Boston Holiday Rentals

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Holiday Rentals in Boston

Charming 2-bedroom cottage built with children and pets in mind.
2.0 star property
9.6 out of 10, Exceptional, (4)
"We enjoyed our stay in Thomasville! The beds were comfortable, everything was clean and my dogs especially loved the court yard area. It was in walking distance to downtown which we loved. Would definitely stay here again! "
United States
Lindsey J.
The price is NZ$483
includes taxes & fees
2 Dec - 3 Dec
Charming 2-bedroom cottage built with children and pets in mind.
Cottage 229 - Downtown Historic Thomasville Getaway
2.0 star property
10.0 out of 10, Exceptional, (8)
"This home was wonderful and steps to down town. The rooms are very comfortable with great mattresses and bedding. The outdoor covered patio was perfect for a small dinner, and watching the birds and squirrels in the back yard. We took a morning stroll around the historical neighborhood to enjoy the beautiful homes. We will be back for sure. "
United States
Lori B.
The price is NZ$717
includes taxes & fees
1 Dec - 2 Dec
Cottage 229 - Downtown Historic Thomasville Getaway
Mimosa Getaway - Less than 1 mile from Downtown
2.0 star property
9.4 out of 10, Exceptional, (9)
"Great place to stay , clean, kids loved the bunk beds, much better than a hotel, enjoyed it"
United States
carl e.
The price is NZ$566
includes taxes & fees
4 Nov - 5 Nov
Mimosa Getaway - Less than 1 mile from Downtown
Camellia Cottage - wheelchair friendly
10.0 out of 10, Exceptional, (6)
"Great location, clean, and comfortable. "
United States
Teresa
The price is NZ$316
includes taxes & fees
4 Nov - 5 Nov
Camellia Cottage - wheelchair friendly
Sprawling Updated Ranch with Fireplace on Wimbledon
2.0 star property
9.4 out of 10, Exceptional, (9)
"The house was very clean and up to date! Really enjoyed the stay!"
United States
Sondra A.
The price is NZ$587
includes taxes & fees
4 Nov - 5 Nov
Sprawling Updated Ranch with Fireplace on Wimbledon
Dog friendly nature preserve Monticello, FL
10.0 out of 10, Exceptional, (1)
"Quiet and relaxing spot. Very well maintained and clean. Wonderful hosts. My only regret is that we couldn't stay longer."
United States
KARL L.
The price is NZ$371
includes taxes & fees
29 Nov - 30 Nov
Dog friendly nature preserve Monticello, FL
Treehouse views in Historic Downtown Thomasville, Georgia
10.0 out of 10, Exceptional, (1)
"Great location near downtown. I chose this spot because of the nice check in,/ check out times (3 & 11). Recommend!"
United States
Michael B.
The price is NZ$626
includes taxes & fees
9 Nov - 10 Nov
Treehouse views in Historic Downtown Thomasville, Georgia
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
10.0 out of 10, Exceptional, (126)
"This bungalow is located conveniently to everything. It was comfortable and quiet. The hostess was extremely friendly and helpful. A definite A for a visit to Thomasville."
United States
Kurt G.
The price is NZ$619
includes taxes & fees
4 Nov - 5 Nov
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
SOUTHERN CHARM (Kid’s Bunk Room!)
10.0 out of 10, Exceptional, (73)
"Property was very clean and cool! "
United States
Carlyn B.
The price is NZ$605
includes taxes & fees
4 Nov - 5 Nov
SOUTHERN CHARM (Kid’s Bunk Room!)
Modern Home Near Downtown Thomasville
10.0 out of 10, Exceptional, (26)
"We had a delightful stay at this lovely home in Thomasville, GA! The house was clean, comfortable, and beautifully maintained, with everything we needed for a relaxing family getaway. The quiet neighborhood and charming local touches made it feel like a true home away from home. We truly appreciated the thoughtful hospitality and would gladly stay here again!"
United States
Frederick C.
The price is NZ$573
includes taxes & fees
17 Nov - 18 Nov
Modern Home Near Downtown Thomasville
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
10.0 out of 10, Exceptional, (51)
"Stayed here for my son’s graduation from FSU and it worked out well. "
United States
Jana H.
The price is NZ$536
includes taxes & fees
9 Nov - 10 Nov
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Cozy studio in a vintage 1930’s Gulf Gas Station in charming Thomasville GA
10.0 out of 10, Exceptional, (2)
