
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.

Cute & Cozy Groton apartment w/private patio
Cozy apartment with your own private patio; 5-min walk to downtown, shops, cafes, library & restaurants; hop on the Nashua River Rail trail where you can walk/bike to neighboring towns. Enjoy all Groton has to offer, miles of hiking trails, rent a canoe or kayak, golf, horse riding, fishing, apple, pumpkin & berry picking; walk up to Bancroft Castle on Gibbet Hill where “Little Women" was filmed & enjoy the view. Don’t miss a visit to Groton Hill Music, our world class music performance venue 🎶

Modern 2BR with A/C for your Business and Pleasure
Ideal location for business travelers or small families. Enjoy a comfortable experience at this centrally-located place. Don’t be fooled by the size of our 600SF home, it has everything you could need - fast WIFI, fully stocked kitchen, central AC, gas stove, insta hot water, fridge with ice & filtered water on the door, and a soaking tub. Conveniently located by Hanscom AFB, Hartwell Business Corridor, Wiggins Ave Technology District, MIT Lincoln Lab, Edge Sports Center & the Minuteman Bikeway.

Peaceful Country Home, Dover, Ma: Private Entrance
Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Just Renovated, Private & Quiet 2 Bedroom Condo
Keep it simple and comfortable at this peaceful, centrally located getaway. Set at the very end of a private, ultra-quiet dead-end road, the home feels tucked away This newly renovated 2-bedroom unit is an ideal home base for your Boston-area stay You’ll have easy access to public transportation, parks, dining, shopping, and major highways including I-95, I-90, and Route 2. Enjoy your own private outdoor deck, a spacious yard, in-unit laundry, central AC, and off-street parking for two cars

Cozy en suite w/ high ceilings
 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

White Pine Cottage – Cozy 3BR w/ Fireplace
Welcome to White Pine Cottage - a cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are coming to the area to visit family, work or a weekend getaway. Located in quiet wooded neighborhood with very little traffic. Relax by the fireplace and enjoy a soak in the whirlpool tub. Convenient to local farms, orchards, golfing, wooded trails and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Comfy-Spacious-private 1BR conveniently located
This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

Large One Bedroom Apartment
1,100 square feet, completely renovated, 1 bedroom with a walk-in closet. Large bathroom with two sinks and walk-in shower. Open concept living, dining and kitchen area with vaulted ceiling. Hardwood floors throughout. Central air. Apartment is connected to a main house but with no interior access between house and apartment whatsoever. (No interior connecting doors at all) It has its own private driveway and side yard. Reef tank will no longer be in the apartment after May 20th.

Newly renovated, spacious, clean, 3 bedroom home.
Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Water front cabin-like guest suite on a quiet pond
Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Private Mother-In-Law apartment on the lake!
Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

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.
Popular amenities for Middlesex County holiday rentals
Other great holiday rentals in Middlesex County

Enchanted Willow Boston Storybook Stay 3BR Parking

Garden Paradise Retreat in Marlboro

Rare, Private 2-Bed near Historic Wayside Inn!

the house of id; vintage shop, accessible space

2 BR Suite, Private Entrance, Woodlands, Quiet

Stay in the Heart of Fenway & Berklee

Gorgeous Guest Suite in Weston

Modern Studio w/ Fire Pit, Play Area & Large Yard
Destinations to explore
- Apartment rentals Middlesex County
- House rentals Middlesex County
- Rentals with an EV charger Middlesex County
- Smoking-friendly rentals Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with beach access Middlesex County
- Private suite rentals Middlesex County
- Loft rentals Middlesex County
- Rentals with a firepit Middlesex County
- Rentals with a cinema Middlesex County
- Rentals with an accessible-height toilet Middlesex County
- Rentals with a fireplace Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with lake access Middlesex County
- Hotel rooms Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with a patio Middlesex County
- Bed and breakfasts Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Beachfront rentals Middlesex County
- Rentals with a kayak Middlesex County
- Flat rentals Middlesex County
- Serviced apartment rentals Middlesex County
- Rentals with an accessible-height bed Middlesex County
- Rentals with outdoor seating Middlesex County
- Cottage rentals Middlesex County
- Rentals with breakfast Middlesex County
- Waterfront rentals Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with pools Middlesex County
- Townhouse rentals Middlesex County
- Guest house rentals Middlesex County
- Boutique hotels Middlesex County
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- Revere Beach
- Northeastern University
- Boston Seaport
- Boston University
- Freedom Trail
- New England Aquarium
- MIT Museum
- Boston Convention and Exhibition Center
- Monadnock State Park
- Gillette Stadium
- Duxbury Beach
- Canobie Lake Park
- Crane Beach
- Quincy Market
- Museum of Fine Arts
- North Hampton Beach
- Roxbury Crossing Station
- Prudential Center
- Things to do Middlesex County
- Sightseeing Middlesex County
- Food and drink Middlesex County
- Art and culture Middlesex County
- Things to do Massachusetts
- Art and culture Massachusetts
- Nature and outdoors Massachusetts
- Food and drink Massachusetts
- Sightseeing Massachusetts
- Things to do United States
- Tours United States
- Food and drink United States
- Art and culture United States
- Entertainment United States
- Wellness United States
- Sports activities United States
- Sightseeing United States
- Nature and outdoors United States




