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Boston Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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, (36 reviews)
"Kids absolutely loved the property with many kinds of animals!"
United States
Ikuo
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, (25 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 AU$149
includes taxes & fees
15 Nov - 16 Nov
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, (17 reviews)
"Very comfortable and clean space. Plenty of room for 1 or 2 people. Check in and out instructions were very detailed. Price was very affordable compared to the nicer hotels in town who were charging $200 to $300 a night. Kind of out in the country but its easy to get to and from town, pretty straight stretch. I was only there in the evenings and everything was very quiet and peaceful."
United States
emily
The price is AU$324
includes taxes & fees
18 Nov - 19 Nov
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

4. 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 AU$333
includes taxes & fees
2 Nov - 3 Nov
The Inn 1-Min Walk to Private Suite with Full Kitchen in 3BR Colonial House
A two-story house with a front porch, a covered entryway, and a visible front yard.

5. 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, (92 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 AU$634
includes taxes & fees
2 Nov - 3 Nov
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary
A hallway with a wooden bench, a red door, and a framed picture on the wall.

6. 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 AU$338
includes taxes & fees
2 Nov - 3 Nov
Historic Madison Eagle Inn
A white house with a green roof, a porch with chairs, and a fire pit with chairs around it.

7. Quiet suite w/ outdoor furniture

Quiet suite w/ outdoor furniture
Luray
9.0 out of 10, Wonderful, (10 reviews)
"The Legacy Inn in Luray was great! Easy to find, easy entry (with a code), within walking distance of dining and outdoor music, and an easy drive to Luray Caverns and Shenandoah National Park. Highly recommend."
United States
Robert
The price is AU$231
includes taxes & fees
8 Nov - 9 Nov
Quiet suite w/ outdoor furniture
S'mores anyone?

8. 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, (32 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is AU$852
includes taxes & fees
17 Nov - 18 Nov
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.

9. 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 AU$872
includes taxes & fees
9 Nov - 10 Nov
Walk to Old Rag | Hot Tub | Mountain Farmhouse
A living room with a grey sofa, a wooden staircase, a ceiling fan, and a 'Welcome' sign on the wall.

10. 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 AU$313
includes taxes & fees
2 Nov - 3 Nov
Cozy 1BR Apt Minutes From Skyline Drive!!
A spacious living room with a high wooden ceiling, large windows, a sofa, armchairs, a coffee table, and a dining area.

11. 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, (74 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is AU$1,051
includes taxes & fees
3 Nov - 4 Nov
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

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

Charming 4-bedroom house in Madison centrally located!
Madison
10.0 out of 10, Exceptional, (4 reviews)
"The home met all our family’s needs during a weekend stay for a party at nearby farm. The layout and outdoor spaces were a bonus. In fact, the view of Hawksbill Mountain from the porch while enjoying our morning coffee: priceless. And importantly easy access to Rt 29 and the town but yet secluded and bucolic."
United States
B D.
The price is AU$670
includes taxes & fees
2 Nov - 3 Nov
Charming 4-bedroom house in Madison centrally located!
Interior

13. 37-Acre Private Cabin Retreat near Shenandoah

37-Acre Private Cabin Retreat near Shenandoah
Stanley
The price is AU$546
includes taxes & fees
3 Nov - 4 Nov
37-Acre Private Cabin Retreat near Shenandoah
A garden with a central fountain, surrounded by neatly trimmed hedges and a brick pathway.

14. 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, (132 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is AU$390
includes taxes & fees
9 Nov - 10 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.

15. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (67 reviews)
"Perfect little getaway."
United States
Vernon M.
The price is AU$394
includes taxes & fees
3 Nov - 4 Nov
The Cabin at the Lake
Living area

16. Dog-Friendly Downtown Studio — Walk to Park, Shops

Dog-Friendly Downtown Studio — Walk to Park, Shops
Luray
10.0 out of 10, Exceptional, (14 reviews)
"Excellent communication throughout the entire stay and booking. Clean property and close to main strip. Would recommend to others looking to stay in Luray."
United States
Sebastiano
The price is AU$304
includes taxes & fees
9 Nov - 10 Nov
Dog-Friendly Downtown Studio — Walk to Park, Shops
A white house with blue shutters and a porch.

17. Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park
Luray
9.8 out of 10, Exceptional, (17 reviews)
"The cottage is a great place to stay. Everything was very ckean. The cottage was well supplied. It was just right for our tours of the wineries in the area, Ruth the owner was very friendly."
United States
Kathleen M.
Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park
A living room with a large window, a television, a fireplace, and a table with candles.

18. Deck & Pasture Views! Bealeton Farmhouse Escape

Deck & Pasture Views! Bealeton Farmhouse Escape
Bealeton
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful home situated in a rural area. Bedding was very cozy! "
United States
Gerrie S.
The price is AU$610
includes taxes & fees
15 Nov - 16 Nov
Deck & Pasture Views! Bealeton Farmhouse Escape
A row of townhouses with a central entrance, each with a garage and a small front yard.

19. Modern 3BR Townhome, 3 Min to Luray Caverns & Near Shenandoah, Pets Welcome

Modern 3BR Townhome, 3 Min to Luray Caverns & Near Shenandoah, Pets Welcome
Luray
10.0 out of 10, Exceptional, (62 reviews)
"We really enjoyed our stay. The townhome was very clean, comfortable, and well prepared for guests. We especially appreciated all the thoughtful essentials and little touches provided for travelers — they made us feel very welcome from the moment we arrived. The location is excellent, especially for anyone visiting Luray Caverns and exploring the Shenandoah area. It was very convenient and worked perfectly for our visit. Aline and Bart were wonderful hosts and communicated clearly and promptly...
United States
Delianne
The price is AU$390
includes taxes & fees
13 Nov - 14 Nov
Modern 3BR Townhome, 3 Min to Luray Caverns & Near Shenandoah, Pets Welcome
A spacious living room with a grey sofa, a coffee table, and a large window.

20. 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 AU$494
includes taxes & fees
4 Nov - 5 Nov
Charming Cottage w/ Incredible Views & 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

Round Hill Inn

Round Hill Inn

10/10 Excellent
"This hotel is in an unbeatable location at the top of a hill where it looks down over everything around it. Super cool to walk around and see the sites. The room was clean, both front desk and housekeeping staff were really helpful, and had a great stay."
Daniel 2-night trip
Posted 3 hours ago
Round Hill Inn

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 favourite 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 depend 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 AU$149 per night. Entering your travel dates in the search wizard might find you 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.