Guesthouse vacation rentals in Middlesex County

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Top-rated guesthouse rentals in Middlesex County

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

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Guest favorite

Guesthouse in Maynard

5 out of 5 average rating, 26 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

Welcome to the most walkable town in Metro Boston, w/ movie theater, live performance venue, beer garden, galleries, shops, & 17 restaurants 1/2mi from our front door. Our 1910 mill town company house is a little oasis. This is a two-family house; two separate private residences side-by-side. My family occupies the other side. Between house & garage, the outside dining area and fire pit are for your private use. Beyond the garage, we invite you to share our backyard w/ pool and badminton.

Guest favorite

Guesthouse in Andover

4.93 out of 5 average rating, 88 reviews

The Rose Cottage *Walkable to Downtown Andover*

Bright and charming free-standing cottage within walking distance to downtown Andover. Quiet residential street with easy on-street parking always available. One bedroom with a queen bed and TV with Hulu, Netflix, and more. Full kitchen with two-seat high-top table. Small den with couch, desk, and TV. Bathroom with shower stall. Private outdoor patio overlooking quiet woods. Walk to Phillips Andover, Merrimack College, and MBTA into Boston — come and enjoy this charming New England town!

Superhost

Guesthouse in Norwood

5 out of 5 average rating, 3 reviews

Spacious Suite 15 mi from Boston

This spacious two bedroom one full bath guest unit is all yours to enjoy and call home for your visit. This unit has 2 entrances, parking for 1 car, and a large capacity Washer/Dryer. The house is nestled behind an old mansion and surrounded by trees. It is close to markets and the center of town. The Commuter Rail makes 2 stops in town and will take you into Boston in less than a ½ hour. Gillette Stadium, Home of The New England Patriots and the popular Shopping Center is 7 miles away.

Guest favorite

Guesthouse in Newton

4.99 out of 5 average rating, 77 reviews

Sunny 1BR w views, close to BC and Boston

Newly renovated and furnished one-bedroom apartment on second level of historic carriage house atop Heartbreak Hill, and mere steps to Boston College, shops, and easy access to Boston via public transportation (MBTA Green Line). Offers panoramic views of Boston skyline, Boston College campus, Chestnut Hill reservoir and stadium. Features newly renovated kitchen, private laundry, air conditioning and a private terrace. This apartment is professionally cleaned between visitors.

Superhost

Guesthouse in Shrewsbury

4.79 out of 5 average rating, 68 reviews

Lovely & Spacious 2 BR (W/KING/QUEEN beds) 2 BTH.

Newly renovated unit. Bring the whole family for fun! This lovely and spacious 2 BDRM (1 King & 1 Queen beds) would be great for your family get away. Cook/bake while your family is away. 👶Baby crib available. Nice neighborhood to walk your dog 🐕 This would also be perfect for long term stays such us TRAVEL NURSE or working PROFESSIONALS. WORK from HOME! Entertain with HIGH SPEED WiFi/ROKU TV/NETFLIX. 3 mins to DEAN PARK. Easy access to UMASS, Route 9 & I-290

Superhost

Guesthouse in Shrewsbury

4.72 out of 5 average rating, 215 reviews

A Comfy Hilltop Home

Nice and comfy home with spectacular views and sunset! This house overlooks the rolling Worcester hills for miles and miles. Convenient location, quiet neighborhood, big backyard, expansive deck, and nearby scenic hiking trails. The house has 2 bedrooms, 1 kitchen, 1 full bathroom, washer & dryer, big deck, and lots of parking space. Beautiful and comfortable, with everything you'd need for cooking and relaxing.

Guest favorite

Guesthouse in Boston

5 out of 5 average rating, 21 reviews

Private Studio Guest House

Detached Studio Guest House with parking, in the rear of owner-occupied main home. Located on a quiet street in a vibrant neighborhood in the City of Boston. Ideal for solo travelers or couples! • 15 mins from Logan Airport & Downtown. • Steps away from MBTA Red Line. • Walk to nearby Restaurants, Cafes, Markets, Local Parks/Playgrounds, UMASS Boston, JKF Museum, Carson Beach, Castle Island.

Guest favorite

Guesthouse in Milford

4.97 out of 5 average rating, 35 reviews

The Stables on Silver Hill

Previously an actual stables and part of a former horse farm, this tranquil guest cottage sits far back from the road and neighbors nestled against 10 acres of wildlife-filled wetlands. It includes private, off-street parking and has very convenient access to major highways, shopping, eating, and entertainment, whether you're visiting for business or pleasure!

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 245 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

Guest favorite

Guesthouse in Newton

4.92 out of 5 average rating, 103 reviews

Private Carriage House near Newton Center and BC

Large studio above garage with private entrance located on famous Heartbreak Hill. Kitchenette with Fridge, Microwave, Keurig and full bathroom. Less than 1 mile to Boston College and just minutes to Cambridge and Boston. Easy walk to public transportation and Newton Center with great restaurants, bars, parks, and shopping. Free off-street parking.

Guest favorite

Guesthouse in Bedford

4.97 out of 5 average rating, 34 reviews

Guest suite in Bedford

Stay in a private, bright, spacious, and relaxing guest suite in Bedford, MA. Close to historic Concord and Lexington. You will be renting the entire suite to yourselves with your own separate entrance away from ours. Whilst the guest suite is attached to the main property, there is no direct access between this and the guest suite.

Guest favorite

Guesthouse in Westford

4.97 out of 5 average rating, 97 reviews

Detached Waterfront Guest House

Fully furnished and equipped rental in MA. This completely renovated detached private studio guesthouse is ideal with peaceful setting and your own private outdoor deck overlooking the pond. Located in the beautiful town of Westford MA. Just 35 to 40 min northwest of Boston and 10 minutes from the NH border. Five minutes to US Route 3.