Winston Vacation Rentals from CA $120: Short-Term Rentals for 2026

Q: What are some of the best vacation rentals that Winston has to offer?

Houses and Grounds of Partridge Lodge : You might like this vacation home rental near Winston. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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Our top choices for Winston vacation rentals

A two-story building with a pointed roof and a sign reading "White Horse Inn."

1. The White Horse Inn

Eye

simon

CA $187 total

includes taxes & fees

Nov 12 - Nov 13

A round metal table with a white plate and two cups, surrounded by a wicker fence and potted plants.

2. a restful, rural retreat in beautiful Suffolk

Woodbridge

Stuart

CA $183 total

includes taxes & fees

Nov 17 - Nov 18

A view through a window of a brick house with a thatched roof, surrounded by lush greenery and blooming flowers.

3. Country Cottage Set In pretty Suffolk village with 2 local pubs, dog friendly

Lower Ufford

Alan S.

CA $248 total

includes taxes & fees

Nov 20 - Nov 21

A wooden house with a dark exterior, a wooden door, and a small window. There is a sign on the wall that reads "The Forge".

4. The Forge

Stowmarket

Ruskin

CA $980 total

includes taxes & fees

Nov 15 - Nov 16

An outdoor patio with a table and chairs, a sliding glass door leading to an interior space, and a wooden fence in the background.

5. What a lovely bolt hole.

Moats Tye, near Stowmarket

SUE ELWES

CA $271 total

includes taxes & fees

Nov 18 - Nov 19

An outdoor terrace with wicker tables and chairs, overlooking a marina with boats and buildings in the background.

6. Merchant Quarters, The Merchant House, Ipswich

Ipswich

CA $354 total

includes taxes & fees

Nov 13 - Nov 14

A nighttime outdoor patio area with a paved walkway, seating, and ambient lighting.

7. SPACIOUS 3 BED ROOM FAMILY FRIENDLY HOME CONVENIENTLY LOCATED IN IPSWICH SUFFOLK

Ipswich

Heather W.

CA $270 total

includes taxes & fees

Nov 13 - Nov 14

A wooden cabin with an open door, a bed, a chair, and a small table inside.

8. Cosy Glamping Cabin near Bury St Edmunds

Bury St Edmunds

Julia B.

CA $147 total

includes taxes & fees

Nov 15 - Nov 16

A room with exposed wooden beams, a bed with white bedding, two bedside lamps, and a folded towel on the bed.

9. 2 bedroom accommodation in Sproughton

Sproughton

Angela Harris

CA $430 total

includes taxes & fees

Nov 14 - Nov 15

A breakfast table set with breakfast items, a view of the outdoors, and a wooden deck.

10. Primrose 3 bed - Orchid - sleeps 6 guests in 3 bedrooms

Eye

Ella W.

CA $929 total

includes taxes & fees

Nov 23 - Nov 24

A room with a Christmas tree, a window with curtains, and a door.

11. Myrtle Cottage

Diss

Michael

CA $201 total

includes taxes & fees

Nov 13 - Nov 14

A window with a view of a brick building and greenery.

12. Pump Cottage

Orford

A wooden door leading to a courtyard with a stone wall and a white chair with a colorful cushion.

13. ❤️Seaside Fisherman Cottage❤️Aldeburgh⛱️

Aldeburgh

Nick

CA $587 total

includes taxes & fees

Nov 12 - Nov 13

A wooden door with a small window, a checkered curtain, and a tiled floor leading to a living room with a white sofa and a lamp.

14. The Bull Pen

Eye

CA $556 total

includes taxes & fees

Nov 27 - Nov 28

A grassy field with a circular structure in the foreground and a sunset in the background.

15. 3 bed Static Caravan With 5 Beds on a Holiday Park

Felixstowe

CA $183 total

includes taxes & fees

Nov 12 - Nov 13

A cozy living room with a fireplace, wooden furniture, and a television mounted on a brick wall.

16. Beautiful Grade ll newly renovated property, located in the heart of old Harwich

Harwich

Julian L.

CA $276 total

includes taxes & fees

Nov 14 - Nov 15

A rustic room with exposed wooden beams, a green sofa, a small table, and a window with curtains.

17. 1 Henham Barns, Henham Park, Nr Southwold, Suffolk NR34 8AQ, Oak framed style oasis in Country Suffo...

Beccles

John M.

CA $302 total

includes taxes & fees

Nov 12 - Nov 13

18. Luxury glamping with hot tub - Valley View Yurt

Sudbury

"I booked this stay for a birthday getaway for me and a couple of friends. It was so beautiful, the location was amazing just outside of a picturesque village. Everything we could need was provided. The beds were amazingly comfortable, the hot tub was exceptional and the communication from Charlie was excellent! Would 100% recommend to anyone looking at booking this place! Thank you for such an incredible stay"

Zoe P.