"Loved this adorable place! Very tastefully appointed - bed and sofa were extremely comfy. It’s super convenient to all the restaurants and shops in the downtown area (“the bricks”). Super clean. Really nice finish work in the interior - gorgeous high wood paneled ceilings, nice crisp mill work and great shower!"
United States
Sallie C.
The price is NZ$314
includes taxes & fees
16 Nov - 17 Nov
Cozy studio in a vintage 1930’s Gulf Gas Station in charming Thomasville GA
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.
10.0 out of 10, Exceptional, (3)
"The place was clean and beautiful! I felt safe there, thank you!"
United States
Sabrina S.
The price is NZ$432
includes taxes & fees
4 Nov - 5 Nov
2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
10.0 out of 10, Exceptional, (15)
"One of the best vacation rentals I have ever had the pleasure of renting."
United States
C B.
The price is NZ$569
includes taxes & fees
16 Nov - 17 Nov
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
9.8 out of 10, Exceptional, (7)
"Great place"
United States
Michael S.
The price is NZ$615
includes taxes & fees
4 Nov - 5 Nov
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Mimosa Cottage - Near Downtown Thomasville
9.8 out of 10, Exceptional, (9)
"Booked for my husband’s business trip. The house had all the niceties. Very confortable stay. Would book again. "
United States
evelyn r.
The price is NZ$505
includes taxes & fees
4 Nov - 5 Nov
Mimosa Cottage - Near Downtown Thomasville
The Roost - Downtown Thomasville
10.0 out of 10, Exceptional, (14)
"Everything was great!"
United States
Liz S.
The price is NZ$470
includes taxes & fees
4 Nov - 5 Nov
The Roost - Downtown Thomasville
An elegant waterside retreat in the Red Hills
9.8 out of 10, Exceptional, (23)
"This property provided a well needed time of relaxation with a great view of God's magnificent nature!"
United States
Angie E.
The price is NZ$513
includes taxes & fees
4 Nov - 5 Nov
An elegant waterside retreat in the Red Hills
Newly Built, Stunning 4BR/2BA with Waterfront Views
10.0 out of 10, Exceptional, (12)
"Great location!!Great home!!"
United States
Lee C.
The price is NZ$636
includes taxes & fees
4 Nov - 5 Nov
Newly Built, Stunning 4BR/2BA with Waterfront Views
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
10.0 out of 10, Exceptional, (5)
"Incredible host great location will he back. The was outstanding. I highly recommend this property "
United States
Russ W.
The price is NZ$785
includes taxes & fees
4 Nov - 5 Nov
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
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 Boston Hotel Reviews

Find out more about Boston

Everything you need to know about Boston 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 Boston 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 Boston holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Boston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Boston. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Boston 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 Boston holiday rentals we have selected for you start as low as NZ$314 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Boston rentals

At Expedia, we put the best Boston 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 Boston 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 Boston 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 Boston. 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 Boston?

Yes, there are holiday rentals close to the most popular sights in Boston, or you can select a more secluded option if you're looking for a relaxing stay.

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

2-bedroom house in charming Thomasville w/ small, fenced area & covered parking.: This holiday home rental outside of Boston has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Boston?

Explore the area and family-friendly sights such as Sweet Grass Dairy Marketplace, or get out into nature at a spot like Thomasville Rose Garden. In the wider area, you’ll find Thomasville's Historic Big Oak and Pebble Hill Plantation.

What’s a holiday rental in Boston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Boston. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.