Boston Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Boston holiday rentals

Exterior detail

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville

QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (136 reviews)
"Perfect place to stay, clean, close to everything, Would stay again and highly recommend!"
United States
Molly S.
The price is HK$1,323
HK$2,772 total
includes taxes & fees
23 Apr - 24 Apr
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
Exterior

Treehouse views in Historic Downtown Thomasville, Georgia

Treehouse views in Historic Downtown Thomasville, Georgia
Thomasville
10.0 out of 10, Exceptional, (9 reviews)
"Walking to downtown was great! The house is large and clean, and we hope to stay there again!"
United States
Catherine C.
The price is HK$1,551
HK$2,975 total
includes taxes & fees
22 Apr - 23 Apr
Treehouse views in Historic Downtown Thomasville, Georgia
Interior

The Mash Manor

The Mash Manor
Dawson Street Historic District
9.2 out of 10, Wonderful, (28 reviews)
"Perfect place for our group of 5! Everyone had their own bedroom and bath and the house was spacious and just beautiful! We loved the quick walk to downtown Thomasville and all the holiday festivities. The owner was very responsive and helpful as well. "
United States
Debra B.
The price is HK$2,361
HK$5,301 total
includes taxes & fees
22 Apr - 23 Apr
The Mash Manor
Exterior detail

SOUTHERN CHARM (Kid’s Bunk Room!)

SOUTHERN CHARM (Kid’s Bunk Room!)
Thomasville
10.0 out of 10, Exceptional, (84 reviews)
"Wonderful stay would love to stay again!"
United States
Lakeisa C.
The price is HK$1,292
HK$2,736 total
includes taxes & fees
23 Apr - 24 Apr
SOUTHERN CHARM (Kid’s Bunk Room!)
2 bedrooms, iron/ironing board, travel cot, WiFi

Charming 2-bedroom cottage built with children and pets in mind.

Charming 2-bedroom cottage built with children and pets in mind.
Thomasville
9.6 out of 10, Exceptional, (10 reviews)
"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 HK$937
HK$2,292 total
includes taxes & fees
22 Apr - 23 Apr
Charming 2-bedroom cottage built with children and pets in mind.
Exterior

The Budd-Pafford House - The Exploration Suite

The Budd-Pafford House - The Exploration Suite
Monticello
8.8 out of 10, Excellent, (11 reviews)
"Beautiful, clean home. Well stocked kitchen and bedroom/bathroom. My bed was wonderful. The house is within walking distance to many restaurants, shops, markets, etc. Wonderful location."
United States
Jennifer T.
The price is HK$1,175
HK$1,879 total
includes taxes & fees
22 Apr - 23 Apr
The Budd-Pafford House - The Exploration Suite
Fridge, microwave, oven, stovetop

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (56 reviews)
"Enjoyed our stay very much."
United States
Barbara F.
The price is HK$744
HK$2,401 total
includes taxes & fees
27 Apr - 28 Apr
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Interior

Camellia Cottage - wheelchair friendly

Camellia Cottage - wheelchair friendly
Monticello
9.8 out of 10, Exceptional, (16 reviews)
"Great location, clean, and comfortable. "
United States
Teresa
The price is HK$916
HK$1,893 total
includes taxes & fees
27 Apr - 28 Apr
Camellia Cottage - wheelchair friendly
Fridge, microwave, oven, stovetop

Newly Built, Stunning 4BR/2BA with Waterfront Views

Newly Built, Stunning 4BR/2BA with Waterfront Views
Thomasville
9.8 out of 10, Exceptional, (16 reviews)
"Great place to stay and good people to deal with. "
United States
RYAN H.
The price is HK$1,104
HK$3,166 total
includes taxes & fees
26 Apr - 27 Apr
Newly Built, Stunning 4BR/2BA with Waterfront Views
Dining

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Thomasville
10.0 out of 10, Exceptional, (16 reviews)
"Very beautiful property and well maintained with southern charm. "
United States
Rebecca N.
The price is HK$1,323
HK$3,007 total
includes taxes & fees
27 Apr - 28 Apr
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Fridge, microwave, oven, stovetop

