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Family-friendly vacation rentals in Oakham

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Oakham

  • Total vacation rentals

    Explore 30 vacation rentals in Oakham

  • Nightly prices starting at

    Oakham vacation rentals start at G$14,644 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Oakham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oakham rentals

  • 4.9 Average rating

    Oakham stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Oakham

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
The image captures a scenic view of a lush countryside landscape, featuring rolling green hills and dense trees. In the center, a charming yellow house is nestled amongst the greenery, surrounded by expansive fields and rich foliage under a partly cloudy blue sky.
Condo in Tilton on the Hill

The Hayloft: Popular Hideaway - Sleeps 3.

After our storming success for 6 years with our cosy Hayloft Apartment, we have totally refitted the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking [Now with EV Charging] a private patio for sunny breakfasts, lunches or sundowners. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details. The Welcome pack's a big hit.

4.9 out of 5 average rating, 198 reviews
Top guest favorite
Townhouse in Manton

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. The fenced garden has a shed and we welcome well-behaved dogs(£22 charge applies). Bedding and towels are included

4.99 out of 5 average rating, 187 reviews
Top guest favorite
A spacious outdoor dining area is set under a wooden pergola, adorned with colorful bunting. A large table is surrounded by eight chairs, with pink glasses and flower arrangements accenting the table. Guests are seen enjoying a barbecue in the scenic countryside backdrop.
Barn in Hallaton

Unique Countryside hideaway

Unique rural retreat perched on a hill in open countryside with breathtaking views. The Retreat is a self-contained 3 bedroom home adjacent to our barn conversion in 13 acres. The barn was converted by ourselves over two levels - one ground floor and one underground (don't worry it is very light and airy on the lower floor!) The perfect place for a countryside getaway to totally relax and unwind. Great walking and cycling on your doorstep or just switch off, chill out and enjoy the space.

4.97 out of 5 average rating, 140 reviews
Top guest favorite
The image showcases the exterior of Castle Garden Cottage, featuring red brick and whitewashed walls. A gravel path leads up to the entrance, framed by window boxes filled with flowers. The garden area displays lush greenery and is bordered by trees, providing a serene environment.
Cottage in Oakham

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, is located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

4.96 out of 5 average rating, 179 reviews
Guest favorite
A grassy outdoor space is bordered by neat hedges, contrasting with the lush green hills in the background. The bright sky features scattered clouds, enhancing the tranquility of the rural setting.
Tiny home in Empingham

Lower Farm View - Perfect For 2

Lower Farm View is beautifully converted with outstanding views, it's situated in the Rutland Village of Empingham and is only a short walk from Rutland Water's North Shore. Only 6 miles from the beautiful Georgian town of Stamford and 6/7 miles from the picturesque towns of Uppingham and Oakham. The village itself has a hairdresser, doctor's surgery, pub and shop. The local area has lots of pubs, cafes and shops. A perfect place to be able to enjoy and explore the county of Rutland.

4.84 out of 5 average rating, 347 reviews
Top guest favorite
The exterior of a stone barn conversion features a distinct pitched roof and a charming facade. The building is marked by weathered stonework and traditional details, including a chimney and a welcoming entrance, set against a clear blue sky.
Cottage in Empingham

Primrose Hall Holiday Cottage Rutland

Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, pub, medical centre, and an antique shop just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

4.99 out of 5 average rating, 195 reviews
Guest favorite
The kitchen features a double Belfast sink and handcrafted cabinetry, highlighted by warm, natural light filtering through the window. Exposed ceiling beams complement the neutral tones of the stylish design, while a potted plant adds a touch of greenery to the inviting space.
Condo in Uppingham

Central Character/Contemporary Apartment

Set within walking distance to Uppingham’s bustling town centre is this stunning central ground floor apartment full of character and original features creating an ultimate holiday experience. Guests will enjoy two spacious double bedrooms, built in wardrobe, hand crafted breakfast kitchen, exceptional shower room, subtle design touches and beautiful courtyard garden. Free parking is available 2-3min walk away from the property. There is also 2hrs free parking to the front.

