Vacation rentals in Westwood

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Westwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Sharon

4.97 out of 5 average rating, 143 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.

Mar 29 – Apr 5

G$36,230 GYD per night

Guest favorite

Guest suite in Wellesley

4.98 out of 5 average rating, 211 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.

Feb 8 – 15

G$31,818 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

Jul 22 – 29

G$42,951 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 30 – Feb 6

G$31,179 GYD per night

Superhost

Apartment in Dedham

4.9 out of 5 average rating, 110 reviews

Prince Charming Suite *near Boston* sleeps 4-5

As you approach this non-smoking property, you will have access to on site parking. Within a few steps, you will arrive at the front door of the building. After entering and proceeding up one flight of stairs, you will find yourself at your home away from home. This private setting is nestled among single family homes. Once inside the unit, you will notice it has been professionally decorated with brand new furniture in a contemporary style for today's modern traveler.

Aug 31 – Sep 7

G$36,788 GYD per night

Guest favorite

Home in Dedham

4.98 out of 5 average rating, 182 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.

Dec 2 – 9

G$71,809 GYD per night

Guest favorite

Guest suite in Brookline

4.87 out of 5 average rating, 183 reviews

Brookline Home with a Garden

Our home is located in a peaceful neighborhood in South Brookline (Chestnut Hill), and is 5 miles from the city of Boston (about a 15 minute drive). The nearest MBTA train stop (the orange line) is about a 5 minute drive from our home. The 1 bedroom apartment is in the basement of our single family home. It is equipped with its own entrance, bathroom, kitchenette, porch, and garden. The apartment has space for up to 3 guests.

Aug 12 – 19

G$30,702 GYD per night

Guest favorite

Apartment in Randolph

4.88 out of 5 average rating, 283 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

Oct 1 – 8

G$27,414 GYD per night

Guest favorite

Guesthouse in Framingham

4.97 out of 5 average rating, 199 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.

Nov 6 – 13

G$23,106 GYD per night

Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 331 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.

Sep 19 – 26

G$26,510 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.

Dec 7 – 14

G$30,989 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.

Apr 24 – May 1

G$30,032 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 Stoughton

4.99 out of 5 average rating, 158 reviews

Modern private studio with outdoor hot tub!

Aug 7 – 14

G$58,931 GYD per night

Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 102 reviews

Warm and cozy 1st flr sweet guest suite w parking

Mar 30 – Apr 6

G$21,025 GYD per night

Guest favorite

Apartment in Newton

4.91 out of 5 average rating, 265 reviews

Conveniently Located Private Garden Apartment

Jun 9 – 16

G$34,439 GYD per night

Guest favorite

Guest suite in Sherborn

4.97 out of 5 average rating, 239 reviews

Entire Historic Carriage House with Fireplace & AC

Jul 8 – 15

G$40,926 GYD per night

Guest favorite

Apartment in Newton

4.95 out of 5 average rating, 147 reviews

Sunny, private, comfortable 1 bedroom-convenient.

Jan 5 – 12

G$32,470 GYD per night

Guest favorite

Guest suite in Newton

4.97 out of 5 average rating, 555 reviews

Spacious suite with private entrance, parking spot

Oct 3 – 10

G$27,866 GYD per night

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 264 reviews

Private 1BR Pied-a-terre

Nov 27 – Dec 4

G$19,920 GYD per night

Guest favorite

Apartment in Holliston

4.95 out of 5 average rating, 110 reviews

Lake Link

Oct 14 – 21

G$32,802 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 apartment rentals in Westwood have a kitchen?
Absolutely! We offer over 10 apartment 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 260 vacation rentals in East Dedham, over 260 vacation rentals in Ashcroft, and over 290 vacation rentals in Greenlodge.
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 Apartment Rentals in Westwood?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, 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 apartment rentals in Westwood have free parking?
Absolutely! We offer over 10 apartment 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 Stoughton

Guest suite in Winchester

Apartment in Newton

Guest suite in Sherborn

Apartment in Newton

Guest suite in Newton

Guest suite in Watertown

Apartment in Holliston

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 apartment 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 Apartment Rentals in Westwood?

Are there pet-friendly vacation rentals in Westwood?

Do apartment rentals in Westwood have free parking?

Destinations to explore