Holiday houses in Raccoon Island

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Top-rated holiday rentals in Raccoon Island

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Top Guest favourite
The exterior of the home is captured under cloudy skies, displaying a two-story structure with navy blue siding and white trim. Stairs lead to an upper deck, while a small landscaped area is visible at the base. Snow covers the ground, adding to the serene ambiance.
Home in Weymouth
4.94 out of 5 average rating, 138 reviews

Newly remodeled home with ocean views!

Spacious home newly remodeled with all high end touches. This house has views of the Boston skyline and harbor Islands. Each bedroom and floor has it's own split system air conditioning for maximum comfort. Preferred neighborhood of North Weymouth which is 10 miles from Boston. This house provides a convenient location for you and your family to explore the city with all the comforts of home. Full laundry facilities are on the same floor with the bedrooms. 2 decks to relax and enjoy the views.

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 out of 5 average rating, 69 reviews

Waterfront Beach 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.

Top Guest favourite
An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.
Apartment in Boston
4.96 out of 5 average rating, 169 reviews

🎖The Ashmont Suite | Close to Subway + Downtown🎖

This high end & unique 3 bed / 2 bath unit is brand new, along with all the furnishings. It includes 1 King, 1 Double, & 1 Single size private bedrooms. The unit is extremely clean and remarkably decorated. Only a 5 minute walk to Ashmont station (red line), which takes you directly into Downtown Boston, Harvard Square, South Boston, Kendall/MIT, U Mass. There’s also plenty of parking available in front of the property. As well as a local coffee shop & a Dunkin just across Ashmont T station.

Guest favourite
A modern living area features a stylish orange sectional sofa, paired with decorative pillows. To the rear, the kitchen showcases stainless steel appliances, white cabinetry, and a dining space, while a staircase is visible in the background.
Home in Weymouth
4.91 out of 5 average rating, 136 reviews

Beautiful 3BR Home by the Water - Family Friendly

Welcome to our newly renovated 3-bed, 2-bath single-family home nestled in a serene and welcoming neighborhood in North Weymouth: • Walk to Wessagusset Beach and George Lane Beach • Just a 2-mile drive to Hingham Shipyard's dining, shops, and commuter boat to Boston • 11 miles from Downtown Boston • 3 miles from commuter rail or subway stations (bus #220, a 2-minute walk, takes you to Quincy Center or Hingham Shipyard) Ideal for families or groups seeking relaxation and easy city access.

Top Guest favourite
Guest suite in Norwood
5 out of 5 average rating, 20 reviews

Modern Upper-Level Oasis Minutes to Boston Stadium

Perfect for families or friends, this bright and stylish 3-bedroom upper level features a brand-new renovated kitchen with new appliances, a cozy living room with an electric fireplace, dining area, private laundry, a large deck, and 2 driveway parking spaces. Peaceful neighborhood near Boston and Gillette Stadium, quick access to the highway and Commuter Rail station to Boston in a 1/2 hour. The host lives on-site in the lower level of the house and is available for assistance if needed.

Guest favourite
A bright living area is showcased with large windows allowing natural light and a view of the ocean. Two comfortable sofas sit adjacent to a coffee table. The space features light wooden flooring and white walls, accented by soft curtains that gently frame the windows.
Cottage in Hull
4.91 out of 5 average rating, 23 reviews

Sunset Bay Retreat

Tranquil oceanside retreat, walking distance from the warm, smooth sands of Nantasket Beach. Enjoy unparalleled sunrise views and the cozy charm of this private home featuring two bedrooms, one bath, full kitchen, unique third bedroom loft area with double bed, smart TV, A/C, free Wi-Fi, washer/dryer and more. An easy stroll to dining, gift shops, popular outdoor boardwalk, historic carousel, convenience stores, and more. The perfect spot for romantic getaways or family fun!

Guest favourite
A spacious studio apartment features a king-size bed with colorful bedding and wall art. A futon is positioned near a circular coffee table on a patterned rug. Two small windows bring in natural light, while a ceiling fan ensures comfort.
Guest suite in Weymouth
4.8 out of 5 average rating, 330 reviews

Lovely studio on the coast! Beach close by!

Wonderful location located in north Weymouth. Quiet, Spacious studio apartment. Outdoor deck with patio furniture. Plenty of space for 3 guests max. - Walking distance to George lane beach & Wessagusset beach. - Convenience store, Pizza & Sandwich shop on our block. - 2 miles to Hingham shipyard - 5 miles to Nantasket beach - In between several commuter rail stations and across the street from a bus stop. - 4 miles to Quincy center - 30 minute drive to Boston!

Superhost
Apartment in Milton
5 out of 5 average rating, 19 reviews

Summer Escape in Milton | 2BR Near Blue Hills 14/1

🔥 SUMMER SPECIAL: SAVE UP TO 30% ON SELECTED STAYS! Escape to a peaceful summer retreat in Milton, just minutes from Boston and close to Blue Hills Reservation — perfect for hiking, scenic trails, outdoor adventures, and relaxing nature walks. • Blue Hills Reservation – 5 min (skiing, snowboarding, scenic winter trails) • Milton Village – 7 min (cafés & restaurants for a warm meal) • Quincy Center – 17 min • Downtown Boston – 18 min (easy access by car, bus & subway)

Top Guest favourite
The open kitchen and dining area feature a round dining table surrounded by four chairs. Natural light fills the space through large windows, illuminating the glossy stained hardwood floors. A decorative plant adds a touch of greenery, enhancing the overall inviting ambiance.
Apartment in Quincy
4.96 out of 5 average rating, 225 reviews

Short Train 2 Boston, Luxury prvt unit w parking

Enjoy a comfortable stay in this private entrance, beautiful, newly renovated 1 bedroom apartment only a short 4 minute walk to Wollaston train station- 5 stops to downtown Boston. Convenient access to Boston by car (15-20min) as well. Full gut-renovation, open floor kitchen/dining room. Gorgeous bathroom. New HVAC system. W&D in unit. Off street parking spot right next to separate, private entrance. Great neighborhood, beautiful park across the street.

Superhost
Apartment in Quincy
5 out of 5 average rating, 3 reviews

Spacious Beachfront Bliss, trails&walk Marina Bay

Beautiful newly renovated 2-bedroom apartment directly across from the beach with ocean views and coastal breezes. Spacious, stylish, and located in a quiet family-friendly area, perfect for a relaxing getaway. Enjoy scenic running and walking trails, walking distance to Marina Bay for waterfront dining, cafés, and marina views and close to the famous Tony’s Clam Shop. The perfect mix of comfort, location, and beachside charm.

Top Guest favourite
Home in Milton
5 out of 5 average rating, 11 reviews

Spacious 5BR Executive Retreat - 10 Min to Boston

Step into a home designed for professionals and families seeking a quiet sanctuary. At Cedar House, we've curated this space so you can simply unpack your suitcase and find that everything else you need is already here. With a coastal aesthetic, welcoming new furniture, tasteful decor, and warm wood floors, every corner of this 2,000 sq. ft. retreat invites you to relax and stay a while.

Guest favourite
Home in Weymouth
4.75 out of 5 average rating, 16 reviews

Bayfront Retreat with Private Ramp &Stunning Views

Make some memories at this unique and family-friendly place. This is a peaceful single family home with a private boat ramp that can also be used as beach access. Beautiful views of the bay and sunrise, the house has 3 bedrooms (sleeps up to 7, or utilize the couch on the sunroom to accommodate more), sunroom, garage, wood burning stove and outdoor seating. NON-smoking property.

Popular amenities for Raccoon Island holiday rentals

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Norfolk County
  5. Quincy
  6. Raccoon Island