CA $286 total

includes taxes & fees

Nov 12 - Nov 13

A cozy living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with wooden cabinets and a window.

19. 3 bedroom accommodation in Saxmundham

Saxmundham

Opal D.

CA $846 total

includes taxes & fees

Nov 12 - Nov 13

A mobile home with a deck, outdoor seating, and a car parked in the background.

20. Ozeds Space Static Caravan Sleeps 6 With Indoor Pool

Felixstowe

CA $192 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Winston Hotel Reviews

The Four Horseshoes

Eye

10/10 Excellent

Hailea

An outdoor patio with wooden benches and tables, string lights, and potted plants.

Cherry Tree Pub

Woodbridge

10/10 Excellent

Janet

A dining area with brick walls, a fireplace, and a large window. Tables and chairs are arranged for dining.

The Railway

Ipswich

10/10 Excellent

Meagan

A bar area with a wooden ceiling, shelves of bottles, and bar stools.

The Crown hotel

Woodbridge

10/10 Excellent

Sarah

A buffet setup with various food items and serving utensils.

Mermaid, Ipswich by Marston's Inns

Ipswich

10/10 Excellent

Dan

A conservatory with a tiled roof, surrounded by a well-maintained garden with various plants and a lawn.

Toothbrush Rooms at Lattice Lodge

Ipswich

10/10 Excellent

Kathryn

A large brick building with multiple windows and a lawn in front.

Hintlesham Hall Hotel

Ipswich

10/10 Excellent

amanda

A dining area with a table set for two, a vase of flowers, and a view of the outdoors.

Hazel Barn B&B

Diss

10/10 Excellent

Doreen

Salthouse Harbour Hotel and Spa

Ipswich

10/10 Excellent

Caroline

A hotel reception area with a modern design, including a reception desk, a large mirror, and a decorative wall with a letter 'B'.

The Bell Hotel Saxmundham

Saxmundham

10/10 Excellent

Debbie

An outdoor patio area with wooden tables and chairs, shaded by large umbrellas, and a pathway leading to a building.

The Bull Inn

Bury St Edmunds

10/10 Excellent

Robin

Find out more about Winston

Everything you need to know about Winston 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 Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winston vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winston vacation rentals we have selected for you start as low as CA $120 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston 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 Winston 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 Winston 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 Winston. 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

Are there vacation rentals in Winston?

Yes, we have vacation rentals close to well known local attractions in Winston, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Winston has to offer?

Houses and Grounds of Partridge Lodge: You might like this vacation home rental near Winston. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

What can I see and do in Winston?

While exploring the area, visit family-friendly sights like Easton Farm Park, or get outside and enjoy nature at Helmingham Hall. In the larger area, you’ll find Framlingham Castle and The 95th Bomb Group Hospital Museum.

What are vacation rentals like in Winston?

Vacation rentals are privately owned properties you can book for a short or long stay in Winston. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for a small group gathering.

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Hadleigh Vacation Rentals
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Winston Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winston vacation rentals

1. The White Horse Inn

2. a restful, rural retreat in beautiful Suffolk

3. Country Cottage Set In pretty Suffolk village with 2 local pubs, dog friendly

4. The Forge

5. What a lovely bolt hole.

6. Merchant Quarters, The Merchant House, Ipswich

7. SPACIOUS 3 BED ROOM FAMILY FRIENDLY HOME CONVENIENTLY LOCATED IN IPSWICH SUFFOLK

8. Cosy Glamping Cabin near Bury St Edmunds

9. 2 bedroom accommodation in Sproughton

10. Primrose 3 bed - Orchid - sleeps 6 guests in 3 bedrooms

11. Myrtle Cottage

12. Pump Cottage

13. ❤️Seaside Fisherman Cottage❤️Aldeburgh⛱️

14. The Bull Pen

15. 3 bed Static Caravan With 5 Beds on a Holiday Park

16. Beautiful Grade ll newly renovated property, located in the heart of old Harwich

17. 1 Henham Barns, Henham Park, Nr Southwold, Suffolk NR34 8AQ, Oak framed style oasis in Country Suffo...

18. Luxury glamping with hot tub - Valley View Yurt

19. 3 bedroom accommodation in Saxmundham

20. Ozeds Space Static Caravan Sleeps 6 With Indoor Pool

Find vacation rentals that suit your style

Top Winston Hotel Reviews

The Four Horseshoes

10/10 Excellent

Find out more about Winston

Winston vacation rentals: An excellent choice for every season

How to find incredible deals on Winston rentals

Frequently Asked Questions

Are there vacation rentals in Winston?

What are some of the best vacation rentals that Winston has to offer?

What can I see and do in Winston?

What are vacation rentals like in Winston?

Explore a world of travel with Expedia