Vacation rentals in Middleborough

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Top-rated vacation rentals in Middleborough

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

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Guest favourite

A living room area is depicted, featuring a green sofa and a wooden TV stand. Skylights allow natural light to fill the room, highlighting the warm wooden floor. In the background, a small kitchen can be seen through an open doorway, with two stools arranged at a counter.

Apartment in Bridgewater

4.84 out of 5 average rating, 264 reviews

Sun-Drenched 2BR Near Cape Cod & Boston Commuter

Welcome to a bright, comfortable 2-bedroom apartment just a 4-minute walk to BSU. Perfect for visiting families, traveling nurses, professors, and corporate guests. Enjoy private driveway parking, Wi-Fi, a fully equipped kitchen, and quiet residential neighborhood with a spacious backyard. located near Good Samaritan Medical Center and the VA, with easy access 2 Boston, Gillette Stadium, Plymouth, Rhode Island, & Cape Cod. A peaceful, homelike alternative 2 hotels for short or extended stays.

Top guest favourite

The entryway features a wooden staircase with white railings leading to the second floor. A cozy seating nook sits beside a window, adorned with decorative pillows. Light-colored walls complement the hardwood flooring, while a console table with a decorative bowl adds a welcoming touch.

Home in Plymouth

5 out of 5 average rating, 157 reviews

Updated Antique in Historic Downtown Plymouth

Updated antique colonial within walking distance to everything historic Downtown Plymouth has to offer- waterfront, boating, shops, restaurants, historic sites, and more. Fenced in backyard with patio overlooking gorgeous, well-maintained garden. Patio has large farm table with umbrella and Weber grill, great for entertaining! This charming in-town location offers you the best of both worlds - walking distance to everything while also being cozy and comfortable to enjoy a day at home to relax.

Top guest favourite

A view of a serene outdoor space featuring a green lawn bordered by a cranberry bog. A fire pit with chairs is situated in the foreground, while a rustic building and tree line create a picturesque backdrop under a cloudy sky.

Guest suite in Duxbury

4.94 out of 5 average rating, 103 reviews

Guest suite on cranberry bog, 1 mile from beach

Why fight the traffic to Cape Cod when you can enjoy New England's beaches, trails and seafood from beautiful Duxbury - just an hour from Boston! Our home is on a gorgeous cranberry bog surrounded by biking and walking trails and just a mile from the beach. Skylights and french doors to a private patio fill the suite with sunlight. Guests enjoy the fire pit, grill and yard in summer or hit the trails on snow shoes and sleds in winter. The bog freezes over too and is great for ice skating!

Top guest favourite

A stunning sunset paints the sky with vibrant colors reflected in the calm water of Woods Pond. The outdoor deck features seating arrangements, while two fishing poles stand ready for use by the private dock. Trees frame the serene view, adding a natural touch.

Home in Middleborough

5 out of 5 average rating, 54 reviews

Pelicans Bog on Woods Pond in Middleboro

Centrally located in Middleboro, this 3 bedroom house on Woods Pond is in a private community. Enjoy the massively spacious out door space while you fish directly off your private dock in the water. Kayak the pond with 2 tandem kayaks provided. Enjoy breezy dinners on the elevated deck overlooking the pond. There is an Air Hockey table located just off the basement bonus room or the foosball table inside. A dedicated large office space fully equipped and minutes to MBTA 1 hour to Boston.

Guest favourite

Apartment in Carver

5 out of 5 average rating, 10 reviews

Charming Retreat Amidst Carver’s Cranberry Bogs

Escape to the Heart of Cranberry Country! Nestled in the quaint town of Carver, Massachusetts – the self-proclaimed “Cranberry Capital of the World” – our two-bedroom apartment offers the perfect blend of cozy comfort and authentic New England charm. Kitchen is fully equipped, Wi-Fi, smart TV, and parking for two cars, you’ll feel right at home. The space sleeps up to 4 guests comfortably (5 with pullout couch). Step outside, and you’re yards from Carver’s walkable working cranberry bogs!

Guest favourite

A two-story home is presented, featuring a white exterior with multiple windows. A driveway extends in front, while a fenced-in yard offers a neat appearance. Lush greenery surrounds the property, enhancing the sense of privacy in this quiet neighborhood.

Home in Kingston

4.89 out of 5 average rating, 45 reviews

Cozy Modern 2BR near Grays Beach

Entire home for rent, filled with modern comforts from central ac to a sectional couch and a backyard pergola/patio. Free snacks and coffee. Cook, grill, or just use the best toaster oven ever. Darts, PS5, Meta VR, and Nintendo Switch. Kids activities! Trampoline, swings, and fenced in yard on a quiet street. No house parties. Close to highway, beaches, and historic Plymouth. This is our home when not rented. It’s fully furnished and comfortable. Updated throughout. 1 bathroom, upstairs.

