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Boston Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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 NZ$335
includes taxes & fees
13 Oct - 14 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, (21 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 NZ$200
includes taxes & fees
12 Oct - 13 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 NZ$396
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 NZ$857
includes taxes & fees
12 Oct - 13 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 NZ$1,270
includes taxes & fees
12 Oct - 13 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, (29 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is NZ$1,366
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 NZ$1,168
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 NZ$814
includes taxes & fees
12 Oct - 13 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 NZ$430
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 NZ$312
includes taxes & fees
12 Oct - 13 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 NZ$435
includes taxes & fees
2 Nov - 3 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, (47 reviews)
"Everything was clean, cute, and as advertised! The shower pressure"
United States
Kate O.
The price is NZ$415
includes taxes & fees
12 Oct - 13 Oct
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 NZ$482
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, (64 reviews)
"Great view and access to the lake!"
United States
Leti H.
The price is NZ$522
includes taxes & fees
12 Oct - 13 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 NZ$944
includes taxes & fees
2 Nov - 3 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.
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 NZ$710
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 NZ$621
includes taxes & fees
12 Oct - 13 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 NZ$844
includes taxes & fees
14 Oct - 15 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 NZ$621
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

Motel 6 Culpeper, VA

Motel 6 Culpeper, VA

8/10 Good
"The welcome and staff we encountered at the reception were friendly & efficient. The room (18) had been updated and was very clean. As it had been recently cleaned there was a smell of detergent but better that than the opposite! There was only soap provided but as it was a one night stay that was okay asI do not like the single use plastic shampoos etc. The room was way too light during the night - this could be improved. There was no coffee making appliance in the room but there was good coffee at reception in the morning. Overall it was a no frills but clean stay. Easy parking and close to the town & dining. Would stay here again."
Joanna 1-night trip
Posted 5 hours ago
Motel 6 Culpeper, VA

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$200 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

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.