Family-friendly holiday rentals in Westwood

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Top-rated family-friendly rentals in Westwood

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Framingham

4.92 out of 5 average rating, 259 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

22–29 Jan

$325 NZD per night

Guest favourite

Guest suite in Boston

4.96 out of 5 average rating, 203 reviews

Upscale 2 Bdrm Suite: Kitchen, Spa Bath, Laundry

The home is a short 7 minute walk to Ashmont T Stop. A truly unique master bedroom and a cozy 2nd bedroom both adjacent to a marble spa bathroom (which has a heated floor and a large shower with a built in bench). With a clean, glass-tiled kitchen with granite-top counters, you'll be staying in a nice deluxe suite that is set in a friendly, safe neighborhood perfect for romantic couples, solo adventurers, and savvy business travelers who want the feel of a downtown hotel without the high price.

11–18 Jan

$281 NZD per night

Guest favourite

Home in Framingham

4.96 out of 5 average rating, 130 reviews

2BR—Charming 1900s Home—1st Floor—25min to Boston

Welcome to our Charming 1900s House! 1st Floor 1200sqft Private Rental @ our 3 Rental Property Sleeps 4 Adults/2 Children Features: Kitchen w/ Dishwasher + Essentials & Cookware Bathroom w/ Tub & Shower 2 Queen Bedrooms w/ Memory Foam Mattresses 1 Queen Memory Foam Sofa-Bed 3 Desks & Chairs Private Entrance Driveway Parking Laundry Room in Basement 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Playground/Park/Tennis Cleaned & Sanitized / COVID Conscious

6–13 May

$293 NZD per night

Superhost

Apartment in Newton

4.85 out of 5 average rating, 124 reviews

Entire Apartment in Newton, Close to Boston!

Come stay in this comfortable one bedroom apartment with large open space living room, kitchen area, bathroom, Wi-Fi, parking, and a private entrance onto a gorgeous backyard garden. Centrally located in a quiet neighborhood equidistant from Moody St. in Waltham and West Newton Sq. -- a 15 minute walk from excellent restaurants and an independent movie theater in both directions. Two dance studios with regular weekend dances nearby. To protect guests with allergies, no pets allowed.

12–19 Oct

$268 NZD per night

Guest favourite

Guest suite in Sherborn

4.98 out of 5 average rating, 241 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!

7–14 Jul

$454 NZD per night

Guest favourite

Guest suite in Littleton

4.91 out of 5 average rating, 315 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

1–8 Jul

$212 NZD per night

Guest favourite

Home in Newton

4.95 out of 5 average rating, 175 reviews

Modern, warm & inviting home!

Looking for a place to gather family for a week away or need a short term corporate rental? Great spot whether you need a place to stay while in town for a wedding, sporting event, visit w/ relatives or friends, or business. Bring the whole family and explore Boston and surrounding areas while here! Brand new construction 5 bedroom home recently furnished to suit your needs. Centrally located with access to public transportation for those looking to explore!

5–12 Jan

$1,058 NZD per night

Guest favourite

Apartment in Holliston

4.95 out of 5 average rating, 110 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

9–16 Dec

$299 NZD per night

Guest favourite

Apartment in Hudson

4.85 out of 5 average rating, 293 reviews

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.

30 Dec – 6 Jan

$183 NZD per night

Guest favourite

Cottage in Norfolk

4.96 out of 5 average rating, 106 reviews

Pondview Cottage - An inspiring retreat

Captivating, clean, bright and colorful- this modest 1 bedroom cottage welcomes you. Norfolk is a southwestern suburb of Boston and Pondview Cottage is not recommended for those looking for a convenient city location. However, we are 15 minutes from Gillette Stadium in Foxboro and yet a world away with stunning pond views. Guests with well- behaved dogs are welcome to book. A pet fee of $15/ dog/night is charged. (2 dog maximum).

25 Jul – 1 Aug

$468 NZD per night

Guest favourite

Apartment in Concord

4.94 out of 5 average rating, 207 reviews

Bishop Suite - Private suite in historic Concord

I live in historic Concord, Massachusetts, 4 miles from Concord Academy, Fenn School, Middlesex School, and many historical sites, and less than 30 miles from downtown Boston. About 4 miles from the commuter rail (train) to downtown Boston, and 2 miles to restaurants, grocery, and any kind of store you would need. For guests staying over 2 weeks, discounts can be negotiated, and an additional $75 cleaning fee will be assessed.

3–10 Mar

$226 NZD per night

Guest favourite

Apartment in Randolph

4.88 out of 5 average rating, 285 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

19–26 Apr

$249 NZD per night