Vacation rentals in Annan

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Top-rated vacation rentals in Annan

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Guest favorite
A spacious garden area is shown, featuring a mix of lawn and seated areas. Wooden benches are arranged around a small table, and a nearby building provides a shaded spot. A backdrop of red brick houses and greenery is visible under clear skies.
Cottage in Powfoot
4.92 out of 5 average rating, 100 reviews

Beach, Period 3 Bed Cottage with Great Kitchen

Ideal for the family or trips with friends, our period cottage is beautifully situated directly overlooking an Arts and Crafts style Bowling Pavilion and the large beach immediately beyond. The house sleeps 6 in 3 bedrooms, has a big well-equipped kitchen, wi-fi and a comfy lounge with a wood and coal burning fire. Relax or find an adventure. Powfoot is peaceful with a bar and restaurant. There's free putting at the door, golf, lots of nature, nearby outlet shopping, the Solway coast and more!

Top guest favorite
A quaint bothy is nestled amidst vibrant greenery and flowering plants. The rustic stone structure features a sloped roof and green door, surrounded by well-maintained garden beds. Wood stacks are visibly arranged beside the building, with trees offering a natural canopy overhead.
Tiny home in Dumfries and Galloway
4.95 out of 5 average rating, 311 reviews

Comfy bothy set in a beautiful scenic garden

Craigieburn garden bothy is a glamping-type single room bothy in a lovely 6-acre garden in beautiful Moffatdale, a great location for walkers and cyclists. The garden has woodlands, waterfalls, wildlife and exceptional planting for you to roam in. The bothy has no mains water or electricity so is a real alternative experience, with separate flush toilet and washing facilities. Otherwise all home comforts are provided with double bed, kitchenette and wood-burning stove to create a cosy atmosphere

Top guest favorite
A bright bedroom showcases large windows offering views of open fields. A cozy double bed with plaid bedding is positioned beside a bedside table with a lamp. A comfortable chair and a small side table create an inviting corner for relaxation. Greenery adds a touch of nature.
Home in Cummertrees
4.92 out of 5 average rating, 168 reviews

Queensberry Terrace - spacious & cosy

Situated between Carlisle & Dumfries - we are in the ideal place for a stop-over or half way holiday. We are lucky to boast on the fact we are so close to beautiful wedding hotspots. Kinmount House is 2.4 miles away & Gretna Green is only 12 miles away. We are with-in walking distance to Powfoot beach & the golf course. The closest town is Annan. Taxis are easy & quick if required, also the bus stop is outside. Our place is ideal for families & we welcome well behaved, housetrained doggies too!

Guest favorite
Tiny home in Gretna
4.91 out of 5 average rating, 329 reviews

Annex Retreat, sleeps 2 near Gretna, M6Jct45 / A75

The Retreat @ Solway House is a cosy 1-bed annex tucked away in our garden in the peaceful hamlet of Rigg, just 1 mile from Gretna Green. Our semi rural location is only a 3 mile drive from the M6/and just off the A75, the perfect stop over to break up any car journey, we provide parking for one car on our driveway. The Annex is a self-contained tiny home with its own private entrance, featuring a double bed, log burner, cosy sofa area, shower room, and a fully equipped kitchen/dining area.

Top guest favorite
A wooden cabin is showcased with an arched roof and large glass double doors. Two chairs are positioned on a covered porch, overlooking a well-maintained grassy area enclosed by wooden fencing. Trees and open fields are visible in the background.
Guesthouse in Dumfries and Galloway
4.99 out of 5 average rating, 404 reviews

Sea Views-Scotland-Cluaran Cabins-Solway Breeze

With views over looking the solway shore onto the beautiful mountains in Lake District, we offer this self catering cabin, with your own private and secure garden for any four legged friends you may wish to bring with you. Situated in a rural location with amazing walks on your doorstep. Our local town amenities are within a 2mile walk or 5minute drive. There are many tourist attractions near by that can either be reached by car, bus or train. This accommodation offers something for everybody.

Top guest favorite
A cozy living and dining area is depicted, featuring a comfortable grey sofa with textured cushions. A wooden dining table for four is visible near the window, which allows natural light to brighten the space. Decorative plants enhance the inviting ambiance.
Apartment in Dumfries and Galloway
4.99 out of 5 average rating, 104 reviews

Mains Street Retreat

Enjoy a stylish experience at this centrally-located place in Lockerbie. Possibly the only self-catering apartment available in the region for 1 night or multi night stays. All amenities under a 3 min walk, trains, supermarket, shops, cafes, pubs, bistro, gift & antique shops. Great location to explore Dumfries & Galloway, Southern Uplands, Solway Firth, Borders, Hadrians Wall, Lochs, Forests, waterfalls, Nature reserves, Castles, Museums, biking and water sports. Welcome pack, Pet Friendly.

