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Boston Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Boston holiday rentals

A small, single-story wooden cabin with a white-framed door and a small porch.

1. 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, (11 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
The price is HK$698
HK$1,784 total
includes taxes & fees
27 Aug - 28 Aug
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
A modern kitchen with a central island, bar stools, and pendant lighting.

2. 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, (23 reviews)
"Fantastic place, so relaxing and beautiful. Host was responsive and extremely helpful. "
United States
Mack
The price is HK$833
HK$1,363 total
includes taxes & fees
31 Aug - 1 Sept
Barn Apartment on Farm Near Old Rag and Shenandoah National Park
A log cabin interior with a wooden ceiling, a black leather sofa, white armchairs, and a rustic dining area.

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

Walk to Old Rag | Hot Tub | Mountain Farmhouse
Sperryville
10.0 out of 10, Exceptional, (24 reviews)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
United States
Mary Margaret R.
The price is HK$2,013
HK$4,501 total
includes taxes & fees
31 Aug - 1 Sept
Walk to Old Rag | Hot Tub | Mountain Farmhouse
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$1,858
HK$3,838 total
includes taxes & fees
27 Aug - 28 Aug
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, (72 reviews)
"Wonderful house and great setting; will go back!"
United States
Jay R.
The price is HK$3,492
HK$5,692 total
includes taxes & fees
27 Aug - 28 Aug
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

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, (27 reviews)
"The property was great -- would definitely book again!"
United States
Everett R.
The price is HK$1,793
HK$4,407 total
includes taxes & fees
31 Aug - 1 Sept
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
A cabin with a wooden deck, two chairs, a red door, and a window.

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

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
Etlan
9.6 out of 10, Exceptional, (18 reviews)
"Great host. Super clean. Excellent driving directions and walking info to get to the cabin. Awesome solution for people who love camping"
United States
Patrick
The price is HK$635
HK$881 total
includes taxes & fees
31 Aug - 1 Sept
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park
A woman standing in a well-manicured garden with hedges and flower beds.

8. 1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.

1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
Washington
10.0 out of 10, Exceptional, (20 reviews)
"Perfect location in town"
United States
Mona T.
The price is HK$953
HK$1,805 total
includes taxes & fees
31 Aug - 1 Sept
1-Min Walk to The Inn • Private Suite, Tub & Full Kitchen.
A covered deck with blue and turquoise Adirondack chairs, a white chair, and a green doormat.

9. The Cabin at the Lake

The Cabin at the Lake
Madison
9.6 out of 10, Exceptional, (62 reviews)
"Great view and access to the lake!"
United States
Leti H.
The price is HK$1,234
HK$2,324 total
includes taxes & fees
1 Sept - 2 Sept
The Cabin at the Lake
A spacious dining area with a central table surrounded by chairs, a chandelier, and wine bottles on the table.

10. 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$1,097
HK$2,010 total
includes taxes & fees
24 Sept - 25 Sept
Historic Madison Eagle Inn
A conservatory with a glass ceiling, wicker furniture, and potted plants.

11. 1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .

1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
Washington
10.0 out of 10, Exceptional, (128 reviews)
"Really enjoyed the stay—great house, clean, and perfect for a relaxing weekend."
United States
Daniel R.
The price is HK$1,214
HK$2,162 total
includes taxes & fees
2 Sept - 3 Sept
1min walk to The Inn • Entire Colonial 3BR House Fast WiFi, tub & full kitchen .
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, (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$1,607
HK$3,341 total
includes taxes & fees
13 Sept - 14 Sept
Charming 4-bedroom house in Madison centrally located!
A wooden deck with a table and chairs, overlooking a scenic landscape with trees and hills.

13. "The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Rileyville
9.8 out of 10, Exceptional, (333 reviews)
"A few spiders but the cabin was amazing, great views!"
United States
Jackson C.
The price is HK$1,223
HK$2,178 total
includes taxes & fees
28 Aug - 29 Aug
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
A spacious wooden cabin with a high ceiling, a fireplace, a television, and a cozy seating area.

14. Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
Luray
10.0 out of 10, Exceptional, (76 reviews)
"Everything about this property was great. I would stay again."
United States
Sonya H.
The price is HK$2,293
HK$4,315 total
includes taxes & fees
30 Aug - 31 Aug
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

15. 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$882
HK$1,374 total
includes taxes & fees
30 Aug - 31 Aug
Butterfly Camp near Old Rag Mountain and Shenandoah National Park
A modern kitchen with a large island, bar stools, and a built-in oven.

16. Luxe Tiny NEW Hot Tub, Pool & Cold Plunge, Near SNP

Luxe Tiny NEW Hot Tub, Pool & Cold Plunge, Near SNP
Luray
9.8 out of 10, Exceptional, (6 reviews)
"This home was amazing! My daughters especially loved the cozy loft area. We hiked all day in Shenandoah and enjoyed cooking dinners at home - the kitchen had everything we needed. Bear Mt Ziplining is close by and it was a blast. We also enjoyed the Luray Caverns. We did a lot of hikes in Shenandoah, but the closest one was Mary's Rock and it was a hit! Would def recommend this mt retreat. Check-in & out was a breeze. The home was super clean and the vibe was so calming. "
United States
Catherine B.
The price is HK$1,662
HK$2,964 total
includes taxes & fees
27 Aug - 28 Aug
Luxe Tiny NEW Hot Tub, Pool & Cold Plunge, Near SNP
A modern kitchen with a large island, pendant lighting, and a flat-screen TV.

17. 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, (13 reviews)
"Perfect spot for a couple visiting the area or dining at the Inn. "
United States
Greg S.
The price is HK$2,817
HK$3,717 total
includes taxes & fees
1 Sept - 2 Sept
Mint Cottage at Little Washington - a modern, spacious retreat with a view
A yellow door with a 'Welcome' sign, a kitchen area with a wooden countertop and stools, and a clock on the wall.

18. Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (102 reviews)
"Great location close to Main Street. Rooms were clean and kitchen was pretty well stocked. Lovely home!"
United States
Lia C.
The price is HK$917
HK$2,033 total
includes taxes & fees
27 Aug - 28 Aug
Historical home, walkable to many restaurants and shops.
A single-story house with a gabled roof, a front porch with a bench, and a front door.

19. Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Luray
9.8 out of 10, Exceptional, (104 reviews)
"Place was very clean and well equipped."
United States
Suze F.
The price is HK$1,191
HK$2,503 total
includes taxes & fees
27 Aug - 28 Aug
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
A hot tub with a view of a forest.

20. Mountains & Privacy: Perfect for Couples/Sm Groups

Mountains & Privacy: Perfect for Couples/Sm Groups
Stanley
10.0 out of 10, Exceptional, (72 reviews)
"Perfect cabin for our fall getaway for 2! Hot tub was the perfect place to relax after exploring the beautiful scenery near by! "
United States
Crystal S.
The price is HK$1,852
HK$2,426 total
includes taxes & fees
27 Aug - 28 Aug
Mountains & Privacy: Perfect for Couples/Sm Groups
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

10/10 Excellent
"For the money you can't beat this place. Its old but you can tell they absolutely keep everything clean. Even the yard was landscaped way nicer than most motel 6. Very friendly people"
Teddy 1-night trip
Posted less than an hour ago
Motel 6 Culpeper, VA

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 Copper Fox Distillery 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.