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Boston Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Boston holiday rentals

A modern kitchen with a central island, bar stools, and pendant lighting.

1. Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Barn Apartment on Farm Near Old Rag and Shenandoah National Park
Etlan
10.0 out of 10, Exceptional, (31 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
The price is HK$941
HK$1,501 total
includes taxes & fees
20 Oct - 21 Oct
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A cabin with a wooden deck, two chairs, a red door, and a window.

2. Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.8 out of 10, Exceptional, (22 reviews)
"Hose was excellent, great communication, helpful, answered questions, even returned items inadvertently left behind. Location was great for activities around the national park and caverns."
United States
Tracy P.
The price is HK$636
HK$882 total
includes taxes & fees
26 Oct - 27 Oct
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A small, single-story wooden cabin with a white-framed door and a small porch.

3. Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.8 out of 10, Exceptional, (13 reviews)
"Perfect little house. Clean and very nice host."
United States
Debbie G.
The price is HK$699
HK$1,786 total
includes taxes & fees
18 Oct - 19 Oct
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A row of white-framed windows with a balcony, a bench, and a signboard.

4. Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
Amissville
9.8 out of 10, Exceptional, (90 reviews)
"The absolute nicest, cleanest Vrbo I have ever stayed at! Great communication from the host, the property did not disappoint. It was well stocked with everything needed. And very clear directions for using the property and a terrific folder with area information. Will return."
United States
Janet G.
The price is HK$1,860
HK$3,793 total
includes taxes & fees
15 Oct - 16 Oct
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

5. Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
Etlan
9.4 out of 10, Exceptional, (73 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is HK$3,496
HK$5,743 total
includes taxes & fees
26 Oct - 27 Oct
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
S'mores anyone?

6. Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Sperryville
10.0 out of 10, Exceptional, (31 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is HK$2,913
HK$6,139 total
includes taxes & fees
29 Oct - 30 Oct
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

7. Walk to Old Rag | Hot Tub | Mountain Farmhouse

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful house. Great location for hiking old rag."
United States
Jeffrey C.
The price is HK$2,249
HK$5,295 total
includes taxes & fees
3 Nov - 4 Nov
Walk to Old Rag | Hot Tub | Mountain Farmhouse
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

8. Charming 4-bedroom house in Madison centrally located!

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (3 reviews)
"Our stay was excellent. The host was responsive to every need. The house was beautiful. The view from the front window is beautiful!! The bathtub and shower in the main bathroom is luxurious!! We would be willing to stay there again."
United States
Lori K.
The price is HK$1,887
HK$3,655 total
includes taxes & fees
25 Oct - 26 Oct
Charming 4-bedroom house in Madison centrally located!
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

9. The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House

The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
Washington
10.0 out of 10, Exceptional, (22 reviews)
"Perfect location in town"
United States
Mona T.
The price is HK$1,020
HK$1,937 total
includes taxes & fees
27 Oct - 28 Oct
The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
A rustic outdoor seating area with a table and chairs surrounded by a forest.

10. Butterfly Camp near Old Rag Mountain and Shenandoah National Park

Butterfly Camp near Old Rag Mountain and Shenandoah National Park
Etlan
The price is HK$883
HK$1,376 total
includes taxes & fees
20 Oct - 21 Oct
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

11. Historic Madison Eagle Inn

Historic Madison Eagle Inn
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Great place - clean and very easy parking. The bed was comfortable too!"
United States
Tracy
The price is HK$1,091
HK$1,978 total
includes taxes & fees
3 Nov - 4 Nov
Historic Madison Eagle Inn
A living room with a grey sofa, a wooden staircase, a ceiling fan, and a 'Welcome' sign on the wall.

12. Cozy 1BR Apt Minutes From Skyline Drive!!

Cozy 1BR Apt Minutes From Skyline Drive!!
Amissville
9.6 out of 10, Exceptional, (48 reviews)
"Everything was clean, cute, and as advertised! The shower pressure"
United States
Kate O.
The price is HK$1,060
HK$1,975 total
includes taxes & fees
1 Nov - 2 Nov
Cozy 1BR Apt Minutes From Skyline Drive!!
A brick pathway leading to a fountain, surrounded by neatly trimmed hedges and a variety of plants.

