Holiday rentals in Southborough

4.87 out of 5 average rating, 167 reviews

Home in Southborough

Luxury Living at its Best in X-Large 8 Beds Estate

The talk & admiration of the neighborhood. Airbnb Guests’ Favorite with over 130+ 5 Star Reviews. When you book, we aim to deliver everything that is described in order to earn the same 5 stars all around review from you. This large expansive 8 bedrooms, 4.5 baths estate home has had a complete renovation adding today’s high end touches, yet preserving old world charm. You will experience modern amenities, a massive kitchen & luxury living in a large open space. SORRY: We do not allow parties.

4.98 out of 5 average rating, 246 reviews

Home in Framingham

2BR—Lovely 1900s Home—1200sqft—25 Min to Boston

Welcome to our Charming 1900s House! 1200sqft 2nd/Top Floor Private Apartment @ our 3-Rental Property **Children 10+ Welcome** Granite Kitchen w/ Dishwasher - Fully Equipped w/ Essentials & Cookware Tiled Bathroom w/ Bathtub & Shower 2 Queen Bedrooms 2 Desks & Chairs Reclining Sofa & Glider Loveseat Laundry Room (Basement) Patio & Grill Driveway Parking—2 Spaces Private Entrance 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Park Deep Cleaned & Sanitized

4.97 out of 5 average rating, 261 reviews

Guest suite in Dover

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.

4.95 out of 5 average rating, 155 reviews

Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 2 futons and a mattress. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

4.97 out of 5 average rating, 191 reviews

Guest suite in Uxbridge

The 1780 Suite

Join us for a step back in time at our unique bucolic property. Set on a scenic road, the post and beam farmhouse was built in 1780 and offers a haven of peace and tranquillity after a busy day of exploring New England. Guests have a private entrance and wind their way up the period staircase to the second-floor suite with two bedrooms, a sitting room, a breakfast nook, and a bathroom. Enjoy your morning coffee outside on the Adirondack chairs as you contemplate the charms of country living.

5 out of 5 average rating, 239 reviews

Guest suite in Uxbridge

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Guest suite in Framingham

4.84 out of 5 average rating, 74 reviews

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

An exquisite and convenient I BR Modern suite nestled between Boston and Worcester is available for you. Bright and charm w/ a . Beautiful kitchen, remodeled bathroom and a bedroom. Private entrance w/ it’s lovely courtyard to sit outdoor, a free parking spot/ WiFi. The apartment is conveniently located to Babson and Wellesley College, both within 7 miles , FSU is 1 mile train station 2 miles , easy drive to Cape Cod. For all travelers & enjoy your stay her !

4.96 out of 5 average rating, 266 reviews

Flat in Framingham

Comfortable apartment in Framingham

Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

4.92 out of 5 average rating, 526 reviews

Flat in Hudson

Newly Renovated Apartment Near Downtown Hudson

Newly renovated private attic apartment near downtown Hudson with kitchenette, living room and bedroom/office. A warm, cozy space with plenty of natural light! Just upgraded to a new king sized bed! Free parking on site Walking distance to restaurants, cleaners, antique shops, roller skating, shopping center, gym, breweries, golf course... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

Guest suite in Marlborough

4.87 out of 5 average rating, 285 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Guest house in Shrewsbury

4.73 out of 5 average rating, 228 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.

4.95 out of 5 average rating, 55 reviews

Home in Framingham

Cozy en suite w/ high ceilings

Enjoy this peaceful oasis with backyard views of the tall pine forest and soothing sounds of a patio waterfall. Private entrance en suite features off street parking, air conditioning, easy access to major amenities. 10 minutes to Mass Pike. 5 minutes to Framingham State University. Very safe and easily walkable neighborhood. Use of propane fire pit upon request.

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Other great holiday rentals in Southborough

Private room in Southborough

4.89 out of 5 average rating, 122 reviews

Room with full bath, Queen bed

AlexRating, 5 stars3 weeks ago

Brilliant! Amazing stay, a very lovely family, very comfortable, clean, felt right at home! I would highly recommend! I was mindful of the quiet hours and their check-in/check-out instructions were easy to follow! They were very nice!!

Guest house in Shrewsbury

4.89 out of 5 average rating, 9 reviews

New Private Apartment

MadeleineRating, 5 stars1 month ago

Super beautiful and peaceful for our entire stay! I loved it! :)

Home in Framingham

4.9 out of 5 average rating, 10 reviews

Luxury HUGE House Near Boston | Big Groups

LoisRating, 5 stars10 months ago

Six couples just spent 4 wonderful nights in this gorgeous home. Can’t say enough about this beautiful residence. We had enough bedrooms and bathrooms for each couple. Our group spent a day in Boston then traveled up the coast to Maine for lobstering and whaling adventures. We loved the gourmet kitchen, cooked every morning and evening meal at the house. So much space to enjoy Our stay was 5* magnificent!!

Private room in Leominster

4.94 out of 5 average rating, 104 reviews

Private Leominster 3rd Floor Apartment

RajniRating, 5 stars2 weeks ago

I love Lenny’s Place and I’m so happy I found it. Lenny and his family are beautiful and good people. Lenny’s Mom Maria made me a beautiful dinner one evening I had asked for more towels and came home to find the towels and dinner. I grew up in Leominster but I hadn’t been back in 41 years. This was perfect for me and very close to town a 10 minute walk and a very short walk to Barrettes Pond right down the St. I used to swim there as a child. The surrounding area is stunning very green and many maple trees.

4.93 out of 5 average rating, 15 reviews

Flat in Framingham

Nice, Quiet, down town studio #2A

FainaRating, 5 stars2 months ago

Comfortable place in a great location. Exactly kind of place I was looking for to stay for a week at the great price. Easy parking.

4.97 out of 5 average rating, 102 reviews

Private room in Natick

Chateau Bro H2O Located on Lake Cochituate

KatherineRating, 5 stars3 weeks ago

We had a great stay at Rob and Kristin’s airbnb! Very clean and spacious, beds were comfortable, and we had everything we needed for a few nights stay. It was also conveniently located in a safe neighborhood.

Private room in Northborough

4.95 out of 5 average rating, 158 reviews

Swan Home with warm vibes - Guest BR & Pvt Bath

PeterRating, 5 stars1 week ago

Very nice place to stay. Quiet and peaceful. Hosts are friendly and responsive to any needs.