Top guest favourite

A spacious grassy yard is bordered by tall trees, providing shade and a serene view of the lake. Sunlight glistens on the water's surface, and a small seating area is visible in the foreground, inviting relaxation in this picturesque outdoor setting.

Home in Pembroke

4.89 out of 5 average rating, 176 reviews

Lakefront House Boston, Plymouth, Cape Cod

Directly on the lake, with spectacular year round views. Perfect for a couple’s getaway or a family vacation. Its our family lake home where many special memories have been made & more are waiting! Home is about 15 minutes to historic Plymouth, 35 minutes to Boston, 20 minutes to coastal beaches, 40 mins to Cape Cod, 8 mins to Fieldstone show park & just 1 mile from the MBTA Halifax commuter rail station-takes you right into Boston or just stay & enjoy the lake. Private water access.

Superhost

A single-story blue house is set in a green, spacious yard, surrounded by tall trees. A curved driveway leads to the entrance, where a small garden is visible. A chimney rises from the roof, and a shed can be seen to the left of the house.

Home in Halifax

4.77 out of 5 average rating, 74 reviews

Lakefront Bliss,Your Perfect Getaway on the Water.

Welcome to our charming lakefront Airbnb! Nestled on the shores of Monponsett lake, this cozy retreat offers breathtaking views and a peaceful escape from the hustle and bustle of everyday life. With comfortable accommodations for up to 6 guests, our Lake front features a fully equipped kitchen, a spacious living Room, fireplace, private deck overlooking the water. Enjoy a morning coffee as the sun rises over the tranquil lake, or unwind in the evening with a bonfire by the shore.

Guest favourite

A cozy bedroom features a spacious bed adorned with a checkered blanket. Light enters through a window with sheer drapes, while decorative wall art and shelves add to the rustic charm. A round rug complements the hardwood floor, enhancing the welcoming feel of the space.

Apartment in Taunton

4.96 out of 5 average rating, 132 reviews

World Cup Special* 25 Mins to Boston* Stadium

This warm and inviting, rustic style apartment is located in the Historical district of Taunton, prime location for all the “Hotspots” of Mass. Minutes to routes 24, 44, 495, and route 138. Perfect for long term stays/Short term or traveling nurses! Your home-away-from-home awaits you! We provide Free: ✔Coffee, also decaf/Tea ✔WIFI ✔Netflix/ cable/Disney+ ✔Snacks ✔Basic cable ✔Quality toiletries and soaps ✔Iron/Ironing board ✔Board games ✔Level 1-2 EV charging port

Guest favourite

A serene lakeside view features calm waters reflecting pastel hues of the sunset. Smooth stone pathways lead to a grassy area, where comfortable seating arrangements are visible. The landscape is framed by trees, adding a natural element to the tranquil outdoor setting.

Home in Lakeville

4.87 out of 5 average rating, 70 reviews

Lakefront Retreat -Private Dock+Kayaks on the Lake

Escape to Long Pond, Massachusetts’ premier fully recreational lake. This beautifully renovated 3-bedroom, 2-bath waterfront retreat features a private dock plus kayaks, canoe, rowboat, and paddleboard for your enjoyment. Swim, boat, jet ski, fish, water ski, tube, or simply relax by the water. Conveniently located within 30-45 minutes of Cape Cod, historic Plymouth, downtown New Bedford, beaches, restaurants, and many of Southeastern Massachusetts’ top attractions.

Superhost

A lakeside view of a charming home with large windows, surrounded by lush greenery. A stone patio features seating arrangements with a pink umbrella, while the shoreline is visible in the foreground. Calm waters reflect the structure, enhancing its serene atmosphere.

Home in Lakeville

4.81 out of 5 average rating, 36 reviews

Shoreline Dreams

Welcome to your dream vacation getaway! Nestled on the serene shores of Long Pond, this charming lakefront home offers the perfect blend of comfort and natural beauty. Step inside to a spacious, open-concept living area adorned with large picture windows that provide breathtaking views of the sparkling water. Outdoor chairs with firepit offer panoramic views of the lake. The private dock is perfect for swimming, fishing, or launching kayaks and paddleboards.

Top guest favourite

A handcrafted tree house is perched among trees, supported by wooden stilts. The structure features a rustic exterior with a metal roof and large windows, surrounded by greenery and vibrant pink flowers in the foreground, creating a serene and natural setting.

Treehouse in Wareham

4.97 out of 5 average rating, 231 reviews

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.