Boston Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Boston holiday rentals

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, (20 reviews)
"Stay and area was Great!"
United States
Geoff
The price is HK$587
HK$2,388 total
includes taxes & fees
8 Jun - 9 Jun
Mimosa Cottage - Near Downtown Thomasville
Interior

Camellia Cottage - wheelchair friendly

Camellia Cottage - wheelchair friendly
Monticello
9.6 out of 10, Exceptional, (18 reviews)
"Great location, clean, and comfortable. "
United States
Teresa
The price is HK$987
HK$1,987 total
includes taxes & fees
9 Jun - 10 Jun
Camellia Cottage - wheelchair friendly
Hair dryer, towels

Newly Renovated - Thomasville Getaway - Large Fenced Backyard

Newly Renovated - Thomasville Getaway - Large Fenced Backyard
Thomasville
10.0 out of 10, Exceptional, (58 reviews)
"Enjoyed our stay very much."
United States
Barbara F.
The price is HK$697
HK$2,423 total
includes taxes & fees
8 Jun - 9 Jun
Newly Renovated - Thomasville Getaway - Large Fenced Backyard
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, (31 reviews)
"Quiet, peaceful surroundings "
United States
Lili G.
The price is HK$653
HK$2,391 total
includes taxes & fees
5 Jul - 6 Jul
An elegant waterside retreat in the Red Hills
Interior

The Roost - Downtown Thomasville

The Roost - Downtown Thomasville
Downtown Historic District
10.0 out of 10, Exceptional, (25 reviews)
"Excellent stay!"
United States
Becky A W.
The price is HK$733
HK$2,116 total
includes taxes & fees
15 Jun - 16 Jun
The Roost - Downtown Thomasville
Terrace/patio

The Budd-Pafford House: The Rose Room

The Budd-Pafford House: The Rose Room
Monticello
8.2 out of 10, Very good, (10 reviews)
"Easy location to access. Friendly host."
United States
Mary Ellen W.
The Budd-Pafford House: The Rose Room
Fridge, microwave, oven, stovetop

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)
"Host was very responsive and accommodating. Home was comfortable and well equipped. Would book again!"
United States
Andrew K.
The price is HK$881
HK$2,219 total
includes taxes & fees
8 Jun - 9 Jun
Charming 2-bedroom cottage built with children and pets in mind.
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, (140 reviews)
"Perfect place to stay, clean, close to everything, Would stay again and highly recommend!"
United States
Molly S.
The price is HK$1,324
HK$2,734 total
includes taxes & fees
8 Jun - 9 Jun
QUAIL COTTAGE - 2 Bed home 4 blocks from downtown Thomasville
TV, books

Mimosa Stay Cottage - Thomasville Close to all the Charm

Mimosa Stay Cottage - Thomasville Close to all the Charm
Thomasville
10.0 out of 10, Exceptional, (5 reviews)
"Great location spacious layout furnished perfectly "
United States
Damian Ray V.
The price is HK$733
HK$2,500 total
includes taxes & fees
6 Jul - 7 Jul
Mimosa Stay Cottage - Thomasville Close to all the Charm
TV, books

Sprawling Updated Ranch with Fireplace on Wimbledon

Sprawling Updated Ranch with Fireplace on Wimbledon
Thomasville
9.6 out of 10, Exceptional, (20 reviews)
"Was a very comfortable home for our girl’s trip of 5 ladies! "
United States
Julia N.
The price is HK$807
HK$2,916 total
includes taxes & fees
14 Jun - 15 Jun
Sprawling Updated Ranch with Fireplace on Wimbledon
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)
"Great place, perfect for the weekend. "
United States
bill W.
The price is HK$733
HK$2,586 total
includes taxes & fees
15 Jun - 16 Jun
Mimosa Getaway - Less than 1 mile from Downtown
Fridge, microwave, oven, stovetop

Modern Home Near Downtown Thomasville

Modern Home Near Downtown Thomasville
Thomasville
10.0 out of 10, Exceptional, (31 reviews)
"House was beautiful, comfortable, amenities were good. "
United States
Elizabeth C.
Modern Home Near Downtown Thomasville
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, (18 reviews)
"The property was clean and spacious for our family. The access were very easy."
United States
Frederick E
The price is HK$909
HK$3,034 total
includes taxes & fees
15 Jun - 16 Jun
Newly Built, Stunning 4BR/2BA with Waterfront Views
Exterior

The Budd-Pafford House - The Exploration Suite

The Budd-Pafford House - The Exploration Suite
Monticello
9.0 out of 10, Wonderful, (13 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 Budd-Pafford House - The Exploration Suite
Fridge, microwave, oven, stovetop

Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville

Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
Thomasville
9.4 out of 10, Exceptional, (29 reviews)
"Very comfortable place to stay when visiting Thomasville! "
United States
Sarah S.
The price is HK$939
HK$3,027 total
includes taxes & fees
22 Jun - 23 Jun
Spacious 4BR/3BA Home with Large Fenced Yard – Near Downtown Thomasville
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, (23 reviews)
"Clean great location and very friendly thank you for the stay we will be back"
United States
ROBERT B.
Welcome to The Schoolhouse – A charming cottage in historic Monticello, Florida.
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, (3 reviews)
"Convenient location and has everything you need."
United States
Dee J.
The price is HK$1,173
HK$3,312 total
includes taxes & fees
8 Jun - 9 Jun
Southern Charm Home: Pool + Fireplace + Large Yard
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$748
HK$2,798 total
includes taxes & fees
6 Jul - 7 Jul
Tall Timbers Waterfront Oasis: 3BR / 2 BATH Retreat with Garage
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, (19 reviews)
"Charming house, nicely decorated and has everything one needs for staying. Great location to downtown Thomasville and other shopping. "
United States
Beth T.
The price is HK$1,520
HK$3,259 total
includes taxes & fees
8 Jun - 9 Jun
The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!
Interior

Dog friendly nature preserve Monticello, FL

Dog friendly nature preserve Monticello, FL
Monticello
10.0 out of 10, Exceptional, (2 reviews)
"Nice rustic environment and very pet friendly."
United States
Jeff B.
The price is HK$1,371
HK$1,673 total
includes taxes & fees
30 Jun - 1 Jul
Dog friendly nature preserve Monticello, FL
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

10/10 Excellent
"property was clean quiet and everything worked as it should. Continental breakfast better than average"
john 1-night trip
Posted 7 hours ago
Baymont by Wyndham Thomasville

Find out more about Boston

Search for holiday rentals in Boston on Expedia! You can easily find your home rentals, villas, holiday apartments in Boston using one of the methods below:

  • View our selection of featured holiday rentals in Boston
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  • Enter your travel dates to view the best deals on holiday rentals in Boston while they last

Look no further and take a look at our great range of rental properties in Boston!

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?

The Hansell House, your Downtown Thomasville Destination! Family + Pet Friendly!: This holiday home rental outside of Boston is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 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.