Modern Home Near Downtown Thomasville

Modern Home Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (30 reviews)
"House was beautiful, comfortable, amenities were good. "
United States
Elizabeth C.
The price is HK$783
HK$2,756 total
includes taxes & fees
22 Apr - 23 Apr
Modern Home Near Downtown Thomasville
Terrace/patio

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
Thomasville
9.8 out of 10, Exceptional, (8 reviews)
"Nicely equipped kitchen , great areas to relax and very quiet "
United States
Jesse V.
The price is HK$2,036
HK$5,112 total
includes taxes & fees
22 Apr - 23 Apr
Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks
Fridge, microwave, oven, stovetop

Southern Charm Home: Pool + Fireplace + Large Yard

Southern Charm Home: Pool + Fireplace + Large Yard
Thomasville
10.0 out of 10, Exceptional, (2 reviews)
"Convenient location and has everything you need."
United States
Dee J.
The price is HK$1,253
HK$3,303 total
includes taxes & fees
26 Apr - 27 Apr
Southern Charm Home: Pool + Fireplace + Large Yard
Interior

Dog friendly nature preserve Monticello, FL

Dog friendly nature preserve Monticello, FL
Monticello
10.0 out of 10, Exceptional, (1 review)
"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 HK$1,370
HK$1,695 total
includes taxes & fees
30 Apr - 1 May
Dog friendly nature preserve Monticello, FL
Outdoor dining

An elegant waterside retreat in the Red Hills

An elegant waterside retreat in the Red Hills
Thomasville
9.8 out of 10, Exceptional, (26 reviews)
"Was absolutely amazing we will be comin back for sure!!! So peaceful just perfect "
United States
brittiny c.
The price is HK$744
HK$2,424 total
includes taxes & fees
26 Apr - 27 Apr
An elegant waterside retreat in the Red Hills
2 bedrooms, iron/ironing board, WiFi, bed sheets

Mimosa Cottage - Near Downtown Thomasville

Mimosa Cottage - Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (18 reviews)
"Nice and clean great location "
United States
Russ W.
The price is HK$705
HK$2,445 total
includes taxes & fees
5 May - 6 May
Mimosa Cottage - Near Downtown Thomasville
Fridge, microwave, oven, stovetop

Mimosa Getaway - Less than 1 mile from Downtown

Mimosa Getaway - Less than 1 mile from Downtown
Thomasville
9.6 out of 10, Exceptional, (13 reviews)
"Clean, convenient location, and easy check in."
United States
Emily H.
The price is HK$783
HK$2,522 total
includes taxes & fees
22 Apr - 23 Apr
Mimosa Getaway - Less than 1 mile from Downtown
Fridge, microwave, oven, stovetop

Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.

Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
Monticello
10.0 out of 10, Exceptional, (21 reviews)
"Clean great location and very friendly thank you for the stay we will be back"
United States
ROBERT B.
The price is HK$1,096
HK$2,486 total
includes taxes & fees
22 Apr - 23 Apr
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
TV, books

Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.6 out of 10, Exceptional, (17 reviews)
"The Place was very comfortable and clean. "
United States
David Y.
The price is HK$955
HK$2,966 total
includes taxes & fees
27 Apr - 28 Apr
Sprawling Updated Ranch with Fireplace on Wimbledon
Fridge, microwave, oven, stovetop

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage

Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
Thomasville
9.6 out of 10, Exceptional, (10 reviews)
"Great place"
United States
Michael S.
The price is HK$783
HK$2,780 total
includes taxes & fees
26 Apr - 27 Apr
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
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

Baymont by Wyndham Thomasville

Baymont by Wyndham Thomasville

8/10 Good
"I stayed one night at this hotel to rest up for the Rose City Run. It wasn't in the best of conditions; the stairway to the second floor wasn't well lit at night, and there was chipped paint on the railings. But at least my room was reasonably clean, and my bed was comfortable, so I still had a good night's sleep."
Scott 1-night trip
Posted 6 hours ago
Baymont by Wyndham Thomasville

Find out more about Boston

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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?

Orchard Pines - 4 Bed, 3.5 Bath Private Thomasville Retreat on Pond + Kayaks: This holiday home rental outside of Boston is located on the waterfront, and has a patio, a selection of games and a BBQ to put you at ease 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 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.