Holiday rentals in Middlesex County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlesex County

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

0 of 0 items showing

1 of 3 pages

Superhost

Holiday home in Natick

4.87 out of 5 average rating, 109 reviews

Private Lakefront with game room/Newly renovated

Ideal private location on crystal clear Lake Cochituate! Peaceful quiet spot w amazing view only 20 min to Boston & 1 or 2 min drive to anything u could need Fun game room &free use of tandem kayak & paddleboard and fishing Sliding barn door separates main king bedroom, bath, & open kitchen & livingroom from the back 2 queen beds, game room & bath Im always available to answer questions + provide tips, but I also respect your privacy & want u to feel comfy & independent 》25 6 person 3 car limit

Superhost

Home in Shrewsbury

4.92 out of 5 average rating, 13 reviews

Lake "Island" near Boston

This place is a hidden gem! It is a lake peninsula. Enjoy the amazing lifestyle on Lake Quinsigamond, while being close to the center of Worcester (only 10min). Even if you come to work in the area it feels like being on vacation. Lots of fun things all year around and only 40min to Boston, 1.5hr from Cape Cod. This 2 bedroom A-frame house and 1 BDR cabin are on a 5 acres property (2,000 feet of shoreline). Very close to UMass hospital, grocery stores, gym, restaurants, route 20 and I-90.

Guest favourite

Home in Westminster

4.9 out of 5 average rating, 182 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Guest favourite

Flat in Arlington

4.98 out of 5 average rating, 193 reviews

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Superhost

Flat in Cambridge

4.8 out of 5 average rating, 20 reviews

Elegant 3-Bed Oasis in Cambridge Near Harvard/MIT

Welcome to your Cambridge retreat! This spacious, newly remodeled 3-bdrm home plus futon offers 1,600 sq ft of stylish, light-filled space just steps from the Charles River and minutes from Harvard Square. With two and a half baths, it's perfect for families, business travelers, and friends. Enjoy scenic paths nearby, easy access to cafes, shops, and transit to Boston. Speedy Wi-Fi, smart TVs, and a fully equipped kitchen ensure comfort. Book now to experience the best of Cambridge and Boston!

Superhost

Cottage in Westford

4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Top guest favourite

Farm stay in Ashby

5 out of 5 average rating, 16 reviews

The Wellington House

Enjoy the exquisite natural beauty surrounding this beautiful historic getaway. Beautifully restored and maintained 1860 Farmhouse updated and fully appointed for your comfort. Property boasts fabulous views of 3 acre pond with private waterfall. Every window has views looking out over rolling fields and at horses grazing in adjacent pastures. Beautiful gardens, walking trails and a quintessential farm house porch for relaxing or work. The farm abuts hundreds of acres of State Wildlife land.

Guest favourite

Flat in Boston

4.97 out of 5 average rating, 151 reviews

Nxt to ocean, 5 min dntwn by T

Embark on an urban escape! Immerse yourself in our chic 2BR/1B + office retreat, ideal for up to 4 guests. Enjoy fast WiFi, steps away from an oceanfront park with stunning Boston skyline views. Walk to the Blue Line T station, one stop to downtown or the airport. Dive into our vibrant, safe historic neighborhood with restaurants, bars, yoga, sailing, and galleries. Not suitable for children, no parking/pets/smoking/cannabis/parties. Make this urban oasis your next unforgettable getaway!

Superhost

Flat in Boston

4.84 out of 5 average rating, 31 reviews

The Curie-Perfect for Monthly Stays

Experience Boston in a 1 bedroom with comfortable decor and charming feel! Just a 5 min walk from the T and close to Boston College/Harvard/MIT, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 55” Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed -> Balcony Ideal for business travelers, couples, nurses, and anyone looking to experience Boston in peace and comfort.

Guest favourite

Home in Westminster

4.94 out of 5 average rating, 127 reviews

Wachusett Mountain Get-Away

This family home is spacious and accommodating for those looking to relax while away from the ski slopes or simply wanting to get away from the city. Situated nearby a plethora of hiking and mountain biking trails, lakes for fishing and paddling, the home is perfect for those craving the great outdoors. The home is 6 min from Wachusett Mountain Ski Resort, 3 min from the Wachusett Brewery, and 1 min from the 1761 Old Mill Restaurant.

Guest favourite

Bungalow in North Andover

4.95 out of 5 average rating, 163 reviews

Luxurious Bungalow at Boutique Winery w/ Tasting

Escape to our 2-story Bungalow, perfect for couples, friends getaway, or professionals seeking a relaxing and exceptional retreat. The standalone building features a large living/kitchen area, full bathroom upstairs, and a spacious bedroom downstairs, with additional dining & sofa seating on the enclosed porch. Booking includes a wine tasting and 10% off all wine purchases, for an experience you'll always remember!

Superhost

Flat in Boston

4.84 out of 5 average rating, 167 reviews

* NEW Listing * A True GEM in South End , Boston!!

Experience Boston at its Best in this true gem apartment in the heart of desirable South End! Best Location! Best Neighborhood! Best bars and restaurants! A guests favorite in the neighborhood, you will fall in love of this charming 1 bedroom apartment with cozy and relaxing private patio in the heart of historical and trendy South End in Boston.