Holiday houses in Holbrook

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Top-rated holiday rentals in Holbrook

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Top Guest favourite

The outdoor deck provides a serene view of the waterfront at sunset, with vibrant hues of orange, pink, and purple filling the sky. Black metal chairs surround a small table adorned with a potted plant, creating a comfortable setting to enjoy the picturesque scenery.

Home in Weymouth

5.0 out of 5 average rating, 74 reviews

Waterfront Home With Attached In- Law Suite

Welcome to this beautiful stunning waterfront home with 2,847 sqft, 3 heating/cooling systems, attached In-Law Suite, cathedral ceiling, private beach and built in beach fire pit. Unreal scenery with the best view while being so close to Boston. Large deck overlooking the water and watch the amazing sunsets. The home is located near top attractions like Nantasket Beach and just 16 miles from Boston Logan Airport, 22 miles from Gillette Stadium. Kid playground is just feet away from the property.

ValueFamilyHospitality

Guest favourite

A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.

Home in Stoughton

4.93 out of 5 average rating, 159 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and limited on-street parking. Pet friendly!

LocationFamilyView

Superhost

Home in Randolph

5.0 out of 5 average rating, 4 reviews

Spacious Family 5BR Single House w/Parking 35

🔥 LIMITED-TIME DEAL: GET UP TO 20% OFF SELECTED DATES! ★ Entire spacious and private single-family home ★ 3 stylish living rooms with smart TV ★ 1 fully equipped kitchen + an kitchenette ★ 3 cozy dining areas ★ High-speed Wi-Fi ★ Central heating & AC ★ In-house laundry area ★ Fresh linens, towels, and essentials included ★ Parking: 2 cars in the garage + 4 reserved parking spaces A bright, roomy, and comfortable home ideal for family getaways, reunions, and group stays of up to 13 guests.

LocationBathroomSleep quality

Top Guest favourite

The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.

Guest suite in Sharon

4.96 out of 5 average rating, 234 reviews

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

Stunning CLG with private entrance, deck, & parking. •Bedroom #1 ground floor (2 guests only) has a Queen bed & smart TV with deck access. •Bedroom #2 upstairs is ONLY AVAILABLE FOR BOOKINGS OF 3–4 GUESTS and includes a Queen bed, smart TV, mini gym & office. •Living room with lake view & smart TV. •Bathroom with tub and sitting shower bench. •Fully equipped kitchen with stainless steel appliances. •Internet Access, You Tube, and Netflix. •Summer lake access.

ValueFamilyLayout

Guest favourite

Home in Randolph

4.92 out of 5 average rating, 12 reviews

Entire Private 6BR Single House w/Parking 35

SAVE UP TO 30% ON SELECTED DAYS! Welcome to your home away from home - a beautifully renovated, spacious 6-bedroom, 3-bathroom retreat crafted for comfort, connection, and relaxation. Ideal for family trips, reunions, and groups after exploring Boston. ★ Entire private single house ★ 3 modern living rooms with flat-screen TV ★ 1 fully equipped kitchen + 1 kitchenette ★ 3 comfortable dining areas ★ Central AC & Heating ★ Laundry area ★ Parking: 2 cars in garage + 4 reserved parking spaces

FamilyLocationSleep quality

Guest favourite

Home in Avon

4.98 out of 5 average rating, 41 reviews

Cozy 3BR Near Boston|Fire Pit|Sleeps 6|PetFriendly

Welcome to your boho bungalow 🌿 ✨ An earthy, cozy boho escape just 30 minutes from Boston. Perfect for families, couples, girls weekends & relaxed group stays. Large fenced yard for your furry friends! 🐶 This 3BR includes unique boho vibes, large open concept, fully equipped kitchen, cute dining lounge, parking for up to 3 cars in driveway + on-street available. Step outside to your private backyard oasis with a magical fire pit area & hippie she shed hangout to unwind & recharge stand

LocationFamilyCheckout

Top Guest favourite

The layout of the luxury in-law suite is displayed, featuring designated spaces including a bedroom, living room, kitchen, and dining room. The dimensions of each area are noted, along with a small deck, providing an overview of the suite's structure and flow.