4.91 out of 5 average rating, 129 reviews
Guest favorite
A charming thatched cottage exterior is framed by a gravel drive and manicured greenery. Large windows allow natural light to fill the interior, while a subtle mix of stone and thatched roofing contributes to the cottage's historic character.
Cottage in Wing

Idyllic Thatched Country Cottage - a hidden gem!

Situated in the picturesque village of Wing, this adorable thatched cottage is nestled in the grounds of beautiful Cedar House. The property was fully renovated in March 2021 and is the ideal getaway location to explore everything that stunning Rutland has to offer. The cottage is only 5 minute drive to Rutland Water, Uppingham and Oakham, so you have everything you wish to experience during your stay on your doorstep. Historic Stamford is also only 20 mins away.

4.86 out of 5 average rating, 369 reviews
Top guest favorite
A charming townhouse exterior is framed by neatly trimmed hedges, providing privacy. A light blue front door serves as a focal point, flanked by windows with shutters. Satellite dishes are mounted on the façade, enhancing the contemporary feel of the historic brick structure.
Townhouse in Oakham

Fennel House. Charming house in Oakham town centre

The townhouse is located on a quiet residential one way street. Oakham has stunning historical architecture, i.e a castle, quaint independent shops, pubs and restaurants are moments from the door. A short walk from the railway station. It is ideal for couples or families. A short drive is Rutland Water and is the largest man made lake in Europe 26 miles circumference and hosts many outdoor pursuits such as walking, cycling and bird watching.

4.95 out of 5 average rating, 367 reviews
Top guest favorite
A charming stone exterior of the cottage is visible, featuring several windows complementing the rustic facade. Flower pots with greenery are arranged along a gravel pathway, while a small bench provides a resting spot. Sunlight brightens the area, enhancing the inviting ambiance.
Cottage in Braunston-in-Rutland

Lovely Cottage In Pretty Village Nr Rutland Water

Gable Cottage is in the picturesque village of Braunston-in-Rutland. A unique two bedroom cottage annexe, with bath and shower. Dining room with kitchenette (air fryer, microwave, toaster, kettle), and cute gallery sitting area overlooking it. Access via private lane, parking for 2 cars. We also have an electric car charger Children over 10 welcome, no pets. Discount of £30 a night if only want one bedroom - message us before booking.

4.94 out of 5 average rating, 111 reviews
Top guest favorite
A cozy bedroom is showcased with a spacious bed and a bedside table featuring a warm lamp. A doorway leads to a stable where a black pony can be seen peering over a wooden barrier. Soft hay is visible in the stable area.
Farm stay in Thurgarton

Sleepover with Miniature horse Basil

Basils Barn is situated on the grounds of a 17th century manor, surrounded by a picturesque 60 acre estate. The bedroom is directly attached to Basils stable, where there is a doorway in between the two spaces. In the paddocks we also have a herd of Highland cows, Hebridean sheep, horses, pigs, chickens and Norwegian Forrest cats. Our animals are mostly rescued and all of our animals are kept strictly as pets.

4.95 out of 5 average rating, 450 reviews
Top guest favorite
The exterior of a charming converted barn is set against a clear blue sky. A gravel driveway leads to the entrance, bordered by neatly trimmed hedges. The structure features a mix of brick and wood finishes, with a covered entryway and green landscaping enhancing the rural setting.
Barn in Whissendine

Beautiful Conversion in Rutland Countryside

Come and stay in our lovingly converted barn in the middle of the Rutland countryside. Perfect for a quiet get-away with lots of walking and cycling from the doorstep. Set in a 3 acre plot of our family home, you will have access to a private garden at the rear of the property plus our orchard should you wish to bring 1 small - medium sized dog with you. Unfortunately, the property is not suited to large dogs.

4.99 out of 5 average rating, 183 reviews

Popular amenities for Oakham family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
Place to stay in South Croxton

Secluded Luxury Glamping pod & hot tub

4.96 out of 5 average rating, 144 reviews
Guest favorite
A green tractor is parked near a shelter on a farm, with people seated beneath the structure. The background features rolling hills and trees, creating a serene countryside setting.
Cabin in Harborough

Farm Stay Cabin at Windmill Farm

4.95 out of 5 average rating, 117 reviews
Superhost
Cottage in Bulby

Hot tub 4 bed RURAL Cottage sleeps 8 nr Stamford

4.85 out of 5 average rating, 176 reviews
Top guest favorite
Three relaxed alpacas are seated in a lush green paddock, surrounded by a wooden fence. In the background, a rustic green shepherd hut is visible, set against a cloudy sky and greenery.
Shepherd’s hut in Gilmorton

Hot tub, Aircon, firepit Horses Alpacas, pet pigs

4.96 out of 5 average rating, 583 reviews
Top guest favorite
The exterior of the Grade 2 listed Red Barn showcases traditional brickwork and a sloped roof with charming eaves. A pathway leads to the entrance, framed by lush greenery and a spacious lawn. The building features a balcony and large windows, enhancing natural light.
Home in Goadby Marwood

The Red Barn at Goadby Marwood - Hot Tub Sleeps 8+

4.99 out of 5 average rating, 109 reviews
Top guest favorite
A wood-clad cabin is nestled among trees, featuring rounded architecture and large windows. A wooden terrace with two chairs invites relaxation. A hot tub is positioned nearby, surrounded by nature and colorful autumn foliage.
Hut in Avon Dassett

Dassett Cabin - retreat, relax, romance, rewild

4.99 out of 5 average rating, 586 reviews
Top guest favorite
A large hot tub is housed in a separate garden building, featuring illuminated water jets that create soft ripples in the turquoise water. The surrounding area is designed for privacy, with subtle lighting enhancing the serene atmosphere.
Bungalow in Horbling

Garden Bungalow, Hot tub and Gazebo

4.97 out of 5 average rating, 206 reviews
Guest favorite
A rustic shepherd's hut is nestled amidst greenery, framed by willow trees. A grassy area with outdoor seating is visible in front, alongside a wood-burning stove contributing to a cozy atmosphere. Smoke gently rises into the air, suggesting warmth and comfort.
Shepherd’s hut in North Witham

Little Oaks at Hillview

4.98 out of 5 average rating, 348 reviews

Family- and pet-friendly home rentals

Guest favorite
A charming stone cottage with a red-tiled roof is surrounded by greenery. Large windows allow natural light to enter, while a small patio area with two metal chairs and potted plants sits in the foreground. The entrance features a dark wooden door.
Cottage in Rutland

Pantiles Cottage, Stretton, sleeps 4 self catering

4.89 out of 5 average rating, 215 reviews
Top guest favorite
A spacious kitchen features exposed wooden beams and stone flooring. A dining table with striped tableware is set for four, while modern appliances are arranged across the counters. Natural light floods in through multiple windows, illuminating the well-equipped cooking area.
Cottage in Duddington

Beautiful Grade II Listed Barn Conversion

4.99 out of 5 average rating, 253 reviews
Top guest favorite
The exterior of a charming 19th century barn is showcased, featuring a stone facade adorned with climbing wisteria. Two wooden doors frame the entrance, complemented by two symmetrical windows above. A gravel area leads up to the building, enhancing the quaint rural aesthetic.
Guesthouse in Clipsham

Spacious 2 bed barn conversion in Rutland

4.94 out of 5 average rating, 143 reviews
Guest favorite
An open plan suite features a king-sized bed with a plush headboard, complemented by a decorative quilt. A vintage grey wardrobe stands beside the freestanding bathtub, which is positioned near a large wall clock. Soft lighting enhances the serene atmosphere of the space.
Apartment in Rutland

Clock Cottage Self contained Rutland Rural Retreat

4.86 out of 5 average rating, 323 reviews
Guest favorite
The image captures a serene village scene, featuring charming stone cottages nestled among lush greenery. The majestic church tower rises in the background, adding architectural interest. A pathway winds gently through the area, inviting exploration of the picturesque surroundings.
Cottage in Ketton

Churchyard Ketton stone cottage next to the pub

4.94 out of 5 average rating, 166 reviews
Top guest favorite
A wooden glamping pod is viewed from the patio, which features outdoor seating and a fire pit. The pod has a curved roof and an entrance that opens to natural surroundings, with neatly maintained grass and a few shrubs adding to the peaceful rural setting.
Tiny home in Leicestershire

Cosy luxury glamping pod Rosina.

5.0 out of 5 average rating, 530 reviews
Top guest favorite
A charming stone cottage features a sloped roof and a staircase leading to double doors. The exterior, characterized by natural stone, is surrounded by neatly trimmed grass and garden paths, providing a welcoming approach to the entrance.
Guesthouse in Northamptonshire

The Old Telephone Exchange

4.93 out of 5 average rating, 467 reviews
Top guest favorite
A cozy outdoor area features a wooden swing under a pergola covered in vibrant green vines. Nearby, a small wooden table is accompanied by four chairs, framed by blooming flowers. Soft sunlight enhances the inviting, natural atmosphere.
Cabin in Melton Mowbray

Wooden cabin by river in rural Leicestershire.

4.9 out of 5 average rating, 273 reviews

Family-friendly home rentals with a pool

Top guest favorite
A view from an open window reveals a green meadow, where sheep graze peacefully. A stone wall borders the edge of the field, with trees and distant hills visible against the blue sky. Natural light filters softly into the space.
Barn in Drayton

Luxury apartment with outstanding views

4.94 out of 5 average rating, 128 reviews
Guest favorite
An indoor heated swimming pool is framed by large windows allowing natural light to fill the space. Exposed wooden beams add an architectural feature overhead, while a relaxed seating area is situated nearby, offering a view of the tranquil pool waters.
Home in Haceby

Private Indoor Pool | Countryside Retreat

4.9 out of 5 average rating, 338 reviews
Guest favorite
The exterior of a brick barn is shown, featuring a sloped roof with small skylights. A flight of stairs leads to the entrance. A parked vehicle is positioned to the side, with greenery and trees visible in the background against a cloudy sky.
Apartment in Lincolnshire

Gonerby Grange Farm Barn, Belton

4.91 out of 5 average rating, 106 reviews
Guest favorite
The lodge features a wooden exterior with a dark roof, set against a picturesque lakeside backdrop. A spacious deck extends from the lodge, inviting outdoor seating with views of the tranquil water and surrounding trees, enhancing the serene atmosphere.
Cabin in Tattershall

Fable Lodge | Lakeside Lodge with Hot Tub & Views

4.95 out of 5 average rating, 125 reviews
Guest favorite
The lounge area features a soft carpet and a decorative rug. A television is mounted on the wall, while a stylish cabinet with a mirror and storage sits opposite. Shelves hold books, adding a touch of personality to the space.
Cabin in Great Billing

2 Bedroom Caravan (sage) @ Billing Aquadrome

4.96 out of 5 average rating, 105 reviews
Top guest favorite
A charming entrance is framed by a rustic brick wall, adorned with climbing greenery. A distinctive black door leads into the building, which features a medieval-style knight figure beside it. A flag flutters above, adding a touch of character to the serene garden setting.
Tiny home in Warwick

Castle Folly- Unique castle experience for two

5.0 out of 5 average rating, 133 reviews
Top guest favorite
The living area features a spacious, light-filled space with large windows and exposed brick walls. A cozy sofa sits across from a round coffee table, surrounded by four contemporary chairs at a circular dining table. Decorative wall mirrors enhance the room's modern aesthetic.
Apartment in Loughborough

unique 2 bed apartment with pool & gym

4.98 out of 5 average rating, 259 reviews
Guest favorite
A modern lodge is set against a natural backdrop, featuring a wood exterior and expansive glass doors. The surrounding landscape includes green grass and trees, with a deck area visible, suggesting outdoor seating for relaxation.
Cabin in Bourn

Magdalene Lodge, Cambridge Country Club

4.96 out of 5 average rating, 220 reviews

When is the best time to visit Oakham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,962 GYDG$32,008 GYDG$34,937 GYDG$37,657 GYDG$40,795 GYDG$36,192 GYDG$40,795 GYDG$40,376 GYDG$39,330 GYDG$36,820 GYDG$34,937 GYDG$37,238 GYD
Avg. temp4°C5°C7°C9°C12°C15°C17°C17°C14°C11°C7°C5°C

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