Chilmark Vacation Rentals from $62: Search Short-Term Rentals

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Our top choices for Chilmark vacation rentals

A tent with a bed inside, a colorful rug, and a sign on the ground.

1. Stone Circle Glamping

Durrington

Darnell

$52 nightly

Aug 31 - Sep 1

Total with taxes and fees

A two-story building with a blue storefront labeled "The Dorsel Store."

2. A spacious, well equipped private annexe with garden and parking in Shaftesbury.

Shaftesbury Dorset

Martin K.

$160 nightly

Aug 31 - Sep 1

Total with taxes and fees

A traditional brick house with a gabled roof, surrounded by lush greenery and flowering plants.

3. Beautiful, traditional rural cottage

Shrewton

Michael

$224 nightly

Sep 10 - Sep 11

Total with taxes and fees

A white house with a tiled roof, surrounded by a well-maintained lawn and garden, with a clear view of the surrounding countryside.

4. Church View

Salisbury

$810 nightly

Sep 23 - Sep 24

Total with taxes and fees

A compact living space with a kitchenette, a dining area, and a sofa.

5. The Orchid

Gillingham

$121 nightly

Sep 3 - Sep 4

Total with taxes and fees

A sign for Hotel Peartree, a serviced apartment, with contact information and website.

6. Peartree Serviced Apartments

Salisbury

Jayne

$172 nightly

Sep 27 - Sep 28

Total with taxes and fees

A wooden arbor with pink blossoms, a brick pathway, and a house with a blue roof in the background.

7. Cozy & Self Contained The Garden Annex 306

Salisbury

Dala B.

$158 nightly

Sep 15 - Sep 16

Total with taxes and fees

A stone house with a gravel pathway leading to a wooden fence.

8. The Dog House, Mere - Dog Friendly with EV Charger

Mere

$136 nightly

Sep 3 - Sep 4

Total with taxes and fees

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Top Chilmark Hotel Reviews

Homewood Hotel & Spa

10/10 Excellent

"We loved our stay at Homewood, it was the perfect place for a totally relaxing, luxury mini-break. The location is stunning, the hotel was full of charm and every detail had been thought about. Super-friendly, helpful staff and the spa facilities were great. The dinner was delicious with fresh flavours, generous portions and the breakfast was at the same standard. Highly recommended"

The George Hotel, Amesbury, Wiltshire

8/10 Good

"The hotel has a pleasant atmosphere. The beer garden is nice with beautiful hanging baskets. The rooms are adequate if a little compact. Toiletries are provided and are lovely. Toilets in the bar area are clean and contain the same toiletries. The lunch and dinner menu includes gluten free options which was required by my husband. Would return"

Best Western Red Lion Hotel

8/10 Good

"Atmospheric inn located near the marketplace and high street shopping. Very helpful staff. The historic inn is very well maintained but halls are narrow and floors uneven reflecting its age. The bed was comfortable. The bathroom is fine but basic and unfortunately the fixed showerhead is poorly situated unless you are very tall. An added handheld option for flexibility would be much better. There is a nice bar but no dinner service, although solid options are close by. All in all I enjoyed my overnight stay."

Old Mill Salisbury

10/10 Excellent

"Enjoyable stay at this venue.the Room was delightfully decorated spacious and well equipped,there was a Tassimo Coffee machine, better than the usual instant sashes that you normally get. The Breakfast was a bit disappointing average and pricy but ok. Outside the River Avons Mill race ememinates out from underneath the building the town walk way leads a comfortable route to the Rail Station or Town centre,with views toward the Cathedral."

The Chapter House

10/10 Excellent

"Unique historic property. A restaurant with rooms … definitely not your usual chain hotel room. In a building hundreds of years old the floors and stairs are very wonky … so mind your step! We loved the character of the buildings and our room (no. 6 … not all rooms have wood panelling this dark!) … it was spacious and had everything we needed. And the food in the restaurant was great … both for evening meal and breakfast."

The Merchant's House, BW Signature Collection

10/10 Excellent

"My third time staying at this hotel and I can’t fault it again. The room was lovely and the perfect size just for me. If I was taller I would have said the shower was a bit in the short side but at 5’7 it was perfect. The air con was also a god send in the heatwave"

Sandy Balls Holiday Village

8/10 Good

"Cabin wasn’t clean, we have a 13 month old baby, so as soon as we moved the sofa towards the wall and pulled back the curtain, dead flies and food and could tell hoovering had just been swished around the floor and no furniture had been moved for many cleans. Amenities great for age 3 plus but lacking in things for 1 year olds. No area or pen or soft play or outdoor play that you can pop a 13 month old down in, so fighting for our lives a little. He loves a swim and we hired bikes and he loves a bike ride and hike but hard to not put him down to play anywhere easily. Liked the baby disco and meeting the big bear on an evening but again will be best when age 3+. Would come again but not with a baby - cots cost extra in our accommodation and should offer a high chair in the cabins too. Oh and I had no signal or WiFi hardly anywhere - I’m on o2!"

Find out more about Chilmark

Everything you need to know about Chilmark vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Chilmark vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chilmark vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chilmark in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark vacation 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 Chilmark 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 Chilmark vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. 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 vacation rental in Chilmark?

Yes, there are vacation rentals close to the most popular sights in Chilmark, or you can choose a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Chilmark?

STUNNING LARGE COUNTRY FAMILY HOME, INDOOR POOL, SLEEPS 12, SECLUDED GARDEN: Visitors like this Chilmark vacation home rental. It is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Chilmark?

While exploring the area, visit family-friendly sights like Larmer Tree Gardens, or get outside and enjoy nature at Cranborne Chase and the West Wiltshire Downs. In the larger area, you’ll find Stonehenge and Wilton House.

What’s a vacation rental in Chilmark like?

Vacation rentals are private properties you can book for short or long periods in Chilmark. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family getaway.

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Our top choices for Chilmark vacation rentals

1. Stone Circle Glamping

2. A spacious, well equipped private annexe with garden and parking in Shaftesbury.

3. Beautiful, traditional rural cottage

4. Church View

5. The Orchid

6. Peartree Serviced Apartments

7. Cozy & Self Contained The Garden Annex 306

8. The Dog House, Mere - Dog Friendly with EV Charger

9. Rook Lane House

10. Tranquil Retreat in Pewsey Countryside

11. Newly Renovated 2-Bed House w/ Parking – Sleeps 5 Near Shaftesbury Town

12. Rose Barn - Recently converted self-contained flat

13. Charming single-storey hideaway with garden access, perfect for couples

14. The Mews Cottage

15. Charles Hope Salisbury Centre

16. The Retreat ~ Charming & Cozy Gem ~ Sauna ~ HotTub

17. 1 bedroom accommodation in Burgate, near Fordingbridge

18. Farm Cottage on a Secluded 9-acre Equestrian Small Holding

19. Modern 2-bedroom house with spacious large garden in beautiful Westbury

20. Pewsey Countryside Dome - Dog Friendly - Fire pit

Find vacation rentals that suit your style

Top Chilmark Hotel Reviews

Homewood Hotel & Spa

Crown Hotel

The George Hotel, Amesbury, Wiltshire

The Riverside, WorldHotels Distinctive

Best Western Red Lion Hotel

Old Mill Salisbury

The Chapter House

The Merchant's House, BW Signature Collection

Sandy Balls Holiday Village

Find out more about Chilmark

Frequently asked questions

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