Family-friendly holiday rentals in Oakham

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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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Guest favourite

Cottage in Cottesmore

4.98 out of 5 average rating, 109 reviews

Quiet Lane Retreat: The Bee Cottage Rutland

Welcome to our charming cottage located on a tranquil lane in Rutland. Just a quick 5-min drive from Rutland Water, this 17th-century cottage is a picture-perfect gem that has undergone a refurbishment. The thatched roof adds to its undeniable charm. Step inside and be greeted by original features like low ceilings, doorways and exposed beams, creating an authentic atmosphere.T he cottage comfortably accommodates up to 5 people, offering surprisingly spacious living. Enjoy free Netflix and WiFi.

27 Dec – 3 Jan

$477 NZD per night

Guest favourite

Cottage in Lincolnshire

4.95 out of 5 average rating, 357 reviews

Bresby Cottage, 3 Bedroom Country Cottage

Bresby Cottage is set in a rural farm location surrounded by private secure gardens. The Cottage is fully modernised and is a warm and comfortable. Comprises a cosy living room, fully fitted kitchen, electric oven and hob, fridge freezer, microwave and dishwasher. The washing machine and dryer are situated in the utility. There are two large bedrooms, one twin and a double, a third bedroom is situated off the double and can be utilised as a single bedroom/cot room or simply a dressing room.

7–14 Feb

$237 NZD per night

Guest favourite

Barn in King's Cliffe

4.83 out of 5 average rating, 337 reviews

2 large bedrooms sleeps 5 quiet farm location

My place is close to Stamford & Burghley House about 10 mins away. Off the A47 close to Wansford and the A1 . Its also close to Peterborough & Corby . 12 mins away. September come & relax. You can walk toFineshade woods and Rockingham Forest & the village of Kingscliffe ,straight from the farm . Lots of room for dogs & a secure garden at the back . The walking, biking is all off road. It has fantastic views and brilliant sunsets. The accommodation is all single story with spacious rooms.

20–27 Jul

$268 NZD per night

Guest favourite

Guesthouse in Hartford

4.96 out of 5 average rating, 281 reviews

The Orchard Chalet superb amenities total privacy

Private space own entrance, in quiet residential area. Private guest parking. Enhanced cleaning procedure carried out prior to your stay. Relaxing and a great location with lots of extras for a comfortable stay. Perfect for professionals. Great base for Cambridge visits. Friendly local pubs, walks and cruises on the River Ouse. Hinchingbrooke Country Park hosts park runs, walks and woodland events with lots of outdoor activities. The area has Mills and great tea rooms, pubs and restaurants.

13–20 Oct

$132 NZD per night

Guest favourite

Farm stay in Rutland

4.93 out of 5 average rating, 123 reviews

The Old Stables Retreat, Northfield Farm

Quiet, romantic retreat on small family-run working farm w. rare & native breed cattle & sheep. Fascinating place to learn about food & the countryside. Great place to stay & explore one of England's most lovely countryside areas. Farm shop, open for 20 + yrs, sells a wide range of home grown & home butchered meats & local flour, beers, ready meals & pies. Nr. Rutland Water, & Melton Mowbray, of pie fame, Stamford & Leicester. Great pubs abound, as do walks & entertainment of every kind.

13–20 Mar

$238 NZD per night

Guest favourite

Condo in Tilton on the Hill

4.89 out of 5 average rating, 114 reviews

The Hayloft: popular hideaway - sleeps 3

After our storming success for 6 years with our cosy Hayloft Apartment, we have now totally refurbished the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking with a private patio for sunny breakfasts, lunches or sundowners at the freshly refurbished Hayloft. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details

26 Jan – 2 Feb

$152 NZD per night

Guest favourite

Cottage in Rutland

4.93 out of 5 average rating, 116 reviews

Daphne's cottage

Our comfortable stone built self-contained cottage, situated 1/2 mile from the A1 in a rural village called Stretton. The cottage contains .. 2,Bedrooms .. room 1 with a double bed and room 2, with 2 single beds (which are "Zip and link beds") by request can be turned in to a King size bed. shower room .. with a large comfortable shower cubicle (unfortunately no bath) a front room and fully equipped kitchen. You also have your own private Patio area.

16–23 Feb

$242 NZD per night

Guest favourite

Guesthouse in Barrow upon Soar

4.92 out of 5 average rating, 249 reviews

Spacious Annexe in Riverside Village

A modern annexe with a private entrance. Open plan living space (inc. pool table), fully equipped kitchen, 2 bedrooms and bathroom. Well Serviced village (train station, pubs, restaurants and shops). On the picturesque River Soar (walks, canoeing, boating and more. Part of a family home. ** PLEASE NOTE. We have two friendly dogs who live here so if you are frightened of dogs or don’t like them please consider this prior to booking.

25 Nov – 2 Dec

$212 NZD per night

Guest favourite

Home in Stamford

4.97 out of 5 average rating, 245 reviews

Detached Victorian Cottage, Stamford

The cottage is located on a private lane with free parking. Stamford's stunning historic architecture, quaint independent shops and fabulous pubs are moments from the door. Short walk from the railway station. The cottage is ideal for a couple or group of 3. Being in town, there are daytime background noises of a a nearby laundry and occasional workman in the area but people don't generally find these a problem.

18–25 Jan

$170 NZD per night

Guest favourite

Loft in Stainby

4.94 out of 5 average rating, 159 reviews

Studio in quiet countryside setting

This self contained, open plan studio sleeps two in either two single or one kingsize bed(s). As a matter of course, the bed is always made up as super king size, so if you would prefer two singles please request at time of booking. There is a separate shower room and small kitchen area with small fridge and mini oven and hob. Situated in a delightful countryside setting between Stamford and Grantham.

13–20 Jan

$146 NZD per night

Guest favourite

Cabin in Harby

4.97 out of 5 average rating, 256 reviews

Self contained Oak Framed Studio in Village garden

Situated in the Vale of Belvoir, this self-contained, open plan studio sleeps two people comfortably and includes a fully equipped kitchen, shower room, high speed Wifi and Smart TV. Surrounded by countryside, Harby is ideal for walking, cycling and being in the great outdoors. There are an abundance of public footpaths in the Vale and we can provide plenty of inspiration and maps!

29 Nov – 6 Dec

$145 NZD per night

Guest favourite

Apartment in Ketton, Stamford, Lincs

4.94 out of 5 average rating, 295 reviews

Private Apartment in the Heart of Ketton, Stamford

Relax and unwind in the spacious, private apartment with garden in the beautiful village of Ketton. Close to Stamford, Rutland Water and Burghley House. One double bed plus one sofa bed (sleeps 2) in open plan apartment with fully fitted kitchen and private bathroom. 3 miles to the A1 / 4 miles Stamford / 20 mins Peterborough with direct trains to London Kings Cross (50 mins).

17–24 Sep

$182 NZD per night