Boston Holiday Rentals

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Holiday Rentals in Boston

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (85)
"Lovely time at the house with 7 girls. Clean, perfect for a group this size. Beautiful property. Easy to check in and out."
The price is NZ$685
includes taxes & fees
29 June - 30 June
Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

Spacious room in ca. 1830 home

9.0 out of 10, Wonderful, (2)
"I have previously stayed at this location when it was operated as a bed and breakfast, this time it is only a lodging spot with complimentary drinks which was conveyed in the listing. The home is lovely and easily located in Orange, with quick access to many historical areas. While the Fenton is listed as having a bathroom, which it does, it is a tiny water closet at best. There is no standard size mirror or sink, the shower is also quite small. Overall, our stay was fine, but I did not like the...
The price is NZ$454
includes taxes & fees
30 June - 1 July
Spacious room in ca. 1830 home

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

10.0 out of 10, Exceptional, (6)
"Mint Cottage is a gem. Its spacious, beautifully furnished, and a great place to stay to explore Shenandoah National Park and its environs"
The price is NZ$731
includes taxes & fees
1 July - 2 July
Mint Cottage at Little Washington - a modern, spacious retreat with a view

Historic Madison Eagle Inn

10.0 out of 10, Exceptional, (7)
"Loved the location, we were in town for a Wedding at Reinback Barn. Very clean and loved the bed and linens!"
The price is NZ$477
includes taxes & fees
2 July - 3 July
Historic Madison Eagle Inn

Sojourners Rest: Old Rag Views, Hot Tub, Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (2)
"Had a great stay at Sojourner’s Rest! It’s a great location for exploring the NP and VA countryside. The house is clean and well equipped. The views of Old Rag are priceless. Be sure to walk down to the The Country Store in Etlan! "
The price is NZ$712
includes taxes & fees
1 July - 2 July
Sojourners Rest: Old Rag Views, Hot Tub, Fire Pit

Barn Apartment on Farm Near Old Rag and Shenandoah National Park

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay on the farm. Check in was easy, Jen was very accommodating and a wealth of information about the hikes and other things to do in the area."
Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

10.0 out of 10, Exceptional, (3)
"Loved it, clean and as described, great farm."
The price is NZ$184
includes taxes & fees
29 June - 30 June
Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

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

9.4 out of 10, Exceptional, (69)
"Nice place to stay for hiking."
The price is NZ$1,198
includes taxes & fees
29 June - 30 June
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Tranquil Hazel River Cabin – Perfect for Relaxation & Exploration. Pet Friendly

The price is NZ$726
includes taxes & fees
29 June - 30 June
Tranquil Hazel River Cabin – Perfect for Relaxation & Exploration. Pet Friendly

Spacious Retreat with Outdoor Firepit & Large Deck

9.6 out of 10, Exceptional, (26)
"This is a super nice place that is spacious, clean and comfortable.I would highly recommend!"
The price is NZ$463
includes taxes & fees
7 July - 8 July
Spacious Retreat with Outdoor Firepit & Large Deck

Walk to Old Rag* hot tub* 360 mountain views

10.0 out of 10, Exceptional, (20)
"Great house! Perfect for a hike at Old Ray. Nice owners too!"
The price is NZ$1,044
includes taxes & fees
7 July - 8 July
Walk to Old Rag* hot tub* 360 mountain views

Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub

2.0 star property
10.0 out of 10, Exceptional, (2)
"This was a great place to stay for a change of setting. So much more fun than a hotel room. The hot tub was a nice extra and bed was super comfortable. Nice to be able to have a cup of coffee and sit outside at picnic table. Great place!"
The price is NZ$563
includes taxes & fees
22 July - 23 July
Dream Dome - Romantic Retreat + Wifi A/C + Hot Tub

Zen Dome - Romantic Retreat + Wifi A/C + Hot Tub

2.0 star property
The price is NZ$819
includes taxes & fees
12 July - 13 July
Zen Dome - Romantic Retreat + Wifi A/C + Hot Tub

Ridgeview Mountain Cabin

9.4 out of 10, Exceptional, (41)
"Very well maintained, clean, gorgeous views. We'll be back next year."
The price is NZ$593
includes taxes & fees
29 June - 30 June
Ridgeview Mountain Cabin

Overlook Mountain Cabin

9.8 out of 10, Exceptional, (159)
"Beautiful mountain view! The trip was nice and beautiful! I love a good cozy vibe in the mountains! Communication with property manger was very excellent customer service! "
The price is NZ$615
includes taxes & fees
29 June - 30 June
Overlook Mountain Cabin

Shenandoah Mountain Cabin

10.0 out of 10, Exceptional, (14)
"This place is amazing! So clean and comfortable. Drive up to the cabin is very bumpy but so very worth it. "
The price is NZ$611
includes taxes & fees
30 June - 1 July
Shenandoah Mountain Cabin

Hideaway Mountain Cabin

10.0 out of 10, Exceptional, (11)
"Hideaway cabin was the perfect mountain getaway. My husband and I stayed here with our two dogs and it was so cozy and had everything we needed. The cabin was clean, and had all the essentials for cooking. The views are amazing and we loved using the wood fire stove. We took our dogs to the waterfall hike and they had a blast. Definitely recommend staying here! "
The price is NZ$615
includes taxes & fees
29 June - 30 June
Hideaway Mountain Cabin

Sunset Mountain Cabin

10.0 out of 10, Exceptional, (32)
"We loved this little getaway spot! The view was gorgeous and the cabin was so clean and cozy!"
The price is NZ$611
includes taxes & fees
30 June - 1 July
Sunset Mountain Cabin

Pet friendly home, pond, paddle boat, fishing gear, hiking, wineries, game room

10.0 out of 10, Exceptional, (2)
"We enjoyed our time at Lisa's place and walking around the property!"
The price is NZ$627
includes taxes & fees
29 June - 30 June
Pet friendly home, pond, paddle boat, fishing gear, hiking, wineries, game room

NEW! The Hilltop Station

6.0 out of 10, (1)
"A train came past the house at 7am in the morning. There is no mention of early morning train activity in the description. The mattresses were extremely soft and the blankets were very thin…so we were chilly. The house is beautiful…just these details are something to consider."
The price is NZ$663
includes taxes & fees
30 June - 1 July
NEW! The Hilltop Station
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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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?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Boston is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Boston?

Expedia has 4 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 Old Rag Mountain. In the wider area, you’ll find Little Washington Winery and Mary's Rock Summit Trailhead.

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.