Guest suite in Abington

4.89 out of 5 average rating, 356 reviews

South Shore Luxury Apartment

Luxury in-law suite with new appliances, new bed and bedroom furniture, heated bathroom floors, jacuzzi tub, electric fireplace, and off street parking just steps from your own private entrance nestled into the Ames Nowell State Park. Just minutes away from the South Shore Hospital, make this your home away from home! FireTV and an Echo Studio, all lights are controlled by Alexa. This apartment is not suitable for children. 2 hours Early Check-in/Late Check-out available $30

FamilyValueBeach

Guest favourite

An open living area is illustrated, featuring a light-colored sectional sofa with blue accent pillows. A large flat-screen television is mounted on the wall. A wooden coffee table sits on a patterned area rug, while a dining area is visible in the background.

Holiday home in Randolph

4.96 out of 5 average rating, 116 reviews

Built 2020 Private Home/4 Beds/2.5 Baths/EV Charge

Kick back and relax in this calm, quiet & stylish single new built home. Within 20-25 minutes driving distance to Boston downtown, Logan International Airport, Encore Casino, China Town, Financial District. 5-10 minutes away from Park & Ride shuttle to The Airport, 110 Grill, Legal Seafood, Five Guys, Starbucks, LA Fitness, Tavern in The Square, Bank of America, AMC movie theater, South Shore Shopping Mall, Chase Bank, BJ or Costco, Kohl’s, Olive garden.

ValueLocationBathroom

Top Guest favourite

Home in Brockton

5.0 out of 5 average rating, 78 reviews

Hot Tub, Gazebo, Pool table & Fire Table

Spacious, family-friendly retreat near Boston for up to 10 guests. Escape to your private backyard oasis, soak in the hot tub, shoot pool under the gazebo, gather around the fire table, or dine outdoors. Sleep comfortably with 1 king, 1 queen, 2 full beds, plus 2 fold-up queen mattresses. Enjoy Smart TVs, fast Wi-Fi, a fully equipped kitchen, and free driveway parking. Perfect for family trips, graduations, getaways, and business stays.

ValueLocationBathroom

Guest favourite

A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. Two lamps provide soft lighting. Mirrored closet doors reflect the room, and artwork hangs on the wall, adding a touch of character. Warm wooden flooring complements the neutral decor.

Home in Canton

4.94 out of 5 average rating, 109 reviews

Gorgeous 2nd Floor Home with Private Entry

Welcome to your home away from home! This beautiful second-floor 2 BR unit keyless self check in offers a private entrance and private stairs. Features: · Newly Installed AC · Fully Kitchen: Equipped with smart utilities, including an oven, microwave, dishwasher, washer, and dryer. · High-speed internet. · Comfortable Sleeping Arrangements: 2 beds & a sofa bed, perfect for accommodating up to 4 guests.

ValueFamilyPool

Superhost

Home in Brockton

5.0 out of 5 average rating, 6 reviews

Private studio suite – 25 Minuto from Boston

🏡 Cozy 1-BR basement apartment with private entrance, living room, kitchenette, bath, washer/dryer, Wi-Fi, A/C & free parking.📸 PLEASE CHECK EXTERIOR PHOTOS FOR STEP-BY-STEP CHECK-IN INSTRUCTIONS TO EASILY FIND THE ENTRANCE.🍳 Kitchenette: coffee maker, microwave, fridge, air fryer, blender, toaster, electric skillet & popcorn maker.📍 Quiet area 5 mins from the train station & 25 mins from Downtown Boston.

LocationIndoor spacesGetting around

Superhost

Home in Randolph

4.85 out of 5 average rating, 39 reviews

Quiet 1BR • Wi-Fi • Parking Included • In Randolph

Private 1BR basement near Randolph Center. Close to restaurants, fast-foods, cafés and a luxury cinema. Independent entrance with stairs, living room with TV, dining area, equipped kitchen, queen bedroom and renovated bathroom with walk-in shower. Wi-Fi included and parking for 2 cars. Great for short or long stays, ideal for couples, professionals and travelers seeking comfort and value.

LocationLong stayIndoor spaces