Holiday Rentals in Boston

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Boston

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

The price is €194
includes taxes & fees
31 Jul - 1 Aug
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

4BR Retreat Near Wineries, Weddings & Hiking

10.0 out of 10, Exceptional, (32)
"Stephen makes everyone feel welcome and comfortable in his beautiful house. Great comfy beds, amazing back yard and great breakfasts. I have already booked for next year!"
The price is €766
includes taxes & fees
21 Jul - 22 Jul
4BR Retreat Near Wineries, Weddings & Hiking

Nestled Among Majestic Trees, Hilltop Hideaway is a Woodland Sanctuary

9.8 out of 10, Exceptional, (86)
"Great place that works well for Rixey Manor weddings "
The price is €372
includes taxes & fees
18 Jul - 19 Jul
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 €237
includes taxes & fees
31 Jul - 1 Aug
Spacious room in ca. 1830 home

Charming Private Suite in Historic Colonial House – right beside from The Inn!

10.0 out of 10, Exceptional, (14)
"an excellent option if dining at the INN"
The price is €206
includes taxes & fees
4 Aug - 5 Aug
Charming Private Suite in Historic Colonial House – right beside from The Inn!

Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

10.0 out of 10, Exceptional, (119)
"The house was comfy and well appointed. The owners have made every effort to cover whatever you might need while staying in the home. "
Colonial 3BR Home • Walk to The Inn • Great Location • Fast Wi-Fi

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 €422
includes taxes & fees
30 Jul - 31 Jul
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 €253
includes taxes & fees
31 Jul - 1 Aug
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 €368
includes taxes & fees
21 Jul - 22 Jul
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."
The price is €183
includes taxes & fees
31 Jul - 1 Aug
Barn Apartment on Farm Near Old Rag and Shenandoah National Park

Moonshine Glamping Cabin near Old Rag Mountain in Shenandoah National Park

9.6 out of 10, Exceptional, (4)
"Loved it, clean and as described, great farm."
The price is €100
includes taxes & fees
30 Jul - 31 Jul
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 €639
includes taxes & fees
30 Jul - 31 Jul
Spectacular Spirit Dancer 4 bedrooms, 1 den w/bed, Luxurious on 60 private acres

Spacious Retreat with Outdoor Firepit & Large Deck

9.6 out of 10, Exceptional, (28)
"This is a super nice place that is spacious, clean and comfortable.I would highly recommend!"
The price is €248
includes taxes & fees
22 Jul - 23 Jul
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 €558
includes taxes & fees
29 Jul - 30 Jul
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!"
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 €378
includes taxes & fees
31 Jul - 1 Aug
Zen Dome - Romantic Retreat + Wifi A/C + Hot Tub

Ridgeview Mountain Cabin

9.4 out of 10, Exceptional, (41)
"This was the perfect little cabin for me and my husband. The location was perfect for us. We went to the Laray Caverns and hiked Old Rag. The owner was very helpful and has great communication! Planning another trip soon! "
The price is €307
includes taxes & fees
27 Jul - 28 Jul
Ridgeview Mountain Cabin

Overlook Mountain Cabin

9.8 out of 10, Exceptional, (160)
"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 €317
includes taxes & fees
30 Jul - 31 Jul
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 €327
includes taxes & fees
21 Jul - 22 Jul
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 €336
includes taxes & fees
27 Jul - 28 Jul
Hideaway Mountain Cabin
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.
Save an average of 15% on thousands of hotels when you're signed in

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.