Wiltshire Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Wiltshire vacation rentals

Bev Rosevilla

Bev Rosevilla
2.5 star property
Rhyne Park Village
The price is CA $117
CA $177 total
includes taxes & fees
Mar 25 - Mar 26
Bev Rosevilla

Serenitys Hideaway Montego Bay

Serenitys Hideaway Montego Bay
3.5 star property
Montego Bay
The price is CA $103
CA $258 total
includes taxes & fees
Apr 1 - Apr 2
Serenitys Hideaway Montego Bay

Short and longTerm ,Vacational rental home.

Short and longTerm ,Vacational rental home.
Rhyne Park Village
8.8 out of 10, Excellent, (3 reviews)
"Kadean is the best!.. very helpful everyday of my stay.."
United States
Julia M.
The price is CA $124
CA $151 total
includes taxes & fees
Mar 25 - Mar 26
Short and longTerm ,Vacational rental home.

Sunshine Lodge- Your Home Away From Home

Sunshine Lodge- Your Home Away From Home
4.0 star property
Montego Bay
7.4 out of 10, Good, (3 reviews)
"It was beautiful on the inside and had an amazing view of Montego Bay."
United States
AGNES
The price is CA $105
CA $130 total
includes taxes & fees
Apr 1 - Apr 2
Sunshine Lodge- Your Home Away From Home

Half Hill 3BR

Half Hill 3BR
3.5 star property
Montego Bay
The price is CA $472
CA $681 total
includes taxes & fees
Mar 25 - Mar 26
Half Hill 3BR

Eden Luxe 1

Eden Luxe 1
2.5 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful. Staff was friendly and helpful with the check in process. Will be planning another visit in the near future."
United States
Kelleia
The price is CA $630
CA $829 total
includes taxes & fees
Apr 1 - Apr 2
Eden Luxe 1

Serenity Suite; The Jamaican Retreat

Serenity Suite; The Jamaican Retreat
Montego Bay
The price is CA $96
CA $137 total
includes taxes & fees
Mar 26 - Mar 27
Serenity Suite; The Jamaican Retreat

Oceanview Studio Apt w/ Pool, Bar & Beach Access

Oceanview Studio Apt w/ Pool, Bar & Beach Access
3.0 star property
Montego Bay
6.0 out of 10, (2 reviews)
"The Oceanview was prefect. Allowed me to stay for an additional tonight with discount. Neighbors very friendly and helpful. The pool stays open 24 hours. Need a pass to get on the beach which locks at 6 pm. The Restaurant was great not over priced menu. There's a bar/gift shop on the premise. "
United States
Kinshasha
Oceanview Studio Apt w/ Pool, Bar & Beach Access

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts
Mount Salem
10.0 out of 10, Exceptional, (1 review)
"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...
United States
English C.
The price is CA $69
CA $110 total
includes taxes & fees
Mar 31 - Apr 1
Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Impeccable Spacious 3 Bedroom Home Near Beach!

Impeccable Spacious 3 Bedroom Home Near Beach!
Montego Bay
9.0 out of 10, Wonderful, (7 reviews)
"Our stay at this property was pleasant, relaxing and quiet. Host was very responsive and checked in during our stay to make sure all was well. There is a local grocery store and restaurant within walking distance which was a plus. Will definitely stay again!"
United States
Bridgette E.
The price is CA $124
CA $220 total
includes taxes & fees
Apr 4 - Apr 5
Impeccable Spacious 3 Bedroom Home Near Beach!

Hideaway by the Sea

Hideaway by the Sea
Montego Bay
9.8 out of 10, Exceptional, (37 reviews)
"Very clean space and Sherri thought of every convenience you could need that made my stay very comfortable "
United States
Renardo
The price is CA $86
CA $173 total
includes taxes & fees
Mar 29 - Mar 30
Hideaway by the Sea

Dragon fly Cottage

Dragon fly Cottage
Cave
10.0 out of 10, Exceptional, (7 reviews)
"We had a lot of fun relaxing here. Geneva made excellent breakfast and suppers and we spent the majority of our time relaxing on the deck/hammock reading and hiking around the property and the town of Kentucky. If you want an escape from the tourism scene, this is a nice place to go! "
Canada
Kaili
The price is CA $87
CA $114 total
includes taxes & fees
Mar 26 - Mar 27
Dragon fly Cottage