Top guest favorite
The entrance gate opens to a wooden decking area, framed by slim exterior walls. Lush green plants are visible, with a glimpse of the summerhouse doorway in the background, leading to the interior space.
Place to stay in Annan
4.93 out of 5 average rating, 182 reviews

Delightful summerhouse studio with hot tub

Set in the garden of an old sandstone farmhouse this summerhouse offers a relaxing getaway with views over the Cumbrian hills and beautiful shoreline walks. Set just on the outskirts of the town of Annan you have access to all local amenities within a mile radius. Accommodation comprises of sofa bed (double), kitchenette with microwave, toaster, kettle and shower room. Lovely wood fuelled hot tub included. The property offers off-road parking and is dog friendly (please add to booking).

Top guest favorite
The interior of a handcrafted lodge features a curved wooden ceiling, creating a cozy atmosphere. A spacious bed with patterned bedding is positioned beside a small dining table and stools. Large glass doors open to an outdoor area, while light filters through the window.
Cabin in Clarencefield
4.94 out of 5 average rating, 156 reviews

Woodpeckers lodge

Escape to our newly handcrafted self contained woodland lodge set in peaceful clarencefield 10 mins from Annan / Dumfries we accomadate 2 adults one infant up to 5 on cozy put up bed stunning woodland walks wildlife few steps away charming country pub good food few hundred metres away also provide local beauty treatments and make up for weddings close by come visit us for few nights to recharge those batteries and relax with everything you need for your break away in beautiful countryside

Top guest favorite
The entrance features a bright yellow door framed by two decorative topiary plants in square pots. Flanking the door are two windows with white frames, allowing natural light to enhance the warm tones of the stone exterior.
Cottage in Halleaths
5 out of 5 average rating, 240 reviews

Converted Stables - Scenic 'Courtyard Cottage'

'Courtyard Cottage' is situated in a courtyard - previously stables and tastefully converted to a high standard. Easy driving distance of the A74(M), with good rail & bus links. The cottage provides the ideal base to enjoy the many cultural and outdoor activities available in the area. Plenty of lovely walks, sailing, fishing, wild life and great night skies. Perfect to kick back and relax after a day of exploring the many attractions and scenery. parking is available.

Top guest favorite
An open living space features a yellow sofa and various seating options surrounding a round dining table. A staircase with black railings leads to an upper level, while a large screen television is mounted on the wall. Natural light filters through the windows, highlighting the modern décor.
Barn in Annan
5 out of 5 average rating, 236 reviews

Annan, Dumfries & Galloway, Scotland Barn - 2 Bed

Watchhall Annexe is a recently converted barn, situated on the edge of the Royal Burgh Town of Annan. Attached to Watchhall House, it overlooks the Solway Firth and has views of the Lake District hills. It is within a 10-minute drive of the M6/M74 corridor on the Scottish-England border at Gretna. The area boasts lots of lovely places to eat and relax. Ideal for walking and cycling. Gretna Gateway Outlet Village and famous wedding venue is just a 10-minute drive away.

Superhost
The entrance features a secure, glass-paneled door set within a brick facade. Potted greenery is placed on either side of the entrance, complementing the polished black floor tiles that lead inside.
Condo in Cumbria
4.86 out of 5 average rating, 779 reviews

Pow Maughan Studio Apartment Mews @ Wheelbarrow

Pow Maughan Studio apartment at Mews Wheelbarrow has a single entrance and is a completely self contained studio within the building with high levels of security, external CCTV. The studio has a King Size bed with super comfy mattress and two high quality single Z beds. The apartment has its own shower/toilet/sink and the specification is of an exceptional standard. The studio is Smart lock accessible guests do not require keys. Super fast 80/20 speed WiFi

Top guest favorite
A spacious lounge area features two leather sofas, accent pillows, and a wooden coffee table on a light rug. Exposed wooden beams create an open atmosphere, while warm lighting fixtures enhance the bright space, which connects to the dining area in the background.
Cottage in Dumfries and Galloway
5 out of 5 average rating, 116 reviews

DISTILLERY(The Stables) with private HOT TUB

*SPECIAL OFFER* 2 NIGHT WEEKEND BREAKS BETWEEN FRI. 21st NOV. 2025 - MON. 30th MARCH 2026. Get in touch for details. Distillery Luxury Holiday Cottages are situated in a unique position nestled between our own Distillery Stud and the Annandale Distillery(the First or Last in Scotland)Spacious sandstone stable conversions completed to v high standard in October 15.

Popular amenities for Annan vacation rentals

When is the best time to visit Annan?

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Avg. priceR1,833 ZARR1,559 ZARR1,593 ZARR1,816 ZARR1,987 ZARR2,038 ZARR2,193 ZARR2,124 ZARR1,953 ZARR1,867 ZARR1,610 ZARR1,867 ZAR
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Annan?

    Annan has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Annan?

    Four-legged friends are welcome in Annan. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Annan?

    Yes! Work meets play with ease at over 10 vacation rentals in Annan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Annan?

    Make yourself at home in Annan by choosing from our most frequently booked neighborhoods. We have over 80 vacation rentals in Annan, and over 80 vacation rentals in Howes.

Quick stats about vacation rentals in Annan

  • Total vacation rentals

    Explore 20 vacation rentals in Annan

  • Nightly prices starting at

    Annan vacation rentals start at R685 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Annan vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Annan rentals

  • 4.7 Average rating

    Annan stays receive an average rating of 4.7 out of 5 from guests

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  5. Annan