Holiday houses in Raccoon Island

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Top-rated holiday rentals in Raccoon Island

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Guest favourite
A outdoor deck features a round dining table and two chairs, positioned under a large umbrella. A side chair rests nearby. The scene is complemented by a colorful seasonal welcome mat, while a view of the expansive green yard and trees is visible in the background.
Apartment in Weymouth
4.84 out of 5 average rating, 57 reviews

Spacious 1-Bed Apt. in Peaceful Weymouth W/Balcony

Spacious and sunlit 1-bedroom apartment in a peaceful Weymouth neighborhood, featuring a private balcony and relaxing views.Perfect urban retreat for relaxing or working from home, blending quiet natural beauty with excellent proximity to local seaside parks and easy Boston commuting.Open-concept layout featuring oversized windows that flood the apartment with natural light & connect directly to your private balcony offering quiet, peaceful views, perfect for morning coffee or evening unwinding.

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, 144 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.

Superhost
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, 152 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 abundance on-street parking. Pet friendly!

Guest favourite
A serene view of the water at sunset, with soft hues of pink and purple in the sky. The silhouette of the Boston skyline is visible in the distance, alongside a small boat gently floating on the water's surface.
Guest suite in Quincy
4.89 out of 5 average rating, 83 reviews

City Escape By the Water

Cozy and fully updated guest suite right on the water. This is located a short 15-minute drive by car or a bus from Quincy Center on the red line. You will have a separate entrance to the suite and your private full bathroom and living room area. It’s a cute studio designed for two! Feel free to use our desk and deck with direct waterfront access and enjoy the beautiful sunsets with Boston skyline. We have added FireTV from Amazon! FYI there is some road noise. And it’s an attached 2nd unit.

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, 139 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
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop
4.95 out of 5 average rating, 1,047 reviews

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with 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.

Top Guest favourite
The exterior of a stylish two-family home is depicted, featuring a welcoming porch with white railings and a neatly landscaped front yard. Flowering plants, small trees, and a paved pathway lead to the entrance. The upper floor includes strategically placed windows, allowing natural light to filter in.
Apartment in Winthrop
4.95 out of 5 average rating, 110 reviews

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

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
4.92 out of 5 average rating, 26 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!

Top Guest favourite
The image captures a scenic aerial view of Nantasket Beach, showcasing a long sandy shoreline bordered by calm blue waters. The landscape features residential areas, patches of greenery, and distant islands. The expansive sky is bright with clear blue hues, enhancing the coastal atmosphere.
Guest suite in Hull
4.9 out of 5 average rating, 29 reviews

The Number 4 House

Welcome to the Number 4 House located in beautiful Nantasket beach! This family friendly home offers two bedrooms + bonus bunk bed room. Walk to downtown Hull in 3 min, beach in 6 and main strip with bars and restaurants in 15. Get to Boston & Logan airport on fast ferry in 25 min! Perfect entertaining backyard with grill, lounging patio and gas firepit. Sleep comfortably with central AC. Wash, dry & fold laundry services also included upon request . Come stay & play!

Top Guest favourite
A serene view of the ocean horizon is captured during twilight, showcasing soft gradients of color from orange to blue in the sky. The coastline is visible with a curve of land meeting the calm waters, surrounded by lush greenery and a few architectural structures.
Apartment in Hull
5 out of 5 average rating, 79 reviews

Cozy Coastal Apt w/ Ocean View Patio & Fireplace

Escape to the charming and historic town of Hull! This ocean-facing studio is the epitome of relaxation: a plush king bed, private patio, fireplace, huge TV, and a spacious bath. Enjoy complete privacy and convenience featuring free parking, walking distance to Nantasket Beach, local restaurants, and shops within a short drive (or ferry!) to Boston. Don't miss your chance to soak up the gorgeous weather in one of the most unique and picturesque properties on the MA coast!

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
4.81 out of 5 average rating, 342 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!

Guest favourite
Guest suite in Milton
5 out of 5 average rating, 7 reviews

Guest Suite in Milton

This private suite features 2 comfortable bedrooms with cozy bedding. The suite includes a fully equipped kitchenette stocked with essentials for preparing meals. A clean, modern bathroom is supplied with fresh towels and basic toiletries for your convenience. It’s perfect for small families, couples, or business travelers. Enjoy complete privacy with your own separate entrance from the main house, allowing you to come and go as you please without disturbance.

Popular amenities for Raccoon Island holiday rentals