13. The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi

The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
Washington
10.0 out of 10, Exceptional, (131 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is HK$1,256
HK$2,191 total
includes taxes & fees
2 Nov - 3 Nov
The Inn 1 min walk to Entire Colonial 3BR House Fast WiFi
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

14. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (66 reviews)
"Perfect little getaway."
United States
Vernon M.
The price is HK$1,373
HK$2,463 total
includes taxes & fees
25 Oct - 26 Oct
The Cabin at the Lake
A modern kitchen with a large island, pendant lighting, and a flat-screen TV.

15. Mint Cottage at Little Washington - a modern, spacious retreat with a view

Mint Cottage at Little Washington - a modern, spacious retreat with a view
Washington
10.0 out of 10, Exceptional, (15 reviews)
"Perfect spot for a couple visiting the area or dining at the Inn. "
United States
Greg S.
The price is HK$3,735
HK$4,859 total
includes taxes & fees
9 Nov - 10 Nov
Mint Cottage at Little Washington - a modern, spacious retreat with a view
A modern living room with a grey sofa, striped ottoman, and a view of a green landscape through large windows.

16. Creekside Cabin: Hot Tub, Cinema, EV Charger, Dogs

Creekside Cabin: Hot Tub, Cinema, EV Charger, Dogs
Luray
10.0 out of 10, Exceptional, (4 reviews)
"Solid location to park "
United States
Lauren E.
The price is HK$1,657
HK$3,684 total
includes taxes & fees
3 Nov - 4 Nov
Creekside Cabin: Hot Tub, Cinema, EV Charger, Dogs
A hotel room with two beds, a nightstand with a globe and a plant, and a framed picture on the wall.

17. Charming Cottage w/ Incredible Views & Firepit

Charming Cottage w/ Incredible Views & Firepit
Stanley
10.0 out of 10, Exceptional, (25 reviews)
"Pet friendly. Great scenery. Hot tub. Fire pit. Very relaxing and comfortable."
United States
Laura M.
The price is HK$1,286
HK$3,103 total
includes taxes & fees
4 Nov - 5 Nov
Charming Cottage w/ Incredible Views & Firepit
A garden pathway with various plants and a statue.

18. The Blenheim Suite in historic Holladay House

The Blenheim Suite in historic Holladay House
Orange
10.0 out of 10, Exceptional, (5 reviews)
"Had a weekend visit and location worked very well. Enjoyed my visit."
United States
Merrie Mac S.
The price is HK$1,844
HK$2,744 total
includes taxes & fees
19 Oct - 20 Oct
The Blenheim Suite in historic Holladay House
A living room with a large window, a television, a fireplace, and a table with candles.

19. Deck & Pasture Views! Bealeton Farmhouse Escape

Deck & Pasture Views! Bealeton Farmhouse Escape
3.0 star property
Bealeton
The price is HK$1,067
HK$3,721 total
includes taxes & fees
15 Oct - 16 Oct
Deck & Pasture Views! Bealeton Farmhouse Escape
A wooden cabin with a deck, outdoor seating, and a fire pit.

20. Balk Retreat/MountainViews/HotTub/Firepit

Balk Retreat/MountainViews/HotTub/Firepit
Stanley
10.0 out of 10, Exceptional, (5 reviews)
"We had a great time here. Well appointed and loved the extra touches they had for the dog and families with small kids. "
United States
Spencer P.
The price is HK$690
HK$2,724 total
includes taxes & fees
21 Oct - 22 Oct
Balk Retreat/MountainViews/HotTub/Firepit
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

Comfort Inn & Suites Orange - Montpelier

Comfort Inn & Suites Orange - Montpelier

8/10 Good
"Pretty good"
Amanda 1-night trip
Posted 13 hours ago
Comfort Inn & Suites Orange - Montpelier

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
  • Use the map to find apartments and other holiday homes in the Boston neighbourhood you prefer
  • 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

Can I find a holiday rental 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. Boston is known for its restaurants and parks.

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

Shenandoah Valley Yurt: This holiday home rental outside of Boston comes with air conditioning so that you can feel at home during your trip.

How many holiday rentals are there in Boston?

Expedia has 3 holiday rentals for your stay in Boston.

What can I see and do in Boston?

While exploring the area, visit family-friendly sights like Yogi Bear's Jellystone Park, or get outside and enjoy nature at Shenandoah National Park. In the wider area, you’ll find Culpeper National Cemetery and Old Rag Mountain.

What are holiday rentals like in Boston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Boston. Holiday rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.