Vacation rentals in Westwood

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Top-rated vacation rentals in Westwood

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Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 106 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

Mar 22 – 29

G$21,053 GYD per night

Guest favorite

Guest suite in Sharon

4.97 out of 5 average rating, 146 reviews

Cozy Lakeview Guesthouse

This Lakeview Guesthouse is private and stunning! It has its private entrance, deck, and parking. It features 1 bedroom with a Queen Bed, TV, with a sliding door that opens to a deck. The living room has a view of the Lake and a smart TV. The bathroom includes a tub (not a jacuzzi) and sitting on bench shower. The kitchen is fully equipped with stainless steel appliances. Guests have access to the lake, via beach pass during the summer. During the winter you can skate at your own risk.

Oct 13 – 20

G$38,530 GYD per night

Guest favorite

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

May 6 – 13

G$30,520 GYD per night

Guest favorite

Guest suite in Wellesley

4.98 out of 5 average rating, 212 reviews

Spacious Private Entrance Master Bedroom/Bath

Private entrance master bedroom w/exclusive use of attached master bathroom. Studio apartment-like room w/private exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, stores, Whole Foods. Short drive to Babson. Sizable room, tasteful decor, king bed, sitting area, microwave, fridge (no TV). High-speed wifi, deck, situated amongst the treetops. Safe suburban neighborhood. Walk/jog trails, tennis courts, walk to spa/gym/yoga w/reasonable day fees.

Sep 16 – 23

G$31,861 GYD per night

Guest favorite

Apartment in Dedham

4.95 out of 5 average rating, 154 reviews

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

Sep 18 – 25

G$43,008 GYD per night

Guest favorite

Guest suite in Dover

4.98 out of 5 average rating, 182 reviews

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-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. 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, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

Jan 3 – 10

G$31,221 GYD per night

Guest favorite

Home in Dedham

4.98 out of 5 average rating, 185 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home, just 1.5 miles from Boston's transit. 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. Pets and families are warmly welcomed.

Mar 10 – 17

G$75,247 GYD per night

Guest favorite

Apartment in Randolph

4.88 out of 5 average rating, 286 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

Sep 21 – 28

G$27,451 GYD per night

Guest favorite

Guesthouse in Framingham

4.98 out of 5 average rating, 202 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.

Mar 30 – Apr 6

G$25,242 GYD per night

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 332 reviews

Scandi-Modern Apartment

Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles. EV charging available.

Oct 20 – 27

G$26,545 GYD per night

Guest favorite

Loft in Natick

4.99 out of 5 average rating, 174 reviews

Lakeside Studio Loft

Bright, open, private 900 sq foot loft space on Lake Cochituate. This is a mother-in-law suite attached to our lakeside home. This airy studio includes a queen bed, kitchen (no stove or oven) toaster,microwave,hot plate and George Foreman grill, skylit bathroom, living room with television and lakeview deck.

Apr 21 – 28

G$31,031 GYD per night

Guest favorite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 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.

Jun 24 – Jul 1

G$31,638 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Westwood vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Westwood's top sights

Legacy Place62 locals recommend

Dedham Mall5 locals recommend

Wegmans9 locals recommend

Showcase Cinema de Lux Legacy Place11 locals recommend

Legal C Bar8 locals recommend

50's Diner3 locals recommend

Other great vacation rentals in Westwood

Guest favorite

Guest suite in Weston

5.0 out of 5 average rating, 116 reviews

FLOWER FARM GETAWAY 2BR 15MIN TO BOSTON

Mar 2 – 9

G$47,521 GYD per night

Guest favorite

Cottage in Millis

4.99 out of 5 average rating, 100 reviews

Windy Knob Farm Cottage - stay on a working farm

Oct 16 – 23

G$40,548 GYD per night

Guest favorite

Guest suite in Newton

4.97 out of 5 average rating, 557 reviews

Spacious suite with private entrance, parking spot

Oct 20 – 27

G$27,811 GYD per night

Guest favorite

Apartment in Framingham

4.95 out of 5 average rating, 182 reviews

Comfortable apartment in Framingham

May 27 – Jun 3

G$21,785 GYD per night

Superhost

Apartment in Dedham

4.9 out of 5 average rating, 111 reviews

Prince Charming Suite *near Boston* sleeps 4-5

Sep 29 – Oct 6

G$36,715 GYD per night

Guest favorite

Apartment in Framingham

4.9 out of 5 average rating, 303 reviews

Apartment Floris

Nov 13 – 20

G$18,715 GYD per night

Guest favorite

Guest suite in Brookline

4.88 out of 5 average rating, 184 reviews

Brookline Home with a Garden

Oct 11 – 18

G$30,744 GYD per night

Guest favorite

Home in Quincy

4.96 out of 5 average rating, 124 reviews

Artist's Haven (2)

May 23 – 30

G$24,186 GYD per night

Show all

Quick stats about vacation rentals in Westwood

Total rentals
50 properties
Wifi availability
50 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
3K reviews

Frequently Asked Questions

Do house rentals in Westwood have wifi?
Absolutely! We offer over 30 house rentals with wifi in Westwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Westwood?
Experience the best of Westwood with our apartment rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Westwood have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Westwood. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Westwood?
Yes! Work meets play with ease at over 30 vacation rentals in Westwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Westwood have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Westwood. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Westwood?
Make yourself at home in Westwood by choosing from our most frequently booked neighborhoods. We have over 290 vacation rentals in Greenlodge, over 260 vacation rentals in East Dedham, and over 260 vacation rentals in Ashcroft.
Are there family-friendly vacation rentals in Westwood?
Westwood has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Westwood?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 30 homes with air conditioning, over 30 homes with free parking, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Westwood?
Four-legged friends are welcome in Westwood. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Westwood have free parking?
Absolutely! We offer over 30 house rentals with free parking in Westwood. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Westwood

Top-rated vacation rentals in Westwood

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Westwood vacation rentals

Stay near Westwood's top sights

Other great vacation rentals in Westwood

Guest suite in Weston

Cottage in Millis

Guest suite in Newton

Apartment in Framingham

Apartment in Dedham

Apartment in Framingham

Guest suite in Brookline

Home in Quincy

Quick stats about vacation rentals in Westwood

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Westwood have wifi?

How much does it cost to stay in apartment rentals in Westwood?

Do house rentals in Westwood have a kitchen?

Are there vacation rentals with a dedicated workspace in Westwood?

Do house rentals in Westwood have air conditioning?

Where should I stay in Westwood?

Are there family-friendly vacation rentals in Westwood?

What are the most popular amenities for House Rentals in Westwood?

Are there pet-friendly vacation rentals in Westwood?

Do house rentals in Westwood have free parking?

Destinations to explore