Holiday rentals in Westwood

4.97 out of 5 average rating, 114 reviews

Home in Stoughton

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and unlimited on-street parking. Pet friendly!

4.99 out of 5 average rating, 163 reviews

Guest suite in Weston

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 15-minute drive to Amtrak's "Route 128" station to NYC and points south.

4.97 out of 5 average rating, 262 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.

4.79 out of 5 average rating, 128 reviews

Flat in Dedham

Lovely 2 bedroom apartment minutes from Boston

Book your stay at this peaceful and townhouse-style apartment just minutes from Boston. This renovated space features 2 bedrooms (one queen bed and one full bed), one full bath with glass shower (second floor), living room with pull out sofa, and eat-in kitchen with designated work space. Take advantage and relax by the outdoor fire pit (reservations required) or walk to Dedham Square for food and shopping. Dates you need not available? Make sure to check out our other listing next door!

4.96 out of 5 average rating, 195 reviews

Flat in Dedham

Two bedrooms, full bathroom, and breakfast room

We offer the entire second floor of our home: two bedrooms, each with a queen-size bed, a full bathroom, and a well-stocked breakfast / snack room. We are located literally seconds off Rt. 128 / I-95, in a quiet, secluded area. Our deck, gardens and grounds (which include a pond, birdfeeders, and, perhaps, wildlife sightings) are available for your enjoyment. You will have complete privacy in your quarters, but we will be close at hand should you need advice or service. Gretje and Bob

Place to stay in Sherborn

4.97 out of 5 average rating, 297 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

4.8 out of 5 average rating, 976 reviews

Flat in Dedham

Hidden Gem Near Boston w/ 2 bedrooms HighSpeedWifi

Our place is close to LegacyPlace w/ shopping, restaurant, cinema, bowling, whole foods. Less than 10 minutes to Trillium Brewing. 4-5 minutes walk to Train Station, around 20 min commute to Boston. Separate entrance, living room, big play room, full bath, fully equipped kitchen. Free Washer & Dryer. High speed internet. Off street parking. Our place attracts Boston Marathon runners. Very convenient for runners to get to Boston Common shuttle bus then to the Start line of the Marathon.

5 out of 5 average rating, 240 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.

4.92 out of 5 average rating, 345 reviews

Flat in Newton

Conveniently Located Private Garden Apartment

Garden-level apartment next to a public park yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy to take in all the Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay.

4.98 out of 5 average rating, 242 reviews

Home in Dedham

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

Guest house in Framingham

4.97 out of 5 average rating, 283 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 house in West Roxbury

4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.

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Other great holiday rentals in Westwood

5 out of 5 average rating, 11 reviews

Townhouse in Norwood

Family Vacation Modern Home

HeatherRating, 5 stars2 weeks ago

Stayed at Sonnys place for a concert at Gillette with a bunch of friends. 15 mins down rt 1. Place was clean and had everything we needed. Great place with a larger group for any event in the area. Thanks again!

4.83 out of 5 average rating, 86 reviews

Home in Westwood

sweet little house

WillRating, 5 stars2 months ago

This is a cute ADU within walking distance to the Route 128 station. The unit is very spacious and reasonably priced. Wuke graciously helped us out when we needed laundry detergent. We would stay here again. Only downside is that the ADU has a bit of an unfinished feel. The shower did not have a curtain, the bedroom skylight window was papered over, and there was command-strip residue leftover in a few places.

4.89 out of 5 average rating, 76 reviews

Guest suite in Westwood

Conveniently Located & Comfy Suite - Summer's Best

LeslieRating, 5 stars3 weeks ago

I stayed here with my partner and my cousin for my sisters wedding. Everything was awesome! Steve is very responsive and was direct and clear on anything we had questions about. The listing is for the bottom floor of the house with a very spacious living room/kitchen area. The bed was so comfortable! We were surprised we couldn’t open the doors to the outside but it’s not the end of the world lol. Amazingly beautiful neighborhood, I greatly recommend if you’re in the area and don’t want to stay at a hotel!

4.95 out of 5 average rating, 44 reviews

Home in Norwood

the house of id; vintage shop, accessible space

JasonRating, 5 stars1 week ago

Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!

4.79 out of 5 average rating, 61 reviews

Flat in Norwood

The Plant Haus

MagdalyneRating, 5 stars1 week ago

This was our second time staying in Quontay’s home, and, like the first time, we loved our stay! Her home is beautiful and clean, with beautiful plants and paintings everywhere. The vibes are immaculate. It was the perfect place to stay for our night out in Canton. We highly recommend!!

4.95 out of 5 average rating, 41 reviews

Home in Norwood

The Cozy Colonial - 4 BDRM house with parking

JoanneRating, 5 stars1 month ago

This was a lovely home, and Austin did a great job making us feel welcome and answering any questions immediately. The house had everything we needed for a week’s stay. Air conditioning worked really well and especially appreciated as it was hot for a few days. Location is great, walkable to town with great restaurants and a fantastic antique market nearby. Would definitely come back!

4.94 out of 5 average rating, 16 reviews

Guest house in Norwood

Spacious Suite 15 mi from Boston

VanessaRating, 5 stars1 month ago

Mia’s place looks better than the pictures, very clean, communication was nice and smooth. Check out time is 10am instead of the 11am the app stills shows but she communicates everything in a time matter