Firefly cottage with Ocean view

Firefly cottage with Ocean view
Cave District
10.0 out of 10, Exceptional, (27 reviews)
"I would recommend this cabin resort to anyone. Geneva was wonderful host, along with her beautiful family"
United States
Rick B.
The price is CA $80
CA $108 total
includes taxes & fees
Mar 25 - Mar 26
Firefly cottage with Ocean view

Unity Villa

Unity Villa
3.0 star property
Montego Bay
8.0 out of 10, Very good, (1 review)
"I LIKE HOW THEY COMMUNICATED AND ADDRESSED THE PROBLEMS ! Only thing I didn’t like was the no working ac and there wasn’t stuff close to go shop "
United States
Susan
Unity Villa

Montego Bay Ironshore Luxury Studios

Montego Bay Ironshore Luxury Studios
3.0 star property
Ironshore
9.4 out of 10, Exceptional, (25 reviews)
"Comfortable, clean and quiet. I would stay here again "
United States
Shane
The price is CA $130
CA $151 total
includes taxes & fees
Apr 8 - Apr 9
Montego Bay Ironshore Luxury Studios

Hospitality Expert CB1: Pool, Beach & Chef

Hospitality Expert CB1: Pool, Beach & Chef
Montego Bay
9.2 out of 10, Wonderful, (9 reviews)
"Had a good experience shower pressure, and bathroom flushing was a lil problem otherwise all was well for me"
United States
Kevin D.
The price is CA $215
CA $367 total
includes taxes & fees
Apr 1 - Apr 2
Hospitality Expert CB1: Pool, Beach & Chef

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning
3.0 star property
Montego Bay
10.0 out of 10, Exceptional, (1 review)
The price is CA $120
CA $366 total
includes taxes & fees
Apr 22 - Apr 23
YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Kimoya's cottage is a mountain cottage overlooking the sea and coastline
Cave
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely gorgeous property and views, bird sounds, fantastic food prepared by the friendly hosts. Simple living with wi-fi if needed."
United States
David G.
The price is CA $82
CA $110 total
includes taxes & fees
Mar 25 - Mar 26
Kimoya's cottage is a mountain cottage overlooking the sea and coastline

Quiet relaxing mountainous get away!

Quiet relaxing mountainous get away!
Montego Bay
9.2 out of 10, Wonderful, (5 reviews)
"The location was gorgeous, not far from the city. Easy/beautiful walk to cabs. Host was great and the bed/sheets felt great!!"
United States
Kintoria W.
The price is CA $96
CA $137 total
includes taxes & fees
Mar 25 - Mar 26
Quiet relaxing mountainous get away!

Newly Furnished 1 Bedroom Apartment - Montego Bay

Newly Furnished 1 Bedroom Apartment - Montego Bay
Ironshore
8.0 out of 10, Very good, (5 reviews)
"Our stay was upgraded to a townhouse due to over booking. Really beautiful property. Yes, we would stay again."
United States
Lisa
The price is CA $165
CA $192 total
includes taxes & fees
Mar 27 - Mar 28
Newly Furnished 1 Bedroom Apartment - Montego Bay
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

Top Wiltshire Hotel Reviews

Find out more about Wiltshire

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Wiltshire. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Wiltshire?

Yes, we have vacation rentals close to well known points of interest in Wiltshire, or you can select a more remote option if you're looking for relaxation. Wiltshire is known for its beaches and sporting events. Make sure you have time to check out the shopping and restaurants during your trip.

What are some of the best vacation rentals in Wiltshire?

Bev Rosevilla: You might want to consider this vacation rental near Wiltshire, which offers a terrace, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Wiltshire?

While exploring the area, visit family-friendly sights like Montego Bay Marine Park, or get outside and enjoy nature at Freeport Peninsula. In the larger area, you’ll find Montego Bay Cruise Ship Terminal and Saint James Parish Church.

What’s a vacation rental in Wiltshire like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Wiltshire. Vacation rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.