenic coastline and sandy beach lined with boats. A variety of residential buildings dot the landscape, interspersed with greenery. The neighborhood showcases the charm of coastal living, with the sea and a pier visible in the background.

Apartment in Swampscott

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.

4.95 out of 5 average rating, 912 reviews

A wooden dock extends over the water, featuring a metallic ramp with handrails. The serene waters reflect the soft hues of a pastel sky, while residential homes line the shore in the background. Trees are visible, adding a natural element to the view.

Guest suite in Winthrop

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.

Guest suite in Lakeside Marblehead

A plush white bathrobe is hung on a hook, providing easy access for guests. Behind the robe, a well-organized shelf showcases an array of personal care products. A clean sink area with modern fixtures is visible below a framed mirror.

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.

4.86 out of 5 average rating, 178 reviews

The entrance to the bungalow features a welcoming wooden door with a decorative glass panel. Soft lighting illuminates the path and entryway, surrounded by well-maintained plants. Stone steps lead up to the door, creating a charming approach to the home.

Home in Beverly

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.

4.84 out of 5 average rating, 167 reviews

A compact kitchen is visible through an open archway, featuring modern appliances and wooden cabinetry. The microwave is installed above the stove, with a stainless steel refrigerator adjacent. The adjoining dining area includes a wooden table and chairs, with warm hardwood flooring extending throughout the space.

Apartment in South End

* 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.

4.95 out of 5 average rating, 171 reviews

The living area features a stone fireplace and a flat-screen television mounted above. The space includes a mix of comfortable seating, such as a blue sofa and patterned armchairs. Exposed wooden beams and a spiral staircase add architectural interest to the cozy environment.

Cottage in Stow

White Pine Cottage

Cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are visiting the area. Located in quiet neighborhood with very little traffic. Convenient to local farms, orchards, golfing, parks and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

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Popular amenities for Watertown vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Watertown's top sights

Star Market595 locals recommend

Porter Square143 locals recommend

Starbucks118 locals recommend

Fresh Pond Mall112 locals recommend

Mount Auburn Cemetery112 locals recommend

CVS100 locals recommend

Other great vacation rentals in Watertown

4.95 out of 5 average rating, 75 reviews

A bright living area features a comfortable sectional sofa alongside a coffee table, with natural light streaming through large windows. A smart TV is positioned on a wooden console. The entrance door leads to an inviting atmosphere, complemented by a high ceiling and coastal decor.

Bungalow in Hull

The Sunset Bay Retreat - Cozy Beach Bungalow

Home in Lakeside Marblehead

A serene view showcases the antique house reflecting in the calm waters of Redd's Pond. Lush greenery and trees frame the scene, creating a peaceful ambiance with clear blue skies above.

4.75 out of 5 average rating, 166 reviews

Walk to Everything Great about Marblehead!

4.92 out of 5 average rating, 13 reviews

Home in Wakefield

60 Jordan-New Construction Townhome

4.96 out of 5 average rating, 27 reviews

A view from an open door frames a pathway leading toward a coastal scene. The ocean is visible in the background, with a picket fence adding charm. Sunlight illuminates the outdoor area, highlighting the natural beauty of the surroundings.

Home in Swampscott

Master Suite with magnificent views of the ocean

4.97 out of 5 average rating, 151 reviews

A modern kitchen features a large island with seating for three, situated adjacent to exposed brick walls. Stainless steel appliances are prominently displayed, complemented by white cabinetry and a sleek countertop. Natural light brightens the space, highlighting the warm wooden flooring.

Apartment in East Boston

Nxt to ocean, 5 min dntwn by T

4.97 out of 5 average rating, 101 reviews

A private outdoor deck is set against a serene pond, surrounded by lush greenery and trees. A pathway of stepping stones leads from the deck to the water's edge, inviting guests to enjoy the peaceful natural surroundings.

Guesthouse in Westford

Detached Waterfront Guest House

4.99 out of 5 average rating, 81 reviews

A welcoming living area features a comfortable couch and armchair, arranged around a central coffee table. Natural light floods in through the patio doors, which reveal views of the serene meadow outside. A modern fireplace and wall-mounted television are also visible.

Apartment in Brighton

New 3 bedroom, 2 bath unit, meadow view!