Whitman Holiday Rentals

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Our top choices for Whitman holiday rentals

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave
2.0 star property
South End
7.4 out of 10, Good, (133)
"Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small."
United Kingdom
Fanny Pei Yee
Maverick Suites at 400 Columbus Ave

Maverick Suites at 402 Columbus Ave

Maverick Suites at 402 Columbus Ave
2.5 star property
South End
7.8 out of 10, Good, (68)
"Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. "
United States
Isaiah Joel Santa
Maverick Suites at 402 Columbus Ave

The Chester Hotel

The Chester Hotel
4.0 star property
South End
8.6 out of 10, Excellent, (28)
"The property was spacious and clean. We enjoyed our stay!"
United States
Bryan
The price is AU$538
includes taxes & fees
14 Dec - 15 Dec
The Chester Hotel

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
South Boston
9.8 out of 10, Exceptional, (182)
"Great home with everything you need for an awesome stay. "
United States
Lisa B.
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Modern 2 BR, 1BA Near Convention Center & Seaport

Modern 2 BR, 1BA Near Convention Center & Seaport
South Boston
9.8 out of 10, Exceptional, (201)
"The apartment and location were excellent. We loved how convenient it was to access all the attractions."
United States
Monica B.
Modern 2 BR, 1BA Near Convention Center & Seaport

Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!
Hyde Park
9.6 out of 10, Exceptional, (24)
"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."
United States
TIARA V.
The price is AU$588
includes taxes & fees
17 Dec - 18 Dec
Hidden Gem right in the city of Boston!

Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston

Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston
South End
3.4 out of 10, (3)
"We arrived and were informed by property management that the host did not have the right under their lease to rent out the property on Vrbo. We were made to leave and find alternate arrangements last minute for my son’s graduation weekend. Once I informed the host they stopped responding. Now fighting to get refund of nearly 3k. Beyond a disappointment (and didn’t help that it was pouring down rain)"
United States
Lori S.
The price is AU$1,087
includes taxes & fees
7 Jan - 8 Jan 2026
Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston

Thomas Sea Suites

Thomas Sea Suites
3.5 star property
Plymouth Downtown Waterfront District
9.0 out of 10, Wonderful, (97)
"Great room & views"
United States
Al
Thomas Sea Suites

Excellent 2 bedroom condo in South Boston

Excellent 2 bedroom condo in South Boston
South Boston
10.0 out of 10, Exceptional, (36)
"The host was great, and very responsive to any and all questions I had about the property. It is in a great location, an easy walk to the T. The apartment was very comfortable and worked perfect for our getaway."
United States
Nancy Y.
Excellent 2 bedroom condo in South Boston

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train
Hyde Park
10.0 out of 10, Exceptional, (17)
"Lots of thoughtful touches, enjoyable spot for us to land while visiting Boston."
United States
Wendy K.
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal

West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal
West Roxbury
9.8 out of 10, Exceptional, (81)
"Nice property in a nice location. It worked really well for our weekend trip."
United States
Deborah M.
West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal

Modern 2br with W/D in unit, Parking, central air

Modern 2br with W/D in unit, Parking, central air
Roslindale
10.0 out of 10, Exceptional, (62)
"Lots of room and great location! Wonderful stay!"
United States
Amy C.
Modern 2br with W/D in unit, Parking, central air

Lovely 3 bedroom 2 bath “6 miles from downtown”

Lovely 3 bedroom 2 bath “6 miles from downtown”
Dorchester
8.2 out of 10, Very good, (10)
"The host was very responsive and the unit has everything you can think of to feel comfortable for your stay. Clean and very beautiful home. 10/10 experience I would highly recommend and book this unit again."
United States
Vey B.
Lovely 3 bedroom 2 bath “6 miles from downtown”

Beautiful studio in historic neighborhood of Boston. Super close to downtown!

Beautiful studio in historic neighborhood of Boston. Super close to downtown!
Roxbury
9.8 out of 10, Exceptional, (45)
"I loved the location. It was convenient to everything I wanted to do. Madhouse Cafe being in walking distance was a phenomenal find."
United States
Marsha G.
Beautiful studio in historic neighborhood of Boston. Super close to downtown!

Ocean Dreams, Waves as far as the eyes can see...........

Ocean Dreams, Waves as far as the eyes can see...........
Scituate
9.8 out of 10, Exceptional, (156)
"Beautiful beach house with everything we needed and the location can’t be beat. Hope to stay again the next time I’m looking for ocean views and beach time!"
United States
Elise T.
The price is AU$1,027
includes taxes & fees
26 Dec - 27 Dec
Ocean Dreams, Waves as far as the eyes can see...........

14b-Charming, beautiful 3-bedroom apartment in Boston

14b-Charming, beautiful 3-bedroom apartment in Boston
2.0 star property
Dorchester
10.0 out of 10, Exceptional, (15)
"Clean, cozy. 5star review from us. Very responsive when messaging. Would recommend and will come back if we’re in the area. "
United States
Vision T.
The price is AU$658
includes taxes & fees
14 Dec - 15 Dec
14b-Charming, beautiful 3-bedroom apartment in Boston

The Heart of Southie (Garage + Roof Deck)

The Heart of Southie (Garage + Roof Deck)
South Boston
10.0 out of 10, Exceptional, (46)
"We had a great stay!"
United States
Rachel H.
The Heart of Southie (Garage + Roof Deck)

Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T
Roxbury
9.4 out of 10, Exceptional, (19)
"Had a perfect stay! The place was wonderful and worked out for what we needed. Thank you!"
United States
Renee G.
Clean, Contemporary Escape | Near T

Cozy, Adorable 1-bedroom apartment - in tourist area. Sleeps 4

Cozy, Adorable 1-bedroom apartment - in tourist area. Sleeps 4
South End
9.8 out of 10, Exceptional, (58)
"Beautiful home, amazing location. We come to visit Boston often with our dog and this has been our favorite place so far. We cant wait to come back!"
United States
paige w.
Cozy, Adorable 1-bedroom apartment - in tourist area. Sleeps 4

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston

76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Dorchester
10.0 out of 10, Exceptional, (11)
"We loved this home. It was clean, well equipped and very well located for our family of 8 to visit Boston. Had a great time and loved the house. "
United States
Arlene P.
The price is AU$817
includes taxes & fees
15 Dec - 16 Dec
76/2-SPRING GETAWAY EARLY BIRD 10%!Cozy & Spacious 5-bedroom apartment in Boston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Whitman Hotel Reviews

Find out more about Whitman

Everything you need to know about Whitman holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Whitman holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Whitman holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Whitman holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Whitman. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Whitman holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Whitman holiday rentals we have selected for you start as low as AU$538 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Whitman rentals

At Expedia, we put the best Whitman holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Whitman rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Whitman holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Whitman. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Whitman?

Yes, there are holiday rentals close to the most popular sights in Whitman, or you can select a more secluded option if you're looking for a relaxing stay. Whitman is known for its shopping and restaurants. Make sure you have time to check out the beaches while you're in the area.

What are some of the best holiday rentals that Whitman has to offer?

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi: This holiday home rental outside of Whitman is located in the city centre, and offers a balcony, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Whitman?

While exploring the area, visit family-friendly sights like Rockland Ice Rink, or get outside and enjoy nature at Hobart Pond. Other places in town to visit include Whitman Townhall and Whitman Public Library.

What’s a holiday rental in Whitman like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Whitman. Holiday rentals offer extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family trip.