Fenway–Kenmore holiday homes

We found 477 holiday rentals — enter your dates for availability

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November 2025

December 2025

Discover a selection of 96 apartments and other holiday rentals in Fenway–Kenmore that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. At the end of the day, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Fenway–Kenmore

Showing deals for:6 Feb - 13 Feb

Exceptional

(9 reviews)

Stunning apartment in Fenway

Boston, MA

11% off

for 7 nights, 1 apartment

NZ$869 per night

includes taxes & fees

Exceptional

(71 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston, MA

8% off

for 7 nights, 1 home

NZ$2,169 per night

includes taxes & fees

One of our many options travelers voted most loved! Fort Hill Inn, Boston

Wonderful

(9 reviews)

Uber Cool! Modern City Triplex +Close to center

Boston, MA

8% off

for 7 nights, 1 apartment

NZ$1,200 per night

includes taxes & fees

Exceptional

(5 reviews)

Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center

Boston, MA

8% off

for 7 nights, 1 apartment

NZ$616 per night

includes taxes & fees

Exceptional

(83 reviews)

Fresh Modern City Loft Apt! Easy Access to the city!

Boston, MA

8% off

for 7 nights, 1 apartment

NZ$361 per night

includes taxes & fees

Exceptional

(75 reviews)

Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center

Boston, MA

8% off

for 7 nights, 1 apartment

NZ$383 per night

includes taxes & fees

Exceptional

(83 reviews)

Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!

Boston, MA

8% off

for 7 nights, 1 apartment

NZ$365 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Fenway–Kenmore

Fenway Park

Find the best place to stay - Fenway–Kenmore

Showing deals for: 1 Feb - 4 Feb

Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay

Sleeps 2 · 1 bedroom

for 3 nights, 1 room

NZ$354 per night

includes taxes & fees

Premier Host

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Sleeps 14 · 7 bedrooms · 3+ bathrooms

for 3 nights, 1 home

NZ$2,503 per night

includes taxes & fees

Walk to the Bay! Ships, Dining & Cambridge Minutes Away (KING BED,POOL)

Sleeps 20 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

NZ$2,324 per night

includes taxes & fees

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Fenway–Kenmore?

Apartments are the most popular style of holiday home in Fenway–Kenmore, according to our data. Even if you have a different idea in mind, Bookabach has holiday homes in all shapes and sizes. Browse our options to find your ideal fit.

How much does it cost to rent a holiday home in Fenway–Kenmore?

A number of factors can influence what you'll pay for your holiday home in Fenway–Kenmore, including the length of stay, season and type of property. However, all our holiday homes have something in common — unbeatable value. Simply enter your travel dates to find your perfect match.

How much does it cost to rent a beach house in Fenway–Kenmore?

When you travel and the size and style of the property will influence the cost of your beachside stay. Type in your Fenway–Kenmore travel dates to view your available options on Bookabach. Can't live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want in your beach house.

Are there pet-friendly holiday homes in Fenway–Kenmore?

Yes, there are. You can choose from 58 holiday homes that cater to pets in Fenway–Kenmore. Many of our pet-friendly holiday homes even have an area outdoors for your fur child to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect holiday home on Bookabach.

Can I rent a house with a pool in Fenway–Kenmore?

Grab your swimsuit and inflatable swan, because there are 13 houses with a private pool in Fenway–Kenmore. Base yourself at one of these superb holiday homes and every day will be a pool day. Simply enter your travel dates into Bookabach, then use the "pool" filter to find the ideal place for a splashing good time!

What are popular home amenities in Fenway–Kenmore?

When it comes to home amenities that guests are looking for in Fenway–Kenmore, a nearby river, a swimming pool and a water view rank the highest. With Bookabach holiday homes, you'll have options to suit your taste and style, whether you're travelling with relatives, friends or even pets.

Are there large group holiday homes in Fenway–Kenmore?

With five Fenway–Kenmore holiday properties that can host five or more people, you can invite a few extra buddies or family members along. Whether you're planning a casual gathering or a special event, Bookabach will help you book a comfortable space to match the occasion.

Are there holiday homes in Fenway–Kenmore that welcome kids?

Fenway–Kenmore has 58 family-friendly holiday homes to choose from. And finding a stay that welcomes kids is a breeze with Bookabach's "Properties good for families" filter. On top of having the entire place to yourselves, you'll also get perks and amenities like dining rooms, kitchens and private pools.

What are the top attractions for families in Fenway–Kenmore?

Keeping the kids occupied during your stay in Fenway–Kenmore is child's play with these fabulous family-friendly attractions:

New England Aquarium
Museum of Science
Boston Tea Party Ship

Are there one-bedroom holiday homes in Fenway–Kenmore?

Yes, you can take your pick from 18 one-bedroom homes in Fenway–Kenmore. Whether you want a townhouse or an upmarket condo, our one-bedroom properties are ideal if you don't require tons of space. One of the major perks of having your own pad? You won't have to share your getaway with strangers.

Can I find two-bedroom holiday homes in Fenway–Kenmore?

Take off with your besties and experience complete comfort and privacy in one of the 20 two-bedroom holiday homes Fenway–Kenmore has to offer.

Are there holiday homes with WiFi in Fenway–Kenmore?

Choose from five holiday homes with WiFi in Fenway–Kenmore. If you want to disconnect from daily life on your break, but still want to be connected to the web, these properties have what you need. Narrow your search by applying the WiFi filter on Bookabach.

How can I find holiday homes with air conditioning in Fenway–Kenmore?

There are 58 Bookabach holiday homes with air conditioning in Fenway–Kenmore giving you that gentle, cool breeze and extra element of comfort. Enter your desired travel dates and then use our handy filter tool to find stays with air conditioning.

How old do you have to be to rent a holiday home in Fenway–Kenmore?

Age restrictions can differ between properties on Bookabach, so look at the rules of the holiday home in Fenway–Kenmore you're considering. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Fenway–Kenmore for?

How long you can book a holiday home in Fenway–Kenmore is up to the property. Simply enter your selected travel dates to view a list of options offering extended stays. With many creature comforts such as washing machines and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Fenway–